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

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

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

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	473.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	365.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	40.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	242.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	294.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	342.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	537.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	704.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	726.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	208.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	464.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	222.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	59.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	355.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	632.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	60.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	274.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (void)	2025-10-23	669.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	600.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_1	CC[C@@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2409.46
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_2	CC[C@@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1911.96
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_3	CC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2158.16
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_4	CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2089.2
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_5	CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1611.72
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_1	CC[C@@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2299.34
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_2	CC[C@@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2089.63
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_3	CC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2298.29
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_4	CC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2344.96
Gas Chromatography	D-alpha-Aminobutyric acid_TMS_5	CC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1559.51

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Firmicutes	3	Human feces; Human vaginal secretion	Microbial culture

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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:0x00007f2df4851488>

3D MOL for #<Metabolite:0x00007f2df4851488>

3D SDF for #<Metabolite:0x00007f2df4851488>

3D-SDF for #<Metabolite:0x00007f2df4851488>

PDB for #<Metabolite:0x00007f2df4851488>

3D PDB for #<Metabolite:0x00007f2df4851488>

SMILES for #<Metabolite:0x00007f2df4851488>

INCHI for #<Metabolite:0x00007f2df4851488>

Structure for #<Metabolite:0x00007f2df4851488>

3D Structure for #<Metabolite:0x00007f2df4851488>