Ubidecarenone

Identification

Summary

Ubidecarenone is a cofactor found in various dietary supplements.

Generic Name

Ubidecarenone

DrugBank Accession Number

DB09270

Background

Ubidecarenone, also called coenzyme Q10, is a 1,4-benzoquinone. From its name (Q10), the Q refers to the constitutive quinone group, and 10 is related to the number of isoprenyl subunits in its tail.¹ It is a powerful antioxidant, a lipid-soluble and essential cofactor in mitochondrial oxidative phosphorylation.² The ubidecarenone is the coenzyme destined for mitochondrial enzyme complexes involved in oxidative phosphorylation in the production of ATP. It is fundamental for cells that have a high metabolic demand.⁷ Ubidecarenone is sold as a dietary supplement and is not FDA approved as a drug - it is not meant to treat, cure or prevent any disease. FDA does not approve this dietary supplements before sold nor regulate the manufacturing process.⁸

Type

Small Molecule

Groups

Approved, Investigational, Nutraceutical

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Ubidecarenone (DB09270)

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Weight

Average: 863.3435
Monoisotopic: 862.683911368

Chemical Formula

C₅₉H₉₀O₄

Synonyms

• Coenzyme Q-10
• Coenzyme Q10
• CoQ10
• Ubidecarenone
• Ubiquinone
• Vitamin Q10

External IDs

• API 31510
• API-31510
• NSC-140865

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Pharmacology

Indication

The diet supplements containing ubidecarenone are indicated, as stated in the product label, to assist individuals with cardiovascular complaints including congestive heart failure and systolic hypertension. In the product, ubidecarenone is used to increase the cardiac input as well as for the prevention of several other diseases like Parkinson, fibromyalgia, migraine, periodontal disease and diabetes, based on preclinical studies.⁹ It is important to highlight that these products are not FDA approved and it is recommended to use under discretion.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Prophylaxis of	Migraine		••• •••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Ubidecarenon has roles in many prysiological process including sulfide oxidation, regulation of mitochondrial permeability transition pore and translocation of protons and calcium ions accross biological membranes. Studies have shown its benefitial effect in treating cancer, statin myopathy, congestive heart failure and hypertension.²

Mechanism of action

Ubidecarenone is an essential cofactor in the mitochondrial electron transport chain. Its functions are the acceptance of electrons from the complex I and II and this activity is vital for the production of ATP. It acts as a mobile redox agent shuttling electrons and protons in the electron transport chain.⁵ Ubidecarenone also presents antioxidant activity in mitochondria and cellular membranes, protecting against peroxidation of lipid membranes as well as inhibiting oxidation of LDL-cholesterol.¹⁰

Target	Actions	Organism
ANADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrial	cofactor	Humans
ASuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	cofactor	Humans

Absorption

Ubidecarenone is absorbed from the small intestine into the lymphatics and then it can enter the blood. The hydrophobicity and large molecular weight limit its absorption making it very poor and variable depending on the food intake and the number of lipids presented in the food. The absorption is lower in the presence of an empty stomach and greater in presence of high lipid food diet. The daily dosage of ubidecarenone presents the reach of maximal serum concentration by reaching a plateau after three weeks.¹⁰ The pharmacokinetic properties may vary between different brands but studies have reported an AUC of 11.51 mcg h/ml and a Cmax of 0.32 mcg/ml at a time of 7.9 h.³

Volume of distribution

Ubidecarenone is distributed to the various tissues of the body and it is able to enter the brain.¹⁰ In preclinical studies with intravenous administration of ubidecarenone, it is reported a volume of distribution of 20.4 L/kg which reflects its ability to penetrate extensively into organs and tissues.⁴ AS a general rule, tissues with high-energy requirements or metabolic activity tend to presents higher amounts of ubidecarenone, these organs can be heart, kidney, liver and muscle.⁵

Protein binding

In the blood, ubidecarenone is split into the various lipoprotein particles including LDL and VLDL.¹⁰ The plasma concentration of ubidecarenone is highly dependent on the presence of plasma lipoproteins and about 95% of the administered form is found in the reduced form.⁵

Metabolism

Studies indicate that there is no saturation process during the metabolism of ubidecarenone. It is metabolized in all tissues by the phosphorylation in the cells and transportation to the kidneys for further excretion by the urine.¹¹ After exerting its action, ubidecarenone is reduced and forms hydroquinone which is capable of recycling and regenerates other antioxidants such as tocopherol and ascorbate. The later metabolism of hydroquinone generates the formation of Q acid I and Q acid II in free and conjugated forms.⁵

Route of elimination

The main elimination route of ubidecarenone is through the bile. After its oral administration, over 60% of the dose is excreted in the feces in the form of unchanged ubidecarenone and a small fraction of the metabolites.^10,5 In the urine, ubidecarenone is bound to saposin B protein and represents only 8.3% of the total administered dose.⁵

Half-life

The pharmacokinetic properties may vary between different brands but studies have reported a half-life of ubidecarenone of 21.7 h.³

Clearance

In preclinical studies with intravenous administration of ubidecarenone, it is reported a total clearance of 1.18 ml h/kg which was indicative of a prolonged elimination.⁴

Adverse Effects

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Toxicity

There have not been reports of adverse events of diet supplementation with ubidecarenone.⁶ The normal side effects reported in humans are related to the gastrointestinal tract.⁵

Pathways

Not Available

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Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acarbose	The risk or severity of hypoglycemia can be increased when Ubidecarenone is combined with Acarbose.
Acenocoumarol	The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Ubidecarenone.
Acetohexamide	The risk or severity of hypoglycemia can be increased when Ubidecarenone is combined with Acetohexamide.
Acipimox	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Acipimox is combined with Ubidecarenone.
Albiglutide	The risk or severity of hypoglycemia can be increased when Ubidecarenone is combined with Albiglutide.

Food Interactions

• Take with or without food. Many different products contain ubidecarenone; refer to the product monograph for more specific instructions.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Coenzyme q10, (2z)-	U705VLF0VW	65085-29-2	ACTIUHUUMQJHFO-LLOLQPSSSA-N

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Acti-ubiquinone 50 Cap 50mg	Capsule	50 mg / cap	Oral	Acti Form Ltd.	1991-12-31	2005-03-21
Biogard Ubiquinone Cap 30mg	Capsule	30 mg	Oral	Sisu Inc.	1994-12-31	2001-08-01
Biomed Co Q 10	Capsule	100 mg / cap	Oral	Sisu Inc.	1998-02-11	2008-07-25
Cell Tech Coenzyme Q10 - Cap 30mg	Capsule	30 mg / cap	Oral	Cell Tech	1996-11-12	2000-10-05
Cellsparc 360	Capsule	60 mg / cap	Oral	Aim International, Inc.	1998-07-29	2008-09-03

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
B.E.T. Complex	Ubidecarenone (10 mg) + Beta carotene (1250 unit) + Calcium ascorbate (75 mg) + Chromium (400 mcg) + Cyanocobalamin (100 mcg) + Folic acid (0.2 mg) + Iodine (0.15 mg) + Magnesium (200 mg) + Manganese (5 mg) + Nicotinamide (35 mg) + Sodium metavanadate (75 mcg) + Vitamin A palmitate (1250 unit) + alpha-Tocopherol succinate (50 unit)	Tablet	Oral	Abundance Naturally Ltd	2000-12-06	2004-06-30
Biosculpt	Ubidecarenone (1.5 mg / 30 mL) + Choline bitartrate (0.3 mg / 30 mL) + Chromium (40 mcg / 30 mL) + Inositol (0.3 mg / 30 mL) + Calcium pantothenate (60 mg / 30 mL) + Pyridoxine hydrochloride (4 mg / 30 mL)	Solution	Oral	Maxion Nutrition Corp.	2002-06-10	2004-07-20
C.V. Formula	Ubidecarenone (30 mg / mL) + Vitamin E (30 unit / mL)	Liquid	Oral	Morinda Canada	2001-06-27	2005-07-13
Co-q10 and Vitamin E	Ubidecarenone (100 mg) + alpha-Tocopherol succinate (300 unit)	Capsule	Oral	Biomed International Products Corp.	2003-10-01	2006-06-29
Co-q10 M.R.B. 100mg and Vitamin E	Ubidecarenone (100 mg) + Vitamin E (150 unit)	Capsule	Oral	Inno Vite Incorporated	2004-01-23	2007-07-31

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dyzbac	Ubidecarenone (25 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (500 [iU]/1) + Leucovorin (1 mg/1) + Lipoic acid (150 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1)	Tablet	Oral	Basiem	2015-11-05	2016-01-01
Dyzbac	Ubidecarenone (50 mg/1) + Ascorbic acid (150 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Lipoic acid (125 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1)	Tablet	Oral	Basiem	2015-10-28	2015-11-01
IQQU Acne Serum	Ubidecarenone (0.0012 g/1g) + Lecithin, soybean (0.024 g/30g) + Levocarnitine (0.012 g/1g)	Lotion	Topical	Iqqu Usa Co.	2009-08-01	Not applicable
Lexazin	Coenzyme q10, (2z)- (50 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (500 [iU]/1) + Folic acid (1 mg/1) + Mecobalamin (5 mg/1) + NADH (5 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Thiamine hydrochloride (25 mg/1)	Capsule	Oral	Sterling Knight Pharmaceuticals LLC	2018-01-02	2018-10-01
Mebolex	Ubidecarenone (25 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Lipoic acid (150 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1)	Tablet	Oral	Solubiomix	2015-10-28	2016-01-01

Categories

ATC Codes

C01EB09 — Ubidecarenone

• C01EB — Other cardiac preparations
• C01E — OTHER CARDIAC PREPARATIONS
• C01 — CARDIAC THERAPY
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• Agents Causing Muscle Toxicity
• Benzoquinones
• Cardiac Therapy
• Coenzymes
• Diet, Food, and Nutrition
• Electron Transport Chain Complex Proteins
• Enzymes and Coenzymes
• Food
• Hypoglycemia-Associated Agents
• Micronutrients
• Other Nutritional Agents
• P-glycoprotein substrates
• Physiological Phenomena
• Quinones
• Ubiquinone
• Vitamins

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinones

Alternative Parents

Polyterpenoids / Polyprenylbenzoquinones / P-benzoquinones / Vinylogous esters / Organic oxides / Hydrocarbon derivatives

Substituents

Aliphatic homomonocyclic compound / Carbonyl group / Cyclic ketone / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound / Organooxygen compound / P-benzoquinone / Polyprenylbenzoquinone

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ubiquinones (CHEBI:46245) / ubiquinones, Coenzymes (C11378) / Ubiquinones (LMPR02010001)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

EJ27X76M46

CAS number

303-98-0

InChI Key

ACTIUHUUMQJHFO-UPTCCGCDSA-N

InChI

InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+

IUPAC Name

2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

SMILES

COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O

References

General References

1. Ernster L, Dallner G: Biochemical, physiological and medical aspects of ubiquinone function. Biochim Biophys Acta. 1995 May 24;1271(1):195-204. [Article]
2. Xue R, Yang J, Wu J, Meng Q, Hao J: Coenzyme Q10 inhibits the activation of pancreatic stellate cells through PI3K/AKT/mTOR signaling pathway. Oncotarget. 2017 Sep 23;8(54):92300-92311. doi: 10.18632/oncotarget.21247. eCollection 2017 Nov 3. [Article]
3. Kang EY, Choi JW, Gwak HS, Chun IK: Comparison of bioavailability of two ubidecarenone products in healthy Korean volunteers. Int J Clin Pharmacol Ther. 2009 Mar;47(3):207-14. [Article]
4. Kalenikova EI, Gorodetskaya EA, Medvedev OS: Pharmacokinetics of coenzyme q10. Bull Exp Biol Med. 2008 Sep;146(3):313-6. [Article]
5. Bhagavan HN, Chopra RK: Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics. Free Radic Res. 2006 May;40(5):445-53. doi: 10.1080/10715760600617843. [Article]
6. Shults CW, Oakes D, Kieburtz K, Beal MF, Haas R, Plumb S, Juncos JL, Nutt J, Shoulson I, Carter J, Kompoliti K, Perlmutter JS, Reich S, Stern M, Watts RL, Kurlan R, Molho E, Harrison M, Lew M: Effects of coenzyme Q10 in early Parkinson disease: evidence of slowing of the functional decline. Arch Neurol. 2002 Oct;59(10):1541-50. [Article]
7. FDA Reports [Link]
8. Pubmedhealth [Link]
9. Diet supplement label [Link]
10. Coenzyme Q [Link]
11. Journal of Health Science [Link]

External Links

Human Metabolome Database

HMDB0001072

KEGG Drug

D01065

KEGG Compound

C11378

PubChem Compound

5281915

PubChem Substance

310265165

ChemSpider

4445197

RxNav

21406

ChEBI

46245

ChEMBL

CHEMBL454801

ZINC

ZINC000085427689

PDBe Ligand

U10

Wikipedia

Coenzyme_Q10

PDB Entries

1aig / 1aij / 1bcc / 1ds8 / 1dv3 / 1dv6 / 1e14 / 1e6d / 1f6n / 1fnp …

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MSDS

Download (92.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Coenzyme Q10	1
4	Completed	Treatment	Dilated Cardiomyopathy (DCM)	1
4	Completed	Treatment	Hemodialysis Treatment / Renal Failure, Chronic Renal Failure	1
4	Completed	Treatment	Muscle Weakness / Myalgia / Side Effects of Statins	1
4	Recruiting	Treatment	Chronic Kidney Disease (CKD)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule	Oral	50 mg / cap
Capsule	Oral	150 mg
Capsule	Oral	50 mg
Capsule	Oral	30 mg
Capsule	Oral	100 mg / cap
Solution	Oral
Liquid	Oral
Capsule	Oral	30 mg / cap
Capsule	Oral	30 mg / mg
Tablet	Oral	10 mg / tab
Capsule	Oral	50.0 mg
Capsule	Oral	60 mg / cap
Powder, for suspension	Oral
Capsule	Oral	12 mg
Capsule, liquid filled	Oral	100 mg/1
Capsule	Oral	10 mg
Capsule	Oral	100 mg
Tablet	Oral	100 mg
Capsule	Oral	60 mg
Capsule	Oral	80 mg
Capsule	Oral	15 mg
Powder	Oral
Capsule	Oral	10 mg / cap
Capsule	Oral	200 mg/1
Tablet, coated	Oral
Tablet, coated	Oral	10 mg
Tablet	Oral	10 MG
Tablet	Oral
Lotion	Topical
Solution	Oral
Capsule	Oral
Pill
Capsule	Oral	20 mg
Capsule, liquid filled	Oral
Capsule, liquid filled	Oral
Tablet	Oral
Capsule	Oral	15 mg / cap
Capsule
Tablet	Oral	60 mg
Capsule	Oral	25 mg / cap
Capsule, coated	Oral
Solution	Oral	50 MG/10ML
Capsule	Oral	20 mg / cap
Capsule	Oral
Capsule, gelatin coated	Oral
Tablet, sugar coated	Oral	10 mg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	50-52ºC	MSDS
water solubility	Sparingly soluble	MSDS
logP	10	Lucangioli S. and Tripodi V., Der Pharmacia Sinica, (2012), 3 (4):406-407

Predicted Properties

Property	Value	Source
Water Solubility	0.000193 mg/mL	ALOGPS
logP	9.94	ALOGPS
logP	17.16	Chemaxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-4.7	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	52.6 Å2	Chemaxon
Rotatable Bond Count	31	Chemaxon
Refractivity	286.61 m3·mol-1	Chemaxon
Polarizability	112.37 Å3	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052r-2102202940-6be2473fdabfb060e89b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0000000090-832cd33e82accbccf9f8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-02c2-6339853120-6961fb4cd77055f72267
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-02vj-0310010190-6101902ec40cc865f92f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-08i3-1054911010-e2ac59b7e541faccb153
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0594140680-3d49aad2874937d25f4c

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	364.4592444	predicted	DarkChem Lite v0.1.0
[M-H]-	330.6725444	predicted	DarkChem Lite v0.1.0
[M-H]-	366.5449444	predicted	DarkChem Lite v0.1.0
[M-H]-	322.55243	predicted	DeepCCS 1.0 (2019)
[M+H]+	365.0836444	predicted	DarkChem Lite v0.1.0
[M+H]+	366.2099444	predicted	DarkChem Lite v0.1.0
[M+H]+	324.44785	predicted	DeepCCS 1.0 (2019)
[M+Na]+	365.1877444	predicted	DarkChem Lite v0.1.0
[M+Na]+	365.1860444	predicted	DarkChem Lite v0.1.0
[M+Na]+	330.23193	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. NADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrial

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Cofactor

General Function

Poly(a) rna binding

Specific Function

Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons ...

Gene Name

NDUFV3

Uniprot ID

P56181

Uniprot Name

NADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrial

Molecular Weight

11940.435 Da

References

1. Bhagavan HN, Chopra RK: Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics. Free Radic Res. 2006 May;40(5):445-53. doi: 10.1080/10715760600617843. [Article]

Details2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Cofactor

General Function

Succinate dehydrogenase activity

Specific Function

Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate ...

Gene Name

SDHA

Uniprot ID

P31040

Uniprot Name

Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

Molecular Weight

72690.975 Da

References

1. Bhagavan HN, Chopra RK: Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics. Free Radic Res. 2006 May;40(5):445-53. doi: 10.1080/10715760600617843. [Article]

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Drug created at October 28, 2015 15:41 / Updated at February 20, 2024 23:55