NAV

2-Amino-3-Ketobutyric Acid

Identification

Generic Name
2-Amino-3-Ketobutyric Acid
DrugBank Accession Number
DB03915
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 117.1033
Monoisotopic: 117.042593095
Chemical Formula
C4H7NO3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U2-amino-3-ketobutyrate coenzyme A ligaseNot AvailableEscherichia coli (strain K12)
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
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Toxicity

Not Available

Pathways
PathwayCategory
Glycine and Serine MetabolismMetabolic
Non-Ketotic HyperglycinemiaDisease
SarcosinemiaDisease
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Hyperglycinemia, Non-KetoticDisease
3-Phosphoglycerate Dehydrogenase DeficiencyDisease
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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Short-chain keto acids and derivatives / Beta-keto acids and derivatives / Beta-hydroxy ketones / 1,3-dicarbonyl compounds / Alpha-amino ketones / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
1,3-dicarbonyl compound / Aliphatic acyclic compound / Alpha-aminoketone / Amine / Amino acid / Beta-hydroxy ketone / Beta-keto acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, 2-amino-3-oxobutanoic acid (CHEBI:40673) / Oxo fatty acids (C03508) / Oxo fatty acids (LMFA01060172)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SAUCHDKDCUROAO-VKHMYHEASA-N
InChI
InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-3-oxobutanoic acid
SMILES
CC(=O)[C@H](N)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0006454
KEGG Compound
C03508
PubChem Compound
440033
PubChem Substance
46508458
ChemSpider
389046
ChEBI
40673
ZINC
ZINC000000901672
PDBe Ligand
AKB
PDB Entries
1fc4 / 5y1g

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility206.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.1Chemaxon
logS0.25ALOGPS
pKa (Strongest Acidic)1.87Chemaxon
pKa (Strongest Basic)7.25Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area80.39 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity25.53 m3·mol-1Chemaxon
Polarizability10.47 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9437
Blood Brain Barrier+0.5727
Caco-2 permeable-0.9077
P-glycoprotein substrateNon-substrate0.7854
P-glycoprotein inhibitor INon-inhibitor0.9775
P-glycoprotein inhibitor IINon-inhibitor0.9866
Renal organic cation transporterNon-inhibitor0.9639
CYP450 2C9 substrateNon-substrate0.8457
CYP450 2D6 substrateNon-substrate0.8871
CYP450 3A4 substrateNon-substrate0.8134
CYP450 1A2 substrateNon-inhibitor0.9594
CYP450 2C9 inhibitorNon-inhibitor0.9629
CYP450 2D6 inhibitorNon-inhibitor0.9559
CYP450 2C19 inhibitorNon-inhibitor0.9567
CYP450 3A4 inhibitorNon-inhibitor0.9233
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9947
Ames testNon AMES toxic0.9461
CarcinogenicityNon-carcinogens0.6473
BiodegradationReady biodegradable0.83
Rat acute toxicity1.4522 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9882
hERG inhibition (predictor II)Non-inhibitor0.9859
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-006x-9000000000-22150e9e4fa3d3433203
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-17544f674427d4ee887e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-4900000000-810d11d248b6b492afcc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fu-9000000000-bd975ca187c5dcfd02d6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9100000000-fad6990c9191a5097359
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-bb71edab6432830b7743
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fb9-9000000000-7223f30625ad679c25d7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-120.3336969
predicted
DarkChem Lite v0.1.0
[M-H]-116.7027
predicted
DeepCCS 1.0 (2019)
[M+H]+121.2356969
predicted
DarkChem Lite v0.1.0
[M+H]+120.396996
predicted
DeepCCS 1.0 (2019)
[M+Na]+120.4824969
predicted
DarkChem Lite v0.1.0
[M+Na]+129.07033
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-amino-3-ketobutyrate coenzyme A ligase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the cleavage of 2-amino-3-ketobutyrate to glycine and acetyl-CoA.
Gene Name
kbl
Uniprot ID
P0AB77
Uniprot Name
2-amino-3-ketobutyrate coenzyme A ligase
Molecular Weight
43116.625 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52