ChemFOnt: Showing chemical card for L-2-Amino-3-oxobutanoic acid (CFc000002745)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:42 UTC

Chemfont ID

CFc000002745

Molecule Identification

Common Name

L-2-Amino-3-oxobutanoic acid

Definition

L-2-Amino-3-oxobutanoic acid or L-2-amino acetic acid is involved in glycine/serine metabolism and is a breakdown product from glycine. It spontaneously decomposes to aminoacetone. Delta-aminolevuliinate synthase is the enzyme that catalyzes the interconversion between glycine and L-2-amino-3-oxobutanoic acid. Glycine C-acetyltransferase is also capable of catalyzing this reaction.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Amino-3-oxobutanoic acid	ChEBI
2-AMINO-3-ketobutyrIC ACID	ChEBI
L-2-Amino-3-oxobutanoate	ChEBI
L-2-Amino-acetoacetate	ChEBI
(S)-2-Amino-3-oxobutanoate	Generator
2-AMINO-3-ketobutyrate	Generator
L-2-Amino-acetoacetic acid	Generator
(2S)-2-amino-3-Oxobutanoate	HMDB
(2S)-2-amino-3-Oxobutanoic acid	HMDB
2-amino-3-Oxobutanoate	HMDB
2-amino-3-Oxobutanoic acid	HMDB
L-2-amino Acetic acid	HMDB

Chemical Formula

C₄H₇NO₃

Average Molecular Weight

117.1033

Monoisotopic Molecular Weight

117.042593095

IUPAC Name

(2S)-2-amino-3-oxobutanoic acid

Traditional Name

2-amino-3-ketobutyric acid

CAS Registry Number

6531-42-6

SMILES

CC(=O)[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C4H7NO3/c1-2(6)3(5)4(7)8/h3H,5H2,1H3,(H,7,8)/t3-/m0/s1

InChI Key

SAUCHDKDCUROAO-VKHMYHEASA-N

Chemical Taxonomy

Description

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

Substituents

L-alpha-amino acid
Beta-keto acid
Short-chain keto acid
Beta-hydroxy ketone
Keto acid
1,3-dicarbonyl compound
Alpha-aminoketone
Amino acid
Ketone
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:40673 )
2-amino-3-oxobutanoic acid (CHEBI:40673 )
Oxo fatty acids (C03508 )
Oxo fatty acids (LMFA01060172 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006454)

Cytoplasm (HMDB: HMDB0006454)

Source

Exogenous

Exogenous (HMDB: HMDB0006454)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006454)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glycine and Serine Metabolism (PathBank: SMP0087466)
Glycine and Serine Metabolism (HMDB: HMDB0006454)
Threonine Biosynthesis (PathBank: SMP0121292)
L-Threonine Degradation to Methylglyoxal (PathBank: SMP0002118)

Disease pathway

Sarcosinemia (PathBank: SMP0120521)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0120694)
Non-Ketotic Hyperglycinemia (PathBank: SMP0120534)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0120872)
Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0120695)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0120770)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006454)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	206 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.1	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.53 m³·mol⁻¹	ChemAxon
Polarizability	10.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon