Identification

Name
Alpha-ketoisovalerate
Accession Number
DB04074  (EXPT01974)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2-Keto-3-methylbutyric acid
  • 2-Ketovaline
  • 2-Oxo-3-methylbutanoate
  • 2-Oxoisopentanoate
  • 2-Oxoisovalerate
  • 3-Methyl-2-oxobutanoate
  • 3-Methyl-2-oxobutanoic acid
  • 3-Methyl-2-oxobutyric acid
  • alpha-Ketovaline
External IDs
FEMA NO. 3869, ACID-
Categories
UNII
34P71D50E0
CAS number
759-05-7
Weight
Average: 116.1152
Monoisotopic: 116.047344122
Chemical Formula
C5H8O3
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBranched-chain-amino-acid aminotransferase, mitochondrialNot AvailableHuman
U3-methyl-2-oxobutanoate hydroxymethyltransferaseNot AvailableNeisseria meningitidis serogroup B (strain MC58)
UDeacetoxycephalosporin C synthaseNot AvailableStreptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
U2-isopropylmalate synthaseNot AvailableMycobacterium 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
Valine, Leucine and Isoleucine DegradationMetabolic
Beta-Ketothiolase DeficiencyDisease
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
3-hydroxyisobutyric aciduriaDisease
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDisease
3-Methylglutaconic Aciduria Type IDisease
3-Methylglutaconic Aciduria Type IVDisease
Maple Syrup Urine DiseaseDisease
Propionic AcidemiaDisease
3-Methylglutaconic Aciduria Type IIIDisease
Methylmalonic AciduriaDisease
Isovaleric AciduriaDisease
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDisease
Isobutyryl-coa dehydrogenase deficiencyDisease
Isovaleric acidemiaDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00019
KEGG Compound
C00141
PubChem Compound
49
PubChem Substance
46508074
ChemSpider
48
BindingDB
50390989
ChEBI
16530
ChEMBL
CHEMBL146554
HET
KIV
PDB Entries
1hjg / 1kta / 1o68 / 1sr9 / 3u6w / 4ov4

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)31.5 °CPhysProp
boiling point (°C)170.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility30.2 mg/mLALOGPS
logP0.49ALOGPS
logP1.31ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity27.19 m3·mol-1ChemAxon
Polarizability11.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9764
Blood Brain Barrier+0.9371
Caco-2 permeable-0.6143
P-glycoprotein substrateNon-substrate0.7906
P-glycoprotein inhibitor INon-inhibitor0.9239
P-glycoprotein inhibitor IINon-inhibitor0.9466
Renal organic cation transporterNon-inhibitor0.9548
CYP450 2C9 substrateNon-substrate0.8246
CYP450 2D6 substrateNon-substrate0.9285
CYP450 3A4 substrateNon-substrate0.704
CYP450 1A2 substrateNon-inhibitor0.9811
CYP450 2C9 inhibitorNon-inhibitor0.9109
CYP450 2D6 inhibitorNon-inhibitor0.9584
CYP450 2C19 inhibitorNon-inhibitor0.9804
CYP450 3A4 inhibitorNon-inhibitor0.9813
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9905
Ames testNon AMES toxic0.9163
CarcinogenicityCarcinogens 0.584
BiodegradationReady biodegradable0.885
Rat acute toxicity1.5628 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.9736
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000i-9500000000-ff936b879a69b5d118f8
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000i-8920000000-e37b37d64d43dcf763f0
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9400000000-e3995acc4818a98d0f48
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-0f79-9720000000-5d89487273e44ea61a68
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9700000000-209c737dcac7df2b198c
GC-MS Spectrum - EI-BGC-MSsplash10-0f79-5920000000-759a2f01b4f52767ade2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9500000000-ff936b879a69b5d118f8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-8920000000-e37b37d64d43dcf763f0
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9400000000-e3995acc4818a98d0f48
GC-MS Spectrum - GC-MSGC-MSsplash10-0f79-9720000000-5d89487273e44ea61a68
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-7900000000-7e325567183fb56996d5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0ufr-0930000000-be90b06add7135b4a539
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-10ab58a33e9ca7dbace0
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-ad51ff01c94b6046ad64
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-9993174a7b1801b90ddb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00xr-9500000000-293818b81e0879b6feb2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-9000000000-75058f27a2178b9cf121
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-4c20af39e8ee009d5278
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r2-9400000000-21f8c3fae79161c82099
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-9000000000-5f25e41413738bb6b5d7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-801af00dea93fcfd637d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-8900000000-5185c7dfc72c25069904
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-9200000000-7e2a275a65197f96f5d7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0600-9000000000-0013e0ff06f9896a1337
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-9993174a7b1801b90ddb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00xr-9500000000-1a58c6a6b4f5477dabdd
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-75058f27a2178b9cf121
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-cc4465a47e663be66df5
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-00di-9100000000-19511890852fce513a02
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Branched fatty acid / Methyl-branched fatty acid / Short-chain keto acid / Alpha-keto acid / Fatty acyl / Alpha-hydroxy ketone / Ketone / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-oxo monocarboxylic acid (CHEBI:16530) / Branched fatty acids (C00141) / Branched fatty acids (LMFA01020274)

Targets

Kind
Protein
Organism
Human
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10417314]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:9639576]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11101640]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:30