MiMeDB: Showing metabocard for D-alpha-Aminobutyric acid (MMDBc0000131)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:00 UTC

Update Date

2024-10-13 08:57:20 UTC

Metabolite ID

MMDBc0000131

Metabolite Identification

Common Name

D-alpha-Aminobutyric acid

Description

D-alpha-Aminobutyric acid is the D-isomer of alpha-aminobutyric acid. The L-form of this amino acid is used in the biosynthesis of ophthalmic acid (a tripeptide analogue of glutathione in which the cysteine group is replaced by L-2-aminobutyrate, which was first discovered and isolated from calf lens). The D-form of this amino acid is a substrate for D-amino acid oxidase. There is little evidence that the D-form of this amino acid is found in human biofluids or tissues. What little does exist is likely of bacterial origin.

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

Molecular Formula

C₄H₉NO₂

Average Mass

103.1198

Monoisotopic Mass

103.063328537

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

2623-91-8

SMILES

Not Available

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

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Placenta
Saliva
Urine

Tissue Locations

Kidney
Liver
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human feces; Human vaginal secretion	Microbial culture

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	28306241
Plant		Pisum sativum	FooDB	Manually Annotated
Plant		Phaseolus vulgaris	FooDB	Manually Annotated

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Not Specified	Periodontal diseases	HMDB	20300169
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Not Specified	Pancreatic cancer	HMDB	20300169
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Female	Breast cancer	HMDB	20300169
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Both	Oral cancer	HMDB	20300169
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	20300169
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	26709303
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Urine	Detected and Quantified	0.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Placenta	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	20300169
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	26709303
Human Blood	Detected but not Quantified						HMDB

External Links

HMDB ID

HMDB0000650

DrugBank ID

DB04454

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012680

KNApSAcK ID

Not Available

Chemspider ID

388757

KEGG Compound ID

C02261

BioCyc ID

CPD0-1952

BiGG ID

Not Available

Wikipedia Link

Alpha-Aminobutyric acid

METLIN ID

Not Available

PubChem Compound

439691

PDB ID

Not Available

ChEBI ID

28797

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ketting D, Wadman SK, Spaapen LJ, Van der Meer SB, Duran M: Gas chromatography method for the separation of amino acids enantiomers in plasma and urine. Application in a case of short bowel syndrome. Clin Chim Acta. 1991 Dec 31;204(1-3):79-86. doi: 10.1016/0009-8981(91)90219-3. [PubMed:1819475 ]
Lange R, Hui Bon Hoa G, Douzou P, Yagi K: Kinetics of primary interaction of D-amino acid oxidase with its substrate. Biochem Int. 1983 May;6(5):693-8. [PubMed:6148943 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. doi: 10.1016/s1570-0232(03)00277-0. [PubMed:12829005 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for D-alpha-Aminobutyric acid (MMDBc0000131)

MOL for #<Metabolite:0x00007fdb2d8ad580>

3D MOL for #<Metabolite:0x00007fdb2d8ad580>

3D SDF for #<Metabolite:0x00007fdb2d8ad580>

3D-SDF for #<Metabolite:0x00007fdb2d8ad580>

PDB for #<Metabolite:0x00007fdb2d8ad580>

3D PDB for #<Metabolite:0x00007fdb2d8ad580>

SMILES for #<Metabolite:0x00007fdb2d8ad580>

INCHI for #<Metabolite:0x00007fdb2d8ad580>

Structure for #<Metabolite:0x00007fdb2d8ad580>

3D Structure for #<Metabolite:0x00007fdb2d8ad580>