Biotin

Identification

Summary

Biotin is a B-complex vitamin found in many multivitamin products.

Brand Names
Concept Ob, Infuvite, Infuvite Pediatric, Irospan 24/6 Kit, Mvi Pediatric
Generic Name
Biotin
DrugBank Accession Number
DB00121
Background

A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 244.311
Monoisotopic: 244.088163078
Chemical Formula
C10H16N2O3S
Synonyms
  • (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid
  • (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid
  • 5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
  • Biotin
  • Biotina
  • Biotine
  • Biotinum
  • cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid
  • cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
  • cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid
  • Coenzyme R
  • D-(+)-biotin
  • D-Biotin
  • Vitamin B7
  • Vitamin H

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to preventVitamin deficiency•••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Biotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring, which attaches a valeric acid substituent at one of its carbon atoms. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.

Mechanism of action

Biotin is necessary for the proper functioning of enzymes that transport carboxyl units and fix carbon dioxide, and is required for various metabolic functions, including gluconeogenesis, lipogenesis, fatty acid biosynthesis, propionate metabolism, and catabolism of branched-chain amino acids.

TargetActionsOrganism
UPropionyl-CoA carboxylase beta chain, mitochondrial
cofactor
Humans
UBiotin--protein ligase
substrate
Humans
UMethylcrotonoyl-CoA carboxylase beta chain, mitochondrial
cofactor
Humans
UAcetyl-CoA carboxylase 2
cofactor
Humans
UMethylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial
cofactor
Humans
UPyruvate carboxylase, mitochondrial
cofactor
Humans
UPropionyl-CoA carboxylase alpha chain, mitochondrial
cofactor
Humans
UAcetyl-CoA carboxylase 1
cofactor
Humans
Absorption

Systemic - approximately 50%

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Prolonged skin contact may cause irritation.

Pathways
PathwayCategory
Biotin MetabolismMetabolic
2-Hydroxyglutric Aciduria (D and L Form)Disease
3-Hydroxy-3-methylglutaryl-CoA Lyase DeficiencyDisease
Malonic AciduriaDisease
Methylmalonic AciduriaDisease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Lactic AcidemiaDisease
Primary Hyperoxaluria Type IDisease
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDisease
Transfer of Acetyl Groups into MitochondriaMetabolic
Isobutyryl-CoA Dehydrogenase DeficiencyDisease
Congenital Lactic AcidosisDisease
Fumarase DeficiencyDisease
Mitochondrial Complex II DeficiencyDisease
2-Ketoglutarate Dehydrogenase Complex DeficiencyDisease
Fructose-1,6-diphosphatase DeficiencyDisease
Triosephosphate IsomeraseDisease
Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Warburg EffectMetabolic
The Oncogenic Action of 2-HydroxyglutarateDisease
Valine, Leucine, and Isoleucine DegradationMetabolic
Alanine MetabolismMetabolic
3-Methylglutaconic Aciduria Type IIIDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDisease
Propionic AcidemiaDisease
3-Methylcrotonyl-CoA Carboxylase Deficiency Type IDisease
Isovaleric AciduriaDisease
Pyruvate Carboxylase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Avoid dietary avidin (a glycoprotein in uncooked egg-whites). Avidin binds with biotin in the gastrointestinal tract preventing biotin absorption. Avidin is denatured by cooking; therefore, cooked egg whites do not reduce biotin absorption.

Products

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Product Images
International/Other Brands
Appearex / Biodermatin / Bioepiderm / Meribin / Nail-ex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Spai-sons Prolac-vitLiquid0.01 mg/100mLTopicalSpai Sons Pharmaceutical International Cosmetics2012-08-06Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Acti-biotin 300 Caplet 300mcgTablet300 mcgOralActi Form Ltd.1991-12-312005-03-21Canada flag
ASCE plus Scalp Care HRLVPowder0.01 mg/20mgTopicalExocobio Inc.2021-10-01Not applicableUS flag
Biona-vit Controls and Prevents Hair LossLiquid0.01 mL/100mLTopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUS flag
Biotin 300 Mcg - TabletTablet300 mcgOralHealth Wise Nutrition Inc.1996-10-222002-07-18Canada flag
Biotin 300 Mcg TabletTablet300 mcgOralGeneral Nutrition Canada Inc.1997-04-182005-08-05Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
24 Multivitamins + MineralsBiotin (25 mcg) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Calcium (130 mg) + Cholecalciferol (400 unit) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Cyanocobalamin (25 mcg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-04-302002-07-31Canada flag
50 PlusBiotin (20 mcg) + Ascorbic acid (200 mg) + Choline bitartrate (20 mg) + Cyanocobalamin (20 mcg) + Folic acid (.2 mg) + Inositol (20 mg) + Niacin (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (20 mg) + Riboflavin (20 mg) + Thiamine hydrochloride (20 mg) + Vitamin A palmitate (10000 unit) + Vitamin D (400 unit) + Vitamin E (20 unit)TabletOralQuest Vitamins A Div Of Purity Life Health Products1998-08-042001-07-06Canada flag
50 Plus Multiple Vitamins & MineralsBiotin (45 mcg) + Ascorbic acid (90 mg) + Calcium (200 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg)TabletOralGfr Pharma Ltd.2002-10-202004-06-15Canada flag
574H Cell CareBiotin (0.18 g/300mL) + Nicotinamide (0.9 g/300mL) + Panthenol (1.5 g/300mL) + Pyrithione zinc (3.0 g/300mL)ShampooTopicalCelino Inc.2020-06-01Not applicableUS flag
Adeks - DpsBiotin (15 mcg / mL) + Ascorbic acid (45 mg / mL) + Beta carotene (1 mg / mL) + Cyanocobalamin (4 mcg / mL) + Nicotinamide (6 mg / mL) + Panthenol (3 mg / mL) + Phylloquinone (0.1 mg / mL) + Pyridoxine hydrochloride (0.6 mg / mL) + Riboflavin (0.6 mg / mL) + Thiamine (0.5 mg / mL) + Vitamin A palmitate (1500 unit / mL) + Vitamin D (400 unit / mL) + Vitamin E (40 unit / mL) + Zinc sulfate (5 mg / mL)Solution / dropsOralAxcan Pharma1995-12-312007-10-01Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
574H Cell CareBiotin (0.18 g/300mL) + Nicotinamide (0.9 g/300mL) + Panthenol (1.5 g/300mL) + Pyrithione zinc (3.0 g/300mL)ShampooTopicalCelino Inc.2020-06-01Not applicableUS flag
Anti Hair LossBiotin (0.06 g/100g) + Pyrithione zinc (2.1 g/100g)SoapTopicalGolden B America, Llc.2018-03-13Not applicableUS flag
ASCE plus Scalp Care HRLVBiotin (0.01 mg/20mg)PowderTopicalExocobio Inc.2021-10-01Not applicableUS flag
BacminBiotin (150 ug/1) + Ascorbic acid (500 mg/1) + Chromium Cr-51 chloride (0.1 mg/1) + Cupric oxide (3 mg/1) + Cyanocobalamin (50 ug/1) + Ferrous fumarate (27 mg/1) + Flavone (50 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (50 mg/1) + Manganese gluconate (5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (25 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (20 mg/1) + Selenomethionine (50 ug/1) + Thiamine mononitrate (20 mg/1) + Vitamin A acetate (2000 [iU]/1) + Zinc oxide (22.5 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralMarnel Pharmaceuticals, Llc2000-04-01Not applicableUS flag
Biona-vit Controls and Prevents Hair LossBiotin (0.01 mL/100mL)LiquidTopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUS flag

Categories

ATC Codes
A11HA05 — Biotin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Biotin and derivatives
Sub Class
Not Available
Direct Parent
Biotin and derivatives
Alternative Parents
Imidazolyl carboxylic acids and derivatives / Medium-chain fatty acids / Thia fatty acids / Heterocyclic fatty acids / Thiolanes / Imidazolines / Isoureas / Azacyclic compounds / Carboximidamides / Carboxylic acids
show 7 more
Substituents
2-imidazoline / Aliphatic heteropolycyclic compound / Azacycle / Biotin / Carbonyl group / Carboximidamide / Carboxylic acid / Carboxylic acid derivative / Dialkylthioether / Fatty acid
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
biotins (CHEBI:15956) / Water-soluble vitamins (C00120)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6SO6U10H04
CAS number
58-85-5
InChI Key
YBJHBAHKTGYVGT-ZKWXMUAHSA-N
InChI
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
IUPAC Name
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
SMILES
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2

References

Synthesis Reference

Takayoshi Mitsunaga, Kiyoto Chinushi, Tadashi Umezu, "Water-soluble biotin-containing preparation." U.S. Patent US4277488, issued May, 1940.

US4277488
General References
  1. Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. [Article]
Human Metabolome Database
HMDB0000030
KEGG Drug
D00029
KEGG Compound
C00120
PubChem Compound
171548
PubChem Substance
46508694
ChemSpider
149962
BindingDB
12
RxNav
1588
ChEBI
15956
ChEMBL
CHEMBL857
ZINC
ZINC000035024346
PharmGKB
PA448625
PDBe Ligand
BTN
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Biotin
PDB Entries
1avd / 1bdo / 1bib / 1df8 / 1f27 / 1hxd / 1kqs / 1luq / 1mep / 1mk5
show 112 more
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)1
4TerminatedTreatmentMyocardial Stunning1
4Unknown StatusTreatmentHyperuricemia1
3Active Not RecruitingTreatmentModerate Persistent Asthma1
3RecruitingTreatmentAcute Decompensated Heart Failure (ADHF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • 21st Century Healthcare Inc.
  • Amend
  • Ivax Pharmaceuticals
  • Magno-Humphries Laboratories
  • Mason Distributors
  • Mckesson Corp.
  • Medisca Inc.
  • Merz Pharmaceuticals LLC
  • Nutrition 21 Inc.
Dosage Forms
FormRouteStrength
TabletOral300 mcg
Tablet, chewableOral2500 ug/1
SoapTopical
SolutionIntravenous1.914 mg
SolutionOral
Tablet, delayed releaseOral
TabletOral
Granule, effervescent20 MG
Granule, effervescent5 MG
Injection, solution5 MG/1ML
TabletOral5 MG
LiquidTopical0.01 mL/100mL
TabletOral500 mcg
CapsuleOral500 mcg / cap
Tablet, extended releaseOral1 mg / tab
Capsule, liquid filledOral2500 ug/1
TabletOral250 mcg
TabletOral300 mcg / tab
LiquidTopical0.002 mL/1mL
ShampooTopical
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
TabletOral5 mcg / tab
Tablet, film coated
Tablet
Capsule
Injection, solution
PowderTopical
LiquidTopical
Tablet, chewableOral
PowderTopical0.01 mg/20mg
Solution / dropsOral
Tablet, extended releaseOral
CreamTopical0.1 g/100g
LiquidTopical0.0001 g/100mL
ShampooTopical0.06 mL/100mL
SolutionTopical0.06 mL/100mL
Kit; tablet; tablet, film coatedOral
Tablet, effervescentOral
Injection, solution, concentrate; kitIntravenous
Injection, powder, lyophilized, for solutionIntravenous
KitIntravenous
SprayTopical
SolutionIntravenous
SyrupOral
LiquidIntravenous
CapsuleOral
Capsule, liquid filledOral
Tablet, orally disintegratingOral
Gum, chewingOral
Powder
Injection, solution; kitIntravenous
Injection, solutionIntravenous
Capsule, liquid filled; kit; tablet, coatedOral
Capsule, gelatin coatedOral
PillOral
LiquidOral
Liquid; tabletOral
Powder, for solutionIntravenous
SolutionParenteral
Injection, powder, for solutionIntravenous100 mg
LiquidTopical0.01 mg/100mL
CreamTopical0.1 g/10g
CreamTopical0.07 g/0.7g
Syrup
Capsule, extended releaseOral
Powder, for solutionIntramuscular; Intravenous
Powder, for solutionOral
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous
Tablet, film coatedOral
Tablet, coatedOral
TabletOral
KitOral
PowderOral
Tablet, film coated0.6 mg
TabletOral1 mg
TabletOral0.6 mg
CapsuleOral0.6 mg
Prices
Unit descriptionCostUnit
Biotin powder14.69USD g
D-biotin powder12.0USD g
Diachrome capsule0.29USD capsule
Appearex 2.5 mg tablet0.26USD tablet
Stress b tablet0.1USD tablet
Stress 600 tablet0.08USD tablet
Biotin 800 mcg tablet0.06USD tablet
Biotin 300 mcg tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)232 dec °CPhysProp
water solubility220 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP0.17ALOGPS
logP0.32Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4Chemaxon
pKa (Strongest Basic)-1.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area78.43 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity60.05 m3·mol-1Chemaxon
Polarizability24.92 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7395
Blood Brain Barrier+0.9383
Caco-2 permeable-0.7206
P-glycoprotein substrateSubstrate0.6413
P-glycoprotein inhibitor INon-inhibitor0.9561
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.8803
CYP450 2C9 substrateNon-substrate0.7602
CYP450 2D6 substrateNon-substrate0.7872
CYP450 3A4 substrateNon-substrate0.6911
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9252
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9762
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9598
BiodegradationNot ready biodegradable0.8923
Rat acute toxicity2.0581 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9596
hERG inhibition (predictor II)Non-inhibitor0.9145
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.84 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f76-1960000000-b21ddd69490cac3254f8
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0f76-3960000000-a8a94e2de123f66979d8
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-6910000000-11bfe0a5a77f7dfaa8c5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f76-1960000000-b21ddd69490cac3254f8
GC-MS Spectrum - GC-MSGC-MSsplash10-0f76-3960000000-a8a94e2de123f66979d8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0006-0090000000-6d956bb533d353d449c9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-0190000000-01f67d1bdf8c742e48c8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0fxx-3920000000-f0b9613cbd9371e4be92
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9400000000-107f2a44f521c2513578
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-1a3f65d909dc40055e87
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-004i-0090000000-c928e8d0a18f3f848262
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-066s-1920000000-5f795e0b7f1d7cf986e5
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0ar1-1920000000-c298be862857cb3bbc7f
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000t-0900000000-cdc4a4c359ff765fd32d
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-05xs-1920000000-3be430b63e9c748c681a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0090000000-bcffb0dcf77e8fd727a4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0f6x-0390000000-c209523d36e9a7681f44
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0090000000-c0f81ee86772310db415
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0190000000-016eb89528e564c74720
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0fxx-3920000000-f0b9613cbd9371e4be92
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9400000000-107f2a44f521c2513578
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-d08e1b3709844e1e91b0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0190000000-21d0f2512788276bbb89
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0690000000-dc372934024e58bdcc60
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0790000000-3dc732a115953d99a259
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9000000000-0dcf3287376f08cde6b9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9000000000-fb6f5d6679dea0ec8f1b
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-1090000000-a44a68df615196a327c9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-1090000000-2e33eb7d14f0f9ca9150
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0090000000-f48642f6233836198f74
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0090000000-76deccfabe183e0493ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-002b-0090000000-3cb9f7103e4e1c5acb62
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-ce581561c6acbdbbd1f5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0940000000-54c1616d9935143625fc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-060a-1900000000-11a5d4190980b5a6935f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-074j-2900000000-e841b569650afc851aa0
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-004i-0090000000-5b10fe54708d7ca5c408
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-1590000000-a16a26fc2f2cb15db60f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05bb-0090000000-4acb49d8f6dd27ef371f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-d49f9fcc9039367efbdf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-e33611580a206e3bea79
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05bb-0090000000-88e1ac3f0b5053c20229
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0090000000-e7a8a723fba0a18a4f06
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0090000000-10bd2f9f4f19b0e117b6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014l-0090700000-cd3e4fbf4459f0f16e33
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014l-0090800000-eeb273d2eaf881339ed0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05xs-1920000000-3be430b63e9c748c681a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0090000000-83187c55c7a9f5fa491e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-c807b815144ca7c795b9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0290000000-330c002d740b15dff5d8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-3490000000-31752d046b2f936cd677
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uei-1920000000-f1a84df09a75c73a5987
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-5910000000-f91a4f930a7db10593a7
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.6796407
predicted
DarkChem Lite v0.1.0
[M-H]-147.4872583
predicted
DarkChem Standard v0.1.0
[M-H]-159.3883407
predicted
DarkChem Lite v0.1.0
[M-H]-160.8116407
predicted
DarkChem Lite v0.1.0
[M-H]-155.1844407
predicted
DarkChem Lite v0.1.0
[M-H]-155.23927
predicted
DeepCCS 1.0 (2019)
[M+H]+160.1954407
predicted
DarkChem Lite v0.1.0
[M+H]+159.8638407
predicted
DarkChem Lite v0.1.0
[M+H]+159.3677407
predicted
DarkChem Lite v0.1.0
[M+H]+160.0886407
predicted
DarkChem Lite v0.1.0
[M+H]+155.8402407
predicted
DarkChem Lite v0.1.0
[M+H]+157.59727
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.8999407
predicted
DarkChem Lite v0.1.0
[M+Na]+159.7918407
predicted
DarkChem Lite v0.1.0
[M+Na]+158.3839407
predicted
DarkChem Lite v0.1.0
[M+Na]+160.0666407
predicted
DarkChem Lite v0.1.0
[M+Na]+164.49681
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Propionyl-coa carboxylase activity
Specific Function
Not Available
Gene Name
PCCB
Uniprot ID
P05166
Uniprot Name
Propionyl-CoA carboxylase beta chain, mitochondrial
Molecular Weight
58215.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [Article]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [Article]
  5. Ishii M, Chuakrut S, Arai H, Igarashi Y: Occurrence, biochemistry and possible biotechnological application of the 3-hydroxypropionate cycle. Appl Microbiol Biotechnol. 2004 Jun;64(5):605-10. Epub 2004 Feb 28. [Article]
  6. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Enzyme binding
Specific Function
Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl-CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-meth...
Gene Name
HLCS
Uniprot ID
P50747
Uniprot Name
Biotin--protein ligase
Molecular Weight
80759.345 Da
References
  1. Velazquez-Arellano A: From an inborn error patient to a search for regulatory meaning: a biotin conducted voyage. Mol Genet Metab. 2006 Mar;87(3):194-7. Epub 2005 Dec 15. [Article]
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
  3. Camporeale G, Giordano E, Rendina R, Zempleni J, Eissenberg JC: Drosophila melanogaster holocarboxylase synthetase is a chromosomal protein required for normal histone biotinylation, gene transcription patterns, lifespan, and heat tolerance. J Nutr. 2006 Nov;136(11):2735-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Methylcrotonoyl-coa carboxylase activity
Specific Function
Carboxyltransferase subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isova...
Gene Name
MCCC2
Uniprot ID
Q9HCC0
Uniprot Name
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial
Molecular Weight
61332.65 Da
References
  1. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [Article]
  2. de Queiroz MS, Waldrop GL: Modeling and numerical simulation of biotin carboxylase kinetics: implications for half-sites reactivity. J Theor Biol. 2007 May 7;246(1):167-75. Epub 2006 Dec 28. [Article]
  3. Ludke A, Kramer R, Burkovski A, Schluesener D, Poetsch A: A proteomic study of Corynebacterium glutamicum AAA+ protease FtsH. BMC Microbiol. 2007 Jan 25;7:6. [Article]
  4. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [Article]
  5. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Metal ion binding
Specific Function
Catalyzes the ATP-dependent carboxylation of acetyl-CoA to malonyl-CoA. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase. Involved in inhibit...
Gene Name
ACACB
Uniprot ID
O00763
Uniprot Name
Acetyl-CoA carboxylase 2
Molecular Weight
276538.575 Da
References
  1. Liu Y, Zalameda L, Kim KW, Wang M, McCarter JD: Discovery of acetyl-coenzyme A carboxylase 2 inhibitors: comparison of a fluorescence intensity-based phosphate assay and a fluorescence polarization-based ADP Assay for high-throughput screening. Assay Drug Dev Technol. 2007 Apr;5(2):225-35. [Article]
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Methylcrotonoyl-coa carboxylase activity
Specific Function
Biotin-attachment subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isovale...
Gene Name
MCCC1
Uniprot ID
Q96RQ3
Uniprot Name
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial
Molecular Weight
80472.45 Da
References
  1. Friebel D, von der Hagen M, Baumgartner ER, Fowler B, Hahn G, Feyh P, Heubner G, Baumgartner MR, Hoffmann GF: The first case of 3-methylcrotonyl-CoA carboxylase (MCC) deficiency responsive to biotin. Neuropediatrics. 2006 Apr;37(2):72-8. [Article]
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Pyruvate carboxylase activity
Specific Function
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in...
Gene Name
PC
Uniprot ID
P11498
Uniprot Name
Pyruvate carboxylase, mitochondrial
Molecular Weight
129632.565 Da
References
  1. Liu L, Li Y, Zhu Y, Du G, Chen J: Redistribution of carbon flux in Torulopsis glabrata by altering vitamin and calcium level. Metab Eng. 2007 Jan;9(1):21-9. Epub 2006 Aug 12. [Article]
  2. Ferreira G, Weiss WP: Effect of biotin on activity and gene expression of biotin-dependent carboxylases in the liver of dairy cows. J Dairy Sci. 2007 Mar;90(3):1460-6. [Article]
  3. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [Article]
  4. Jitrapakdee S, Adina-Zada A, Besant PG, Surinya KH, Cleland WW, Wallace JC, Attwood PV: Differential regulation of the yeast isozymes of pyruvate carboxylase and the locus of action of acetyl CoA. Int J Biochem Cell Biol. 2007;39(6):1211-23. Epub 2007 Mar 30. [Article]
  5. Ozimek PZ, Klompmaker SH, Visser N, Veenhuis M, van der Klei IJ: The transcarboxylase domain of pyruvate carboxylase is essential for assembly of the peroxisomal flavoenzyme alcohol oxidase. FEMS Yeast Res. 2007 Oct;7(7):1082-92. Epub 2007 Feb 20. [Article]
  6. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Propionyl-coa carboxylase activity
Specific Function
Not Available
Gene Name
PCCA
Uniprot ID
P05165
Uniprot Name
Propionyl-CoA carboxylase alpha chain, mitochondrial
Molecular Weight
80058.295 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Clavero S, Martinez MA, Perez B, Perez-Cerda C, Ugarte M, Desviat LR: Functional characterization of PCCA mutations causing propionic acidemia. Biochim Biophys Acta. 2002 Nov 20;1588(2):119-25. [Article]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [Article]
  5. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [Article]
  6. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Metal ion binding
Specific Function
Catalyzes the rate-limiting reaction in the biogenesis of long-chain fatty acids. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name
ACACA
Uniprot ID
Q13085
Uniprot Name
Acetyl-CoA carboxylase 1
Molecular Weight
265551.725 Da
References
  1. Bilder P, Lightle S, Bainbridge G, Ohren J, Finzel B, Sun F, Holley S, Al-Kassim L, Spessard C, Melnick M, Newcomer M, Waldrop GL: The structure of the carboxyltransferase component of acetyl-coA carboxylase reveals a zinc-binding motif unique to the bacterial enzyme. Biochemistry. 2006 Feb 14;45(6):1712-22. [Article]
  2. Brownsey RW, Boone AN, Elliott JE, Kulpa JE, Lee WM: Regulation of acetyl-CoA carboxylase. Biochem Soc Trans. 2006 Apr;34(Pt 2):223-7. [Article]
  3. Aoki H, Kimura K, Igarashi K, Takenaka A: Soy protein suppresses gene expression of acetyl-coA carboxylase alpha from promoter PI in rat liver. Biosci Biotechnol Biochem. 2006 Apr;70(4):843-9. [Article]
  4. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [Article]
  5. Leonard E, Lim KH, Saw PN, Koffas MA: Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol. 2007 Jun;73(12):3877-86. Epub 2007 Apr 27. [Article]
  6. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Rodriguez-Melendez R, Griffin JB, Zempleni J: Biotin supplementation increases expression of the cytochrome P450 1B1 gene in Jurkat cells, increasing the occurrence of single-stranded DNA breaks. J Nutr. 2004 Sep;134(9):2222-8. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-dependent multivitamin transmembrane transporter activity
Specific Function
Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name
SLC5A6
Uniprot ID
Q9Y289
Uniprot Name
Sodium-dependent multivitamin transporter
Molecular Weight
68641.27 Da
References
  1. Grafe F, Wohlrab W, Neubert RH, Brandsch M: Transport of biotin in human keratinocytes. J Invest Dermatol. 2003 Mar;120(3):428-33. doi: 10.1046/j.1523-1747.2003.12058.x. [Article]
  2. Camporeale G, Zempleni J, Eissenberg JC: Susceptibility to heat stress and aberrant gene expression patterns in holocarboxylase synthetase-deficient Drosophila melanogaster are caused by decreased biotinylation of histones, not of carboxylases. J Nutr. 2007 Apr;137(4):885-9. [Article]
  3. Reidling JC, Said HM: Regulation of the human biotin transporter hSMVT promoter by KLF-4 and AP-2: confirmation of promoter activity in vivo. Am J Physiol Cell Physiol. 2007 Apr;292(4):C1305-12. Epub 2006 Nov 29. [Article]
  4. Janoria KG, Hariharan S, Paturi D, Pal D, Mitra AK: Biotin uptake by rabbit corneal epithelial cells: role of sodium-dependent multivitamin transporter (SMVT). Curr Eye Res. 2006 Oct;31(10):797-809. [Article]
  5. Luo S, Kansara VS, Zhu X, Mandava NK, Pal D, Mitra AK: Functional characterization of sodium-dependent multivitamin transporter in MDCK-MDR1 cells and its utilization as a target for drug delivery. Mol Pharm. 2006 May-Jun;3(3):329-39. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactat...
Gene Name
SLC5A8
Uniprot ID
Q8N695
Uniprot Name
Sodium-coupled monocarboxylate transporter 1
Molecular Weight
66577.005 Da
References
  1. Daberkow RL, White BR, Cederberg RA, Griffin JB, Zempleni J: Monocarboxylate transporter 1 mediates biotin uptake in human peripheral blood mononuclear cells. J Nutr. 2003 Sep;133(9):2703-6. doi: 10.1093/jn/133.9.2703. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55