ChemFOnt: Showing chemical card for D-alpha-Aminobutyric acid (CFc000000508)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:54 UTC

Chemfont ID

CFc000000508

Molecule Identification

Common Name

D-alpha-Aminobutyric acid

Definition

D-alpha-Aminobutyric acid (AABA), also known as alpha-aminobutyrate, (R)-2-aminobutanoic acid or D-homoalanine, belongs to the class of organic compounds known as D-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-alpha-aminobutyric acid is an optically active form of alpha-aminobutyric acid having D-configuration. It is an enantiomer of a L-alpha-aminobutyric acid and a non-proteinogenic amino acid. 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. Optically active organic compounds found in meteorites typically exist in racemic form, yet life on Earth has almost exclusively selected for L- over D-enantiomers of amino acids. D-enantiomers of non-proteinogenic amino acids are known to inhibit aerobic microorganisms. D-alpha-aminobutyric acid has been shown to inhibit microbial iron reduction by a number of Geobacter strains including Geobacter bemidjiensis, Geobacter metallireducens and Geopsychrobacter electrodiphilus (PMID: 25695622 ). D-alpha-Aminobutyric acid is a known substrate of D-amino acid oxidase (PMID: 6127341 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Aminobutyric acid	ChEBI
(R)-2-Aminobutanoic acid	ChEBI
(R)-2-Aminobutyric acid	ChEBI
alpha-Aminobutyric acid	ChEBI
D-(-)-2-Aminobutyric acid	ChEBI
D-2-Aminobutanoic acid	ChEBI
D-2-Aminobuttersaeure	ChEBI
D-2-Aminobutyrate	ChEBI
D-2-Aminobutyric acid	ChEBI
(2R)-2-Aminobutyrate	Generator
(R)-2-Aminobutanoate	Generator
(R)-2-Aminobutyrate	Generator
a-Aminobutyrate	Generator
a-Aminobutyric acid	Generator
alpha-Aminobutyrate	Generator
Α-aminobutyrate	Generator
Α-aminobutyric acid	Generator
D-(-)-2-Aminobutyrate	Generator
D-2-Aminobutanoate	Generator
D-a-Aminobutyrate	Generator
D-a-Aminobutyric acid	Generator
D-alpha-Aminobutyrate	Generator
D-Α-aminobutyrate	Generator
D-Α-aminobutyric acid	Generator
(2R)-2-Aminobutanoate	HMDB
(2R)-2-Aminobutanoic acid	HMDB
(R)-2-Amino-butanoate	HMDB
(R)-2-Amino-butanoic acid	HMDB
delta-(-)-2-Aminobutyric acid	HMDB
delta-2-Aminobutanoate	HMDB
delta-2-Aminobutanoic acid	HMDB
delta-2-Aminobuttersaeure	HMDB
delta-2-Aminobutyrate	HMDB
delta-2-Aminobutyric acid	HMDB
delta-alpha-Aminobutyric acid	HMDB
2R-Amino-butanoate	HMDB
(2S)-2-Aminobutanoic acid	HMDB
alpha-Aminobutyric acid, (S)-isomer	HMDB
Butyrine, (S)-isomer	HMDB
L-2-Aminobutyric acid	HMDB
Homoalanine	HMDB
2-Aminobutyric acid	HMDB
2-Aminobutanoic acid	HMDB
alpha-Aminobutyric acid, (+-)-isomer	HMDB
Butyrine, (R)-isomer	HMDB
Butyrine	HMDB
Butyrine, (+-)-isomer	HMDB
L-Homoalanine	HMDB
alpha-Aminobutyric acid, (R)-isomer	HMDB

Chemical Formula

C₄H₉NO₂

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

IUPAC Name

(2R)-2-aminobutanoic acid

Traditional Name

D-2-aminobutyric acid

CAS Registry Number

2623-91-8

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-/m1/s1

InChI Key

QWCKQJZIFLGMSD-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-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

D-alpha-amino acids

Alternative Parents

Substituents

D-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

D-alpha-amino acid (CHEBI:28797 )
alpha-aminobutyric acid (CHEBI:28797 )
Amino fatty acids (C02261 )
Amino fatty acids (LMFA01100043 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000650)
Saliva (PMID: 20300169)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 24029555)

Cellular substructure

Cytoplasm (HMDB: HMDB0000650)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000650)

Source

Endogenous

Endogenous (HMDB: HMDB0000650)

Plant

Plant (HMDB: HMDB0000650)
Fabaceae (HMDB: HMDB0000650)

Microbe

Microbe (HMDB: HMDB0000650)

Exogenous

Food

Food (HMDB: HMDB0000650)

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)

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Nut

Nuts (FooDB: FOOD00869)

Exogenous (HMDB: HMDB0000650)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000650)

Biological role

Drug metabolite (HMDB: HMDB0000650)

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	10.38 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