ChemFOnt: Showing chemical card for L-alpha-Aminobutyric acid (CFc000000346)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:43 UTC

Chemfont ID

CFc000000346

Molecule Identification

Common Name

L-alpha-Aminobutyric acid

Definition

L-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, or alpha-Aminobutyric acid, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alpha-Aminobutyric acid is a non-proteogenic amino acid that can be found in the human kidney, in liver tissues, and in most biofluids or excreta (e.g. feces, breast milk, urine, and blood). Within the cell, L-alpha-aminobutyric acid is primarily located in the cytoplasm. alpha-Aminobutyric acid is biosynthesized by transamination of oxobutyrate, a metabolite in isoleucine biosynthesis. As a non-proteogenic amino acid, alpha-aminobutyric acid can be used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing alpha-aminobutyric acid is ophthalmic acid, which was first isolated from calf lens. alpha-Aminobutyric acid is a non-essential amino acid that is primarily derived from the catabolism of methionine, threonine, and serine. High protein diets can result in significantly higher alpha-aminobutyrate levels in plasma (PMID: 26227325 ). alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency (PMID: 420125 ). alpha-Aminobutyric acid is one of the three isomers of aminobutyric acid. The two others are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-2-Aminobutyric acid	ChEBI
(2S)-2-Aminobutyric acid	ChEBI
(S)-2-Aminobutanoate	ChEBI
(S)-2-Aminobutanoic acid	ChEBI
(S)-2-Aminobutyric acid	ChEBI
L-(+)-2-Aminobutyric acid	ChEBI
L-2-Aminobuttersaeure	ChEBI
L-2-Aminobutyric acid	ChEBI
L-alpha-Amino-N-butyric acid	ChEBI
L-Butyrine	ChEBI
S-Butyrine	ChEBI
(-)-2-Aminobutyrate	Generator
(2S)-2-Aminobutyrate	Generator
(S)-2-Aminobutyrate	Generator
L-(+)-2-Aminobutyrate	Generator
L-2-Aminobutyrate	Generator
L-a-Amino-N-butyrate	Generator
L-a-Amino-N-butyric acid	Generator
L-alpha-Amino-N-butyrate	Generator
L-Α-amino-N-butyrate	Generator
L-Α-amino-N-butyric acid	Generator
L-a-Aminobutyrate	Generator
L-a-Aminobutyric acid	Generator
L-alpha-Aminobutyrate	Generator
L-Α-aminobutyrate	Generator
L-Α-aminobutyric acid	Generator
(+)-2-Aminobutanoate	HMDB
(+)-2-Aminobutanoic acid	HMDB
(+)-2-Aminobutyric acid	HMDB
(+)-alpha-Aminobutyric acid	HMDB
(2S)-2-Aminobutanoate	HMDB
(2S)-2-Aminobutanoic acid	HMDB, MeSH
(S)-(+)-alpha-Aminobutyric acid	HMDB
(S)-2-amino-Butanoate	HMDB
(S)-2-amino-Butanoic acid	HMDB
2-Aminobutanoate	HMDB
2-Aminobutanoic acid	HMDB, MeSH
2-Aminobutyrate	HMDB
2S-amino-Butanoate	HMDB, Generator
2S-amino-Butanoic acid	HMDB
alpha-Aminobutyric acid	HMDB, MeSH
L-2-amino-N-Butyric acid	HMDB
L-Ethylglycine	HMDB
Butyrine, (R)-isomer	MeSH, HMDB
2-Aminobutyric acid	MeSH, HMDB, Generator
alpha-Aminobutyric acid, (+-)-isomer	MeSH, HMDB
Butyrine	MeSH, HMDB
Butyrine, (S)-isomer	MeSH, HMDB
L-Homoalanine	MeSH, HMDB
alpha-Aminobutyric acid, (S)-isomer	MeSH, HMDB
Homoalanine	MeSH, HMDB
alpha-Aminobutyric acid, (R)-isomer	MeSH, HMDB
Butyrine, (+-)-isomer	MeSH, HMDB
L-2-Aminobutanoate	Generator, HMDB

Chemical Formula

C₄H₉NO₂

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

IUPAC Name

(2S)-2-aminobutanoic acid

Traditional Name

(-)-2-aminobutyric acid

CAS Registry Number

1492-24-6

SMILES

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

InChI Identifier

InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

QWCKQJZIFLGMSD-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
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:35619 )
alpha-aminobutyric acid (CHEBI:35619 )
Amino fatty acids (C02356 )
Amino fatty acids (LMFA01100034 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000452)

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000452)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12297216)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 12834252)
Breast milk (HMDB: HMDB0000452)
Cerebrospinal fluid (HMDB: HMDB0000452)

Organ

Kidney (HMDB: HMDB0000452)
Liver (HMDB: HMDB0000452)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 20669995)

Cellular substructure

Cytoplasm (HMDB: HMDB0000452)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000452)

Source

Exogenous

Exogenous (HMDB: HMDB0000452)

Food

Food (HMDB: HMDB0000452)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Endogenous

Endogenous (HMDB: HMDB0000452)

Plant

Fabaceae (HMDB: HMDB0000452)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0000452)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	358 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.3	ChemAxon
logS	0.54	ALOGPS
pKa (Strongest Acidic)	2.62	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.02 m³·mol⁻¹	ChemAxon
Polarizability	10.34 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

External Links

HMDB ID

HMDB0000452

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012537

KNApSAcK ID

Not Available

Chemspider ID

72524

KEGG Compound ID

C02356

BioCyc ID

CPD0-1942

BiGG ID

Not Available

Wikipedia Link

Alpha-Aminobutyric acid

METLIN ID

PubChem Compound

80283

PDB ID

Not Available

ChEBI ID

35619

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fotheringham, I. G.; Grinter, N.; Pantaleone, D. P.; Senkpeil, R. F.; Taylor, P. P. Engineering of a novel biochemical pathway for the biosynthesis of l-2-aminobutyric acid in Escherichia coli K12. Bioorganic & Medicinal Chemistry (1999), 7(10), 2209-2213.

Showing chemical card for L-alpha-Aminobutyric acid (CFc000000346)

MOL for CFc000000346 (L-alpha-Aminobutyric acid)

3D MOL for CFc000000346 (L-alpha-Aminobutyric acid)

3D SDF for CFc000000346 (L-alpha-Aminobutyric acid)

3D-SDF for CFc000000346 (L-alpha-Aminobutyric acid)

PDB for CFc000000346 (L-alpha-Aminobutyric acid)

3D PDB for CFc000000346 (L-alpha-Aminobutyric acid)

SMILES for CFc000000346 (L-alpha-Aminobutyric acid)

INCHI for CFc000000346 (L-alpha-Aminobutyric acid)

Structure for CFc000000346 (L-alpha-Aminobutyric acid)

3D Structure for CFc000000346 (L-alpha-Aminobutyric acid)