ChemFOnt: Showing chemical card for 3-Aminoisobutanoic acid (CFc000001990)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:45 UTC

Chemfont ID

CFc000001990

Molecule Identification

Common Name

3-Aminoisobutanoic acid

Definition

3-Aminoisobutanoic acid, also known as b-aminoisobutyrate or 2-methyl-beta-alanine, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. 3-Aminoisobutanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 3-Aminoisobutanoic acid exists in all eukaryotes, ranging from yeast to humans. 3-aminoisobutanoic acid can be biosynthesized from ureidoisobutyric acid; which is mediated by the enzyme Beta-ureidopropionase. In humans, 3-aminoisobutanoic acid is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Beta-ureidopropionase deficiency is an inborn error of pyrimidine degradation associated with neurological abnormalities (OMIM 606673 ). 3-Aminoisobutanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Aminomethyl)propionic acid	ChEBI
2-Methyl-beta-alanine	ChEBI
3-Amino-2-methylpropanoate	ChEBI
3-Aminoisobutanoate	ChEBI
alpha-Methyl-beta-alanine	ChEBI
BAIB	ChEBI
beta-Aminoisobutyric acid	ChEBI
DL-beta-Aminoisobutyric acid	ChEBI
2-(Aminomethyl)propionate	Generator
2-Methyl-b-alanine	Generator
2-Methyl-β-alanine	Generator
3-Amino-2-methylpropanoic acid	Generator
a-Methyl-b-alanine	Generator
Α-methyl-β-alanine	Generator
b-Aminoisobutyrate	Generator
b-Aminoisobutyric acid	Generator
beta-Aminoisobutyrate	Generator
Β-aminoisobutyrate	Generator
Β-aminoisobutyric acid	Generator
DL-b-Aminoisobutyrate	Generator
DL-b-Aminoisobutyric acid	Generator
DL-beta-Aminoisobutyrate	Generator
DL-Β-aminoisobutyrate	Generator
DL-Β-aminoisobutyric acid	Generator
3-Aminoisobutyric acid	HMDB
(+/-)-3-amino-2-methylpropanoate	HMDB
(+/-)-3-amino-2-methylpropanoic acid	HMDB
(+/-)-3-aminoisobutyric acid	HMDB
(+/-)-b-aminoisobutyric acid	HMDB
(+/-)-beta-aminoisobutyric acid	HMDB
3-Amino-isobutanoate	HMDB
3-Amino-isobutanoic acid	HMDB
DL-2-Methyl-b-alanine	HMDB
DL-2-Methyl-beta-alanine	HMDB
DL-3-Amino-2-methylpropionic acid	HMDB
DL-3-Aminoisobutyric acid	HMDB
3-Aminoisobutyric acid, (+-)-isomer	HMDB
DL-3-Aminoisobutyric acid monohydrate	HMDB
3-Aminoisobutyric acid, (S)-isomer	HMDB
3-Aminoisobutyric acid, tritium-labeled	HMDB
3-Aminoisobutyric acid, (R)-isomer	HMDB
3-Aminoisobutyrate	HMDB
3-Aminoisobutanoic acid	ChEBI

Chemical Formula

C₄H₉NO₂

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

IUPAC Name

3-amino-2-methylpropanoic acid

Traditional Name

(+)-β-aminoisobutyric acid

CAS Registry Number

144-90-1

SMILES

CC(CN)C(O)=O

InChI Identifier

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

InChI Key

QCHPKSFMDHPSNR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta 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

Beta amino acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-amino acid (CHEBI:27389 )
Other amino acids (C05145 )
Amino fatty acids (LMFA01100054 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 679461)

Organ

Placenta (HMDB: HMDB0003911)

Excreta

Biofluid or Excreta

Urine (PMID: 679461)
Feces (PMID: 25486321)

Cellular substructure

Cytoplasm (HMDB: HMDB0003911)
Membrane (HMDB: HMDB0003911)

Source

Endogenous

Endogenous (HMDB: HMDB0003911)

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)

Process

Role

Biological role

Metabolite (HMDB: HMDB0003911)
Metabolite (HMDB: HMDB0003911)

Industrial application

Pharmaceutical industry

Biomarker

Aldehyde dehydrogenase deficiency (MarkerDB: MDB00000435)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	367 g/L	ALOGPS
logP	-3	ALOGPS
logP	-2.6	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	10.32	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	25.28 m³·mol⁻¹	ChemAxon
Polarizability	10.42 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

HMDB0003911

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023248

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

3-Aminoisobutyric_acid

METLIN ID

5472

PubChem Compound

64956

PDB ID

Not Available

ChEBI ID

27389

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Balenovic, K.; Jambresic, I.; Ranogajec, I. Preparation of b-aminoisobutyric acid from glycine via the Wolff rearrangement of diazoethyl ketones. Croatica Chemica Acta (1957), 29 87-92.

Showing chemical card for 3-Aminoisobutanoic acid (CFc000001990)

MOL for CFc000001990 (3-Aminoisobutanoic acid)

3D MOL for CFc000001990 (3-Aminoisobutanoic acid)

3D SDF for CFc000001990 (3-Aminoisobutanoic acid)

3D-SDF for CFc000001990 (3-Aminoisobutanoic acid)

PDB for CFc000001990 (3-Aminoisobutanoic acid)

3D PDB for CFc000001990 (3-Aminoisobutanoic acid)

SMILES for CFc000001990 (3-Aminoisobutanoic acid)

INCHI for CFc000001990 (3-Aminoisobutanoic acid)

Structure for CFc000001990 (3-Aminoisobutanoic acid)

3D Structure for CFc000001990 (3-Aminoisobutanoic acid)