Identification
- Generic Name
- alpha-Ketoisovalerate
- DrugBank Accession Number
- DB04074
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for alpha-Ketoisovalerate (DB04074)
- Weight
- Average: 116.1152
Monoisotopic: 116.047344122 - Chemical Formula
- C5H8O3
- Synonyms
- 2-Keto-3-methylbutyric acid
- 2-Ketoisovaleric acid
- 2-Ketovaline
- 2-Oxo-3-methylbutanoic acid
- 3-Methyl-2-oxobutanoate
- 3-Methyl-2-oxobutanoic acid
- 3-Methyl-2-oxobutyric acid
- alpha-Ketovaline
- Dimethylpyruvic acid
- Isopropylglyoxylic acid
- α-keto-isovaleric acid
- α-oxo-β-methylbutyricacid
- α-oxoisovaleric acid
- External IDs
- FEMA NO. 3869, ACID-
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBranched-chain-amino-acid aminotransferase, mitochondrial Not Available Humans U3-methyl-2-oxobutanoate hydroxymethyltransferase Not Available Neisseria meningitidis serogroup B (strain MC58) UDeacetoxycephalosporin C synthase Not Available Streptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602) U2-isopropylmalate synthase Not Available Mycobacterium tuberculosis - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- 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
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Calcium alpha-Ketoisovalerate 00T4085CBX 51828-94-5 IMZGMVJQWNJKCI-UHFFFAOYSA-L
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Short-chain keto acids and derivatives
- Direct Parent
- Short-chain keto acids and derivatives
- Alternative Parents
- Methyl-branched fatty acids / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alpha-hydroxy ketone / Alpha-keto acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- 2-oxo monocarboxylic acid (CHEBI:16530) / Branched fatty acids (C00141) / Branched fatty acids (LMFA01020274)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 34P71D50E0
- CAS number
- 759-05-7
- InChI Key
- QHKABHOOEWYVLI-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
- IUPAC Name
- 3-methyl-2-oxobutanoic acid
- SMILES
- CC(C)C(=O)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000019
- KEGG Compound
- C00141
- PubChem Compound
- 49
- PubChem Substance
- 46508074
- ChemSpider
- 48
- BindingDB
- 50390989
- ChEBI
- 16530
- ChEMBL
- CHEMBL146554
- ZINC
- ZINC000001532553
- PDBe Ligand
- KIV
- Wikipedia
- Alpha-Ketoisovaleric_acid
- PDB Entries
- 1hjg / 1kta / 1o68 / 1sr9 / 3u6w / 4ov4 / 6ulz / 8jdx
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Diabetic Nephropathy 1 4 Unknown Status Treatment Muscular Atrophy 1 3 Recruiting Supportive Care Nephrotic Syndrome 1 2, 3 Not Yet Recruiting Treatment Hemodialysis Treatment / Kidney Function 1 1, 2 Completed Basic Science Renal Insufficiency,Chronic 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Drug delivery system Oral 0.105 g Tablet Oral 67.000 mg Tablet Oral 105.000 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 31.5 °C PhysProp boiling point (°C) 170.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 30.2 mg/mL ALOGPS logP 0.49 ALOGPS logP 1.31 Chemaxon logS -0.59 ALOGPS pKa (Strongest Acidic) 3.37 Chemaxon pKa (Strongest Basic) -9.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 27.19 m3·mol-1 Chemaxon Polarizability 11.04 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9764 Blood Brain Barrier + 0.9371 Caco-2 permeable - 0.6143 P-glycoprotein substrate Non-substrate 0.7906 P-glycoprotein inhibitor I Non-inhibitor 0.9239 P-glycoprotein inhibitor II Non-inhibitor 0.9466 Renal organic cation transporter Non-inhibitor 0.9548 CYP450 2C9 substrate Non-substrate 0.8246 CYP450 2D6 substrate Non-substrate 0.9285 CYP450 3A4 substrate Non-substrate 0.704 CYP450 1A2 substrate Non-inhibitor 0.9811 CYP450 2C9 inhibitor Non-inhibitor 0.9109 CYP450 2D6 inhibitor Non-inhibitor 0.9584 CYP450 2C19 inhibitor Non-inhibitor 0.9804 CYP450 3A4 inhibitor Non-inhibitor 0.9813 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9905 Ames test Non AMES toxic 0.9163 Carcinogenicity Carcinogens 0.584 Biodegradation Ready biodegradable 0.885 Rat acute toxicity 1.5628 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9939 hERG inhibition (predictor II) Non-inhibitor 0.9736
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 121.7770615 predictedDarkChem Lite v0.1.0 [M-H]- 121.7779615 predictedDarkChem Lite v0.1.0 [M-H]- 121.7928615 predictedDarkChem Lite v0.1.0 [M-H]- 123.08367 predictedDeepCCS 1.0 (2019) [M+H]+ 122.3316615 predictedDarkChem Lite v0.1.0 [M+H]+ 121.8243615 predictedDarkChem Lite v0.1.0 [M+H]+ 121.8830615 predictedDarkChem Lite v0.1.0 [M+H]+ 125.8777 predictedDeepCCS 1.0 (2019) [M+Na]+ 121.7870615 predictedDarkChem Lite v0.1.0 [M+Na]+ 121.7293615 predictedDarkChem Lite v0.1.0 [M+Na]+ 121.6819615 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.36316 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- L-valine transaminase activity
- Specific Function
- Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
- Gene Name
- BCAT2
- Uniprot ID
- O15382
- Uniprot Name
- Branched-chain-amino-acid aminotransferase, mitochondrial
- Molecular Weight
- 44287.445 Da
References
- Kind
- Protein
- Organism
- Neisseria meningitidis serogroup B (strain MC58)
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the reversible reaction in which hydroxymethyl group from 5,10-methylenetetrahydrofolate is tranferred onto alpha-ketoisovalerate to form ketopantoate.
- Gene Name
- panB
- Uniprot ID
- Q9JZW6
- Uniprot Name
- 3-methyl-2-oxobutanoate hydroxymethyltransferase
- Molecular Weight
- 27739.07 Da
References
- Kind
- Protein
- Organism
- Streptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
- Pharmacological action
- Unknown
- General Function
- L-ascorbic acid binding
- Specific Function
- Catalyzes the step from penicillin N to deacetoxy-cephalosporin C.
- Gene Name
- cefE
- Uniprot ID
- P18548
- Uniprot Name
- Deacetoxycephalosporin C synthase
- Molecular Weight
- 34555.38 Da
References
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Catalyzes the condensation of the acetyl group of acetyl-CoA with 3-methyl-2-oxobutanoate (2-oxoisovalerate) to form 3-carboxy-3-hydroxy-4-methylpentanoate (2-isopropylmalate).
- Specific Function
- 2-isopropylmalate synthase activity
- Gene Name
- leuA
- Uniprot ID
- P9WQB3
- Uniprot Name
- 2-isopropylmalate synthase
- Molecular Weight
- 70112.945 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
- Gene Name
- SLC16A7
- Uniprot ID
- O60669
- Uniprot Name
- Monocarboxylate transporter 2
- Molecular Weight
- 52199.745 Da
References
- Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
- Gene Name
- SLC16A1
- Uniprot ID
- P53985
- Uniprot Name
- Monocarboxylate transporter 1
- Molecular Weight
- 53943.685 Da
References
- Broer S, Schneider HP, Broer A, Rahman B, Hamprecht B, Deitmer JW: Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH. Biochem J. 1998 Jul 1;333 ( Pt 1):167-74. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Symporter activity
- Specific Function
- Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine...
- Gene Name
- SLC16A3
- Uniprot ID
- O15427
- Uniprot Name
- Monocarboxylate transporter 4
- Molecular Weight
- 49468.9 Da
References
- Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 16, 2020 21:12