2-Oxobutanoic Acid

Identification

Name
2-Oxobutanoic Acid
Accession Number
DB04553  (EXPT00126)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 3723 / NSC-60533
Categories
Not Available
UNII
B92RB6HY1A
CAS number
600-18-0
Weight
Average: 102.0886
Monoisotopic: 102.031694058
Chemical Formula
C4H6O3
InChI Key
TYEYBOSBBBHJIV-UHFFFAOYSA-N
InChI
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
IUPAC Name
2-oxobutanoic acid
SMILES
CCC(=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U1-aminocyclopropane-1-carboxylate deaminaseNot AvailablePseudomonas sp. (strain ACP)
UMethylmalonyl-CoA carboxyltransferase 5S subunitNot AvailablePropionibacterium freudenreichii subsp. shermanii
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
Cystathionine Beta-Synthase DeficiencyDisease
3-Phosphoglycerate dehydrogenase deficiencyDisease
Propanoate MetabolismMetabolic
Malonic AciduriaDisease
Threonine and 2-Oxobutanoate DegradationMetabolic
Hyperglycinemia, non-ketoticDisease
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDisease
Selenoamino Acid MetabolismMetabolic
Methionine MetabolismMetabolic
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDisease
Methionine Adenosyltransferase DeficiencyDisease
HypermethioninemiaDisease
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-methyltransferase DeficiencyDisease
Non Ketotic HyperglycinemiaDisease
Homocysteine DegradationMetabolic
Dimethylglycine Dehydrogenase DeficiencyDisease
Malonyl-coa decarboxylase deficiencyDisease
Glycine and Serine MetabolismMetabolic
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
Gamma-cystathionase deficiency (CTH)Disease
Homocystinuria, cystathionine beta-synthase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00005
KEGG Compound
C00109
PubChem Compound
58
PubChem Substance
46504977
ChemSpider
57
ChEBI
30831
ChEMBL
CHEMBL171246
HET
2KT
PDB Entries
1rr2 / 1tzk / 2ktn / 2kto / 2q1a / 2q1c / 2uyn / 3tdf / 4b5t / 4woq

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)33 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility79.2 mg/mLALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.62 m3·mol-1ChemAxon
Polarizability9.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9869
Blood Brain Barrier+0.9228
Caco-2 permeable-0.6181
P-glycoprotein substrateNon-substrate0.776
P-glycoprotein inhibitor INon-inhibitor0.8942
P-glycoprotein inhibitor IINon-inhibitor0.9606
Renal organic cation transporterNon-inhibitor0.9541
CYP450 2C9 substrateNon-substrate0.8362
CYP450 2D6 substrateNon-substrate0.9289
CYP450 3A4 substrateNon-substrate0.7712
CYP450 1A2 substrateNon-inhibitor0.9532
CYP450 2C9 inhibitorNon-inhibitor0.9075
CYP450 2D6 inhibitorNon-inhibitor0.9664
CYP450 2C19 inhibitorNon-inhibitor0.9475
CYP450 3A4 inhibitorNon-inhibitor0.9805
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9876
Ames testNon AMES toxic0.8311
CarcinogenicityNon-carcinogens0.5313
BiodegradationReady biodegradable0.9387
Rat acute toxicity1.6927 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9835
hERG inhibition (predictor II)Non-inhibitor0.969
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-MSsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014s-1910000000-d01bcd7b41fdcc634eea
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-9200000000-3b3816ffee5771215904
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000i-6910000000-5b264d5f7e53f3e80b12
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-6950000000-db7f6a0f03a8cce59bae
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0ftb-0920000000-a6c93d8761ef15f7f7d4
GC-MS Spectrum - EI-BGC-MSsplash10-014i-0920000000-406fe70e72dbd9c3f274
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014s-1910000000-d01bcd7b41fdcc634eea
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-9200000000-3b3816ffee5771215904
GC-MS Spectrum - GC-MSGC-MSsplash10-000i-6910000000-5b264d5f7e53f3e80b12
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-6950000000-db7f6a0f03a8cce59bae
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-8900000000-97bab6630de4df095a7f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-9200000000-0ebb2354fe3f935fe177
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0pb9-9600000000-53ebb7164f74d7d92a4d
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0zfr-5900000000-1db864754705beb79b55
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0udi-9800000000-5ba5b9ede5b1bc389b87
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-0900000000-bfdcad5bc3ed586bdede
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9i-9400000000-0061f4635858d851f127
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-9100000000-b943445194fb5f8e3a0f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-bc5920b9bd140be6b06d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-5900000000-f7dfb4554f0b9e1499c9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-9200000000-e54106ad5bf45a9f072c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-7bbba57578cf720974e3
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0900000000-bfdcad5bc3ed586bdede
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
Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Short-chain keto acid / Alpha-keto acid / Alpha-hydroxy ketone / Ketone / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-oxo monocarboxylic acid, short-chain fatty acid (CHEBI:30831) / Oxo fatty acids (C00109) / Oxo fatty acids (LMFA01060002)

Targets

Kind
Protein
Organism
Pseudomonas sp. (strain ACP)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes a cyclopropane ring-opening reaction, the irreversible conversion of 1-aminocyclopropane-1-carboxylate (ACC) to ammonia and alpha-ketobutyrate. Allows growth on ACC as a nitrogen source.
Gene Name
acdS
Uniprot ID
Q00740
Uniprot Name
1-aminocyclopropane-1-carboxylate deaminase
Molecular Weight
36671.515 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
Propionibacterium freudenreichii subsp. shermanii
Pharmacological action
Unknown
General Function
Methylmalonyl-coa carboxytransferase activity
Specific Function
The 5S subunit specifically catalyzes the transfer of the carboxyl group from biotin of the 1.3S subunit to pyruvate to form oxaloacetate and 1.3S biotin.
Gene Name
Not Available
Uniprot ID
Q70AC7
Uniprot Name
Methylmalonyl-CoA carboxyltransferase 5S subunit
Molecular Weight
55649.06 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 03:43