2-Aminobutyrate (YMDB01570)

Identification

YMDB ID

YMDB01570

Name

2-Aminobutyrate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

L-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid or (2S)-2-aminobutyrate, 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. L-alpha-Aminobutyric acid exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on L-alpha-Aminobutyric acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-2-Aminobutyrate
(-)-2-Aminobutyric acid
(+)-2-Aminobutanoate
(+)-2-Aminobutanoic acid
(+)-2-Aminobutyric acid
(+)-alpha-Aminobutyric acid
(2S)-2-Aminobutanoate
(2S)-2-Aminobutanoic acid
(2S)-2-Aminobutyrate
(2S)-2-Aminobutyric acid
(S)-(+)-alpha-Aminobutyric acid
(S)-2-amino-Butanoate
(S)-2-amino-Butanoic acid
(S)-2-Aminobutanoic acid
(S)-2-Aminobutyrate
(S)-2-Aminobutyric acid
2-Aminobutanoate
2-Aminobutanoic acid
2-Aminobutyrate
2-Aminobutyric acid
2S-amino-Butanoate
2S-amino-Butanoic acid
alpha-Aminobutyric acid
alpha-Aminobutyric acid, (+-)-isomer
alpha-Aminobutyric acid, (R)-isomer
alpha-Aminobutyric acid, (S)-isomer
Butyrine
Butyrine, (+-)-isomer
Butyrine, (R)-isomer
Butyrine, (S)-isomer
Homoalanine
L-(+)-2-Aminobutyrate
L-(+)-2-Aminobutyric acid
L-2-amino-N-Butyric acid
L-2-Aminobuttersaeure
L-2-Aminobutyrate
L-2-Aminobutyric acid
L-a-amino-N-Butyrate
L-a-amino-N-Butyric acid
L-a-Aminobutyric acid
L-alpha-amino-N-Butyrate
L-alpha-amino-N-Butyric acid
L-alpha-Aminobutyrate
L-Butyrine
L-Ethylglycine
L-Homoalanine
L-α-amino-N-butyrate
L-α-amino-N-butyric acid
S-Butyrine
(S)-2-Aminobutanoate
L-a-Aminobutyrate
L-Α-aminobutyrate
L-Α-aminobutyric acid
L-2-Aminobutanoate

CAS number

1492-24-6

Weight

Average: 103.1198
Monoisotopic: 103.063328537

InChI Key

QWCKQJZIFLGMSD-VKHMYHEASA-N

InChI

InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

IUPAC Name

(2S)-2-aminobutanoic acid

Traditional IUPAC Name

(-)-2-aminobutyric acid

Chemical Formula

C₄H₉NO₂

SMILES

CC[C@H](N)C(O)=O

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 )

Physical Properties

State

Solid

Charge

Melting point

291 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	-3.17 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
875 ± 44 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0900000000-5659d6d78898cfc7e3e1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-0900000000-c8849b7c3a366e6c4cb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-0790000000-70b33ceb8fc59cf98fc5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0900000000-5659d6d78898cfc7e3e1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0790000000-70b33ceb8fc59cf98fc5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0900000000-c8849b7c3a366e6c4cb8	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-231d9b85dacdfc8cfa1a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9500000000-47e250b31bdc60f6848c	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-01184422112c4f45d2c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-771c55fe95bc80e67d59	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-ddc187aaa752f4b10f2b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-3bdaa058b45a133c3bbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-02624b93137883b214ad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-01184422112c4f45d2c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-771c55fe95bc80e67d59	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-ddc187aaa752f4b10f2b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-3bdaa058b45a133c3bbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-02624b93137883b214ad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-9100000000-ee8abbcaf7c2b98fbbf2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9000000000-1345dd328d7b79523e9b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9100000000-338f85ef5403099a76c7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-5900000000-116db8b71549d033ab56	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4i-9000000000-4ce723a5a5c9873c57dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9000000000-7cce1c626271fbc1ff33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-052f-9000000000-d7ee22bb360494f5a6ed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-e3892ebe321e35491da7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-9200000000-c71bee21cc5879ab61bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-5900000000-10bf801074f410f1316f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-8d75ea4bc446938a682e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-7cce1c626271fbc1ff33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052f-9000000000-d7ee22bb360494f5a6ed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-e3892ebe321e35491da7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-9200000000-c71bee21cc5879ab61bb	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	35619
HMDB ID	HMDB00452
Pubchem Compound ID	80283
Kegg ID	C02356
ChemSpider ID	72524
FOODB ID	FDB012537
Wikipedia ID	Alpha-Aminobutyric acid
BioCyc ID	Not Available

Structure for #<Compound:0xaab6a8a0>