2-Oxo-4-Methylpentanoic Acid

Identification

Name
2-Oxo-4-Methylpentanoic Acid
Accession Number
DB03229  (EXPT00985)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
4GUJ8AH400
CAS number
Not Available
Weight
Average: 130.1418
Monoisotopic: 130.062994186
Chemical Formula
C6H10O3
InChI Key
BKAJNAXTPSGJCU-UHFFFAOYSA-N
InChI
InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
IUPAC Name
4-methyl-2-oxopentanoic acid
SMILES
CC(C)CC(=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDeacetoxycephalosporin C synthaseNot AvailableStreptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
UD-2-hydroxyisocaproate dehydrogenaseNot AvailableLactobacillus paracasei
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
  1. Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [PubMed:16805814]
External Links
Human Metabolome Database
HMDB00695
KEGG Compound
C00233
PubChem Compound
70
PubChem Substance
46506016
ChemSpider
69
BindingDB
50390988
ChEBI
48430
ChEMBL
CHEMBL445647
HET
COI
PDB Entries
1dxy / 1hjf / 1qs0 / 1umd / 2hdk / 2xjh / 2xji / 3hps / 3uzb / 3wgy
show 2 more

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.76 mg/mLALOGPS
logP0.82ALOGPS
logP1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.77 m3·mol-1ChemAxon
Polarizability13 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.981
Blood Brain Barrier+0.9523
Caco-2 permeable-0.5504
P-glycoprotein substrateNon-substrate0.7659
P-glycoprotein inhibitor INon-inhibitor0.8665
P-glycoprotein inhibitor IINon-inhibitor0.923
Renal organic cation transporterNon-inhibitor0.9552
CYP450 2C9 substrateNon-substrate0.8451
CYP450 2D6 substrateNon-substrate0.9087
CYP450 3A4 substrateNon-substrate0.6812
CYP450 1A2 substrateNon-inhibitor0.9506
CYP450 2C9 inhibitorNon-inhibitor0.9094
CYP450 2D6 inhibitorNon-inhibitor0.9578
CYP450 2C19 inhibitorNon-inhibitor0.9616
CYP450 3A4 inhibitorNon-inhibitor0.9712
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9892
Ames testNon AMES toxic0.9491
CarcinogenicityNon-carcinogens0.5126
BiodegradationReady biodegradable0.9073
Rat acute toxicity1.5348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9909
hERG inhibition (predictor II)Non-inhibitor0.9673
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) (3 TMS)GC-MSsplash10-000i-9400000000-49d055f04bfe1877ac5b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-029j-8930000000-c6c54bf6ee2995a2195b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-1910000000-0ba38257e25873312809
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a5c-4930000000-61247369a805fa2a77a7
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9510000000-8bfc5a54e29f65edf361
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-00lj-9620000000-aa8409ceb2359d903f38
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9400000000-49d055f04bfe1877ac5b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-029j-8930000000-c6c54bf6ee2995a2195b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1910000000-0ba38257e25873312809
GC-MS Spectrum - GC-MSGC-MSsplash10-0a5c-4930000000-61247369a805fa2a77a7
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9510000000-8bfc5a54e29f65edf361
GC-MS Spectrum - GC-MSGC-MSsplash10-00lj-9620000000-aa8409ceb2359d903f38
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ks-7930000000-4e9cfd715fa884d30e7f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9500000000-709ebcb57f006703c269
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-bed7ac074a60210971e3
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-014i-9200000000-2fa08d2b4df406cf63ea
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014j-9000000000-045be8e8dca3f93d45ba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-237fa8ad6bfb929be31e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004r-9700000000-8d38d24fce78b1ff13e6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a59-9000000000-759cfc0817917283d1a5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4l-9000000000-2a068ada71fbe0a5a988
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4l-9000000000-58e61e31f3c96d84d799
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-08gr-7900000000-31021fda89eb6535185f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0btm-9200000000-3bf5df4b557ef87267f4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-37839bf70647d24b94a4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4900000000-796467909d1d4c087a07
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ri-9400000000-0abcd021721f32c10e42
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-015l-9000000000-5c33a47dfeb09a182983
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-237fa8ad6bfb929be31e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004r-9700000000-8d38d24fce78b1ff13e6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a59-9000000000-759cfc0817917283d1a5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-2a068ada71fbe0a5a988
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-58e61e31f3c96d84d799
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0900000000-556a0d1cf568609752d1
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-004r-5900000000-20f6923c8ed45e9fa088
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 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:48430)

Targets

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
Lactobacillus paracasei
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function
Catalyzes the NAD dependent reversible, stereospecific interconversion between 2-ketocarboxylic acids and D-2-hydroxy-carboxylic acids.
Gene Name
Not Available
Uniprot ID
P17584
Uniprot Name
D-2-hydroxyisocaproate dehydrogenase
Molecular Weight
36892.78 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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:25