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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:51 UTC

HMDB ID

HMDB0000452

Secondary Accession Numbers

HMDB0000581
HMDB0005815
HMDB00452
HMDB00581
HMDB05815

Metabolite Identification

Common Name

L-alpha-Aminobutyric acid

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000452)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000452)

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000452)

Non-excretory biofluid

Biofluid or Excreta

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

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000452)
Urine (HMDB: HMDB0000452)

Organ

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

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000452)

Source

Endogenous

Endogenous (HMDB: HMDB0000452)

Plant

Fabaceae (HMDB: HMDB0000452)

Exogenous

Food

Food (HMDB: HMDB0000452)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0000452)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	291 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	143800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-3.17	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	121.191	31661259
DarkChem	[M-H]-	117.336	31661259
AllCCS	[M+H]+	127.387	32859911
AllCCS	[M-H]-	123.325	32859911
DeepCCS	[M+H]+	121.502	30932474
DeepCCS	[M-H]-	118.702	30932474
DeepCCS	[M-2H]-	155.223	30932474
DeepCCS	[M+Na]+	129.938	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.6	32859911
AllCCS	[M-H]-	123.3	32859911
AllCCS	[M+Na-2H]-	127.2	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-alpha-Aminobutyric acid	CC[C@H](N)C(O)=O	1783.7	Standard polar	33892256
L-alpha-Aminobutyric acid	CC[C@H](N)C(O)=O	971.1	Standard non polar	33892256
L-alpha-Aminobutyric acid	CC[C@H](N)C(O)=O	1416.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-alpha-Aminobutyric acid,1TMS,isomer #1	CC[C@H](N)C(=O)O[Si](C)(C)C	1033.7	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,1TMS,isomer #2	CC[C@H](N[Si](C)(C)C)C(=O)O	1141.2	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1	CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1185.8	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1	CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1198.3	Standard non polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #1	CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1318.6	Standard polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1357.8	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1241.7	Standard non polar	33892256
L-alpha-Aminobutyric acid,2TMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1478.6	Standard polar	33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1418.9	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1319.2	Standard non polar	33892256
L-alpha-Aminobutyric acid,3TMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1311.7	Standard polar	33892256
L-alpha-Aminobutyric acid,1TBDMS,isomer #1	CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1253.8	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,1TBDMS,isomer #2	CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1379.2	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1	CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1605.1	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1	CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1617.8	Standard non polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #1	CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1614.9	Standard polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1780.1	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1682.0	Standard non polar	33892256
L-alpha-Aminobutyric acid,2TBDMS,isomer #2	CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1685.8	Standard polar	33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2044.3	Semi standard non polar	33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1965.0	Standard non polar	33892256
L-alpha-Aminobutyric acid,3TBDMS,isomer #1	CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1739.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0900000000-5659d6d78898cfc7e3e1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (2 TMS)	splash10-001i-0900000000-c8849b7c3a366e6c4cb8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (3 TMS)	splash10-0udi-0790000000-70b33ceb8fc59cf98fc5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-EI-TOF (Non-derivatized)	splash10-001i-0900000000-5659d6d78898cfc7e3e1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized)	splash10-0udi-0790000000-70b33ceb8fc59cf98fc5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized)	splash10-001i-0900000000-c8849b7c3a366e6c4cb8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-231d9b85dacdfc8cfa1a	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9500000000-47e250b31bdc60f6848c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-alpha-Aminobutyric acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0900000000-01184422112c4f45d2c2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0udi-0900000000-771c55fe95bc80e67d59	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0udi-1900000000-ddc187aaa752f4b10f2b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-9000000000-3bdaa058b45a133c3bbd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0udi-0900000000-02624b93137883b214ad	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0900000000-01184422112c4f45d2c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0900000000-771c55fe95bc80e67d59	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-1900000000-ddc187aaa752f4b10f2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-3bdaa058b45a133c3bbd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF , negative-QTOF	splash10-0udi-0900000000-02624b93137883b214ad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-9100000000-ee8abbcaf7c2b98fbbf2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4l-9000000000-1345dd328d7b79523e9b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-052f-9100000000-338f85ef5403099a76c7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0udi-5900000000-116db8b71549d033ab56	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0a4i-9000000000-4ce723a5a5c9873c57dd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0a4i-9000000000-7cce1c626271fbc1ff33	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-052f-9000000000-d7ee22bb360494f5a6ed	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0006-9000000000-e3892ebe321e35491da7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0a4i-9200000000-c71bee21cc5879ab61bb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , positive-QTOF	splash10-0udi-5900000000-10bf801074f410f1316f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-8d75ea4bc446938a682e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-7cce1c626271fbc1ff33	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , positive-QTOF	splash10-052f-9000000000-d7ee22bb360494f5a6ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-e3892ebe321e35491da7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-alpha-Aminobutyric acid LC-ESI-QTOF , positive-QTOF	splash10-0a4i-9200000000-c71bee21cc5879ab61bb	2017-09-14	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	23.0 (15.0-31.0) uM	Adult (>18 years old)	Both	Normal	12297216	details
Blood	Detected and Quantified	21.0 +/- 5.0 uM	Adult (>18 years old)	Both	Normal	16087168	details
Blood	Detected and Quantified	24.0 +/- 6.0 uM	Children (1-13 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Blood	Detected and Quantified	25.0 +/- 5.0 uM	Adult (>18 years old)	Male	Normal	6198473	details
Blood	Detected and Quantified	21.0 +/- 7.0 uM	Adult (>18 years old)	Female	Normal	6198473	details
Breast Milk	Detected and Quantified	17.7 +/- 6.9 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.3 +/- 1.4 uM	Adult (>18 years old)	Not Specified	Normal	6198473	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.5 +/- 2.2 uM	Adult (>18 years old)	Not Specified	Normal	6198473	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	3.33 (1.80-4.86) uM	Adult (>18 years old)	Both	Normal	12834252	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	26709303	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	1.13 +/- 4.52 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	3.392 +/- 6.78 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	6.784 +/- 5.65 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	<3.39 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	0.46-1.1 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	1.1 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	2.97 +/- 1.828 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	<3.51 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<2.15 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	0.032 (0.0-0.065) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.52-0.71 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	<7.13 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	1.37 +/- 1.05 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	2.2 (1.1-4.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	<6.33 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22148915	details
Urine	Detected and Quantified	0.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected and Quantified	0.045 +/- 0.045 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19075476	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Urine	Detected and Quantified	<4.30 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected and Quantified	24.0 +/- 3.0 uM	Adult (>18 years old)	Both	Kidney disease	16087168	details
Blood	Detected and Quantified	19.79 +/- 2.17 uM	Adult (>18 years old)	Both	Alzheimer's disease	17031479	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	7.404 +/- 7.874 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	22148915	details
Urine	Detected and Quantified	1.27 +/- 2.4 umol/mmol creatinine	Adult (>18 years old)	Both	Bone metastases	19075476	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Kidney disease
Chuang CK, Lin SP, Chen HH, Chen YC, Wang TJ, Shieh WH, Wu CJ: Plasma free amino acids and their metabolites in Taiwanese patients on hemodialysis and continuous ambulatory peritoneal dialysis. Clin Chim Acta. 2006 Feb;364(1-2):209-16. Epub 2005 Aug 8. [PubMed:16087168 ]
Schizophrenia
Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Cancer with metastatic bone disease
Tsuruta Y, Matsumoto M, Inoue H, Munemura S, Yamano S, Iguchi H: Determination of N-ethylglycine in urine of cancer patients with metastatic bone disease by HPLC using 4-(5,6-dimethoxy-2-phthalimidinyl)-2-methoxyphenylsulfonyl chloride as a fluorescent labeling reagent. Anal Sci. 2008 Dec;24(12):1629-31. [PubMed:19075476 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

104300 (Alzheimer's disease)
181500 (Schizophrenia)
610247 (Eosinophilic esophagitis)
114500 (Colorectal cancer)

External Links

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

VMH ID

C02356

MarkerDB ID

Not Available

Good Scents ID

rw1141141

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. [PubMed:3918815 ]
Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed:9267323 ]
Oishi M, Mochizuki Y, Sanuki E: [Regional cerebral blood flow and cerebrospinal fluid amino acid analysis in elderly dementia]. No To Shinkei. 1998 Nov;50(11):1018-21. [PubMed:9866128 ]
Haschke-Becher E, Kainz A, Bachmann C: Reference values of amino acids and of common clinical chemistry in plasma of healthy infants aged 1 and 4 months. J Inherit Metab Dis. 2016 Jan;39(1):25-37. doi: 10.1007/s10545-015-9870-4. Epub 2015 Jul 31. [PubMed:26227325 ]
Yudkoff M, Blazer-Yost B, Cohn R, Segal S: On the clinical significance of the plasma alpha-amino-n-butyric acid:leucine ratio. Am J Clin Nutr. 1979 Feb;32(2):282-5. [PubMed:420125 ]

Enzymes

Enzyme Details

1. Glycine amidinotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:: GATM
Uniprot ID:: P50440
Molecular weight:: 48455.01

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. Pro-epidermal growth factor

General function:: Involved in calcium ion binding
Specific function:: EGF stimulates the growth of various epidermal and epithelial tissues in vivo and in vitro and of some fibroblasts in cell culture. Magnesiotropic hormone that stimulates magnesium reabsorption in the renal distal convoluted tubule via engagement of EGFR and activation of the magnesium channel TRPM6
Gene Name:: EGF
Uniprot ID:: P01133
Molecular weight:: 133993.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for L-alpha-Aminobutyric acid (HMDB0000452)

MOL for HMDB0000452 (L-alpha-Aminobutyric acid)

3D MOL for HMDB0000452 (L-alpha-Aminobutyric acid)

3D SDF for HMDB0000452 (L-alpha-Aminobutyric acid)

3D-SDF for HMDB0000452 (L-alpha-Aminobutyric acid)

PDB for HMDB0000452 (L-alpha-Aminobutyric acid)

3D PDB for HMDB0000452 (L-alpha-Aminobutyric acid)

SMILES for HMDB0000452 (L-alpha-Aminobutyric acid)

INCHI for HMDB0000452 (L-alpha-Aminobutyric acid)

Structure for HMDB0000452 (L-alpha-Aminobutyric acid)

3D Structure for HMDB0000452 (L-alpha-Aminobutyric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References