AFCDB: 4-Aminobutyric acid (FDB008937)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:19 UTC

Update date

2020-09-17 15:38:19 UTC

Primary ID

FDB008937

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Aminobutyric acid

Description

gamma-Aminobutyric acid, also known as GABA or g-amino-butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. gamma-Aminobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Aminobutyric acid exists in all living species, ranging from bacteria to humans. Outside of the human body, gamma-Aminobutyric acid has been detected, but not quantified in, several different foods, such as fox grapes, oxheart cabbages, garden onion (var.), yellow zucchinis, and chinese mustards. This could make gamma-aminobutyric acid a potential biomarker for the consumption of these foods. gamma-Aminobutyric acid is a potentially toxic compound. A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.

CAS Number

56-12-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	365 g/L	ALOGPS
logP	-3	ALOGPS
logP	-2.9	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	10.22	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	3	ChemAxon
Refractivity	25.46 m³·mol⁻¹	ChemAxon
Polarizability	10.62 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

Chemical Formula

C4H9NO2

IUPAC name

4-aminobutanoic acid

InChI Identifier

InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)

InChI Key

BTCSSZJGUNDROE-UHFFFAOYSA-N

Isomeric SMILES

NCCCC(O)=O

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

Classification

Description

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

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Amino fatty acid
Straight chain fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:16865 )
gamma-amino acid (CHEBI:16865 )
Amino fatty acids (C00334 )
Other amino acids (C00334 )
Biogenic amines (C00334 )
Amino fatty acids (LMFA01100039 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	203 oC
Boiling Point	Not Available
Experimental Water Solubility	1300 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.17	HANSCH,C ET AL. (1995)
Experimental pKa	4.05
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-dbf4f9e19a35f953a189	2014-09-20	View Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00dj-1900000000-f831f79dfcaeffa8b177	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-1900000000-2de9d92a2cfc7bc655f4	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-1900000000-73bbf2ee0803f058dbed	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-1901000000-85d4bd98af8534428b5a	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-0900000000-6be23968e972a414be51	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-9a224763afd8ca892add	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-9800000000-d8906d09ca1872a6391c	Spectrum
GC-MS	4-Aminobutyric acid, 2 TMS, GC-MS Spectrum	splash10-0udi-1900000000-54db7e21790401045519	Spectrum
GC-MS	4-Aminobutyric acid, 3 TMS, GC-MS Spectrum	splash10-00di-1901000000-b047af158215c2b5b8e8	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-001i-9000000000-21ea76dfb0da62031f1d	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-0901000000-5d60b0a446fd8122f613	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00dj-1900000000-f831f79dfcaeffa8b177	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-2de9d92a2cfc7bc655f4	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-73bbf2ee0803f058dbed	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1901000000-85d4bd98af8534428b5a	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-0900000000-6be23968e972a414be51	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-9a224763afd8ca892add	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-9800000000-d8906d09ca1872a6391c	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0udi-1900000000-54db7e21790401045519	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00di-1901000000-b047af158215c2b5b8e8	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-00dj-1900000000-1219470a0be188da64e6	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0900000000-f7117dfaf9d856c95919	Spectrum
GC-MS	4-Aminobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-e35585a985d8128d044e	Spectrum
Predicted GC-MS	4-Aminobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9000000000-d5f55a414ff1e8c65d9d	Spectrum
Predicted GC-MS	4-Aminobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-9700000000-4b2809309587240dd479	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uxr-8900000000-ce0d8f44422836cd9965	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0005-9000000000-8ce5afb97d7c08821da3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0005-9100000000-32c433b2c916697690f8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-5831aaabdf53f3132ae5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-9000000000-9babfd4a6937ecba7318	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-9000000000-e1c0c1485d846e9b123b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-647d55ecf98850e7a875	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-7c107641a38922c88fca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-86718b349efad6334e3a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-a1e84e55e4b6c6628d5d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0009000000-29c22bf0ed844d09c0af	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-1d00adad47e42c60c340	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-1900000000-47b195fb74720cc99464	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-9000000000-a14a52dc59bf9988bb44	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-5900000000-20c55b2809389d5ad83b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-eca4c5aefca98751a11e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-014j-9000000000-f0783316e09291749409	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0005-9000000000-81837eb9c0b926cb0e81	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0005-9000000000-8b48126992d7fa242636	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-9000000000-7d4636efbc4e5d75872e	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9100000000-655f9d93a35bfa537583	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ku-9000000000-4a334d5e272576f62403	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4a13b03446b3370ccd43	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9100000000-655f9d93a35bfa537583	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ku-9000000000-4a334d5e272576f62403	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16865

Phenol-Explorer ID

Not Available

DrugBank ID

DB02530

HMDB ID

HMDB00112

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

165

Dr. Duke ID

GABA|GAMMA-AMINOBUTYRIC-ACID

BIGG ID

34652

KNApSAcK ID

C00001337

HET ID

ABU

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1198861

SuperScent ID

Not Available

Wikipedia ID

GABA

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analeptic	35337	Any drug that enhances the activity of the central nervous system.	DUKE
anti cephalagic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cerebrotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti choreic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti insomniac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti insomnic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti lethargic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tinnitic			DUKE
anxiolytic	35474	Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.	DUKE
cardiovascular	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
central nervous system inhibitor	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
hypotensive			DUKE
neuro inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	DUKE
neurotransmitter	25512	An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
tranquilizer			DUKE

Enzymes

Name	Gene Name	UniProt ID
Glycine amidinotransferase, mitochondrial	GATM	P50440
4-aminobutyrate aminotransferase, mitochondrial	ABAT	P80404
Glutamate decarboxylase 2	GAD2	Q05329
Glutamate decarboxylase 1	GAD1	Q99259
Arginine decarboxylase	ADC	Q96A70
Glutamine synthetase	GLUL	P15104
Probable glutamate--tRNA ligase, mitochondrial	EARS2	Q5JPH6
Gamma-aminobutyric acid receptor-associated protein-like 2	GABARAPL2	P60520

Pathways

Name	SMPDB Link	KEGG Link
Glutamate Metabolism	SMP00072	map00250

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
savory	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
meaty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

4-Aminobutyric acid (FDB008937)

Structure for FDB008937 (4-Aminobutyric acid)