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Showing Compound L-2-Aminobutanoic acid (FDB012537)

Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:07:00 UTC
Primary IDFDB012537
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-2-Aminobutanoic acid
DescriptionL-alpha-Aminobutyric acid, also known as (2S)-2-aminobutyrate or (S)-2-aminobutanoic acid, 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. L-alpha-Aminobutyric acid is found, on average, in the highest concentration within milk (cow). L-alpha-Aminobutyric acid has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), common peas (Pisum sativum), and domestic pigs (Sus scrofa domestica). This could make L-alpha-aminobutyric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on L-alpha-Aminobutyric acid.
CAS Number1492-24-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-2-Aminobutyric acidChEBI
(2S)-2-Aminobutyric acidChEBI
(S)-2-AminobutanoateChEBI
(S)-2-Aminobutanoic acidChEBI
(S)-2-Aminobutyric acidChEBI
L-(+)-2-Aminobutyric acidChEBI
L-2-AminobuttersaeureChEBI
L-2-Aminobutyric acidChEBI
L-alpha-Amino-N-butyric acidChEBI
L-ButyrineChEBI
S-ButyrineChEBI
(-)-2-AminobutyrateGenerator
(2S)-2-AminobutyrateGenerator
(S)-2-AminobutyrateGenerator
L-(+)-2-AminobutyrateGenerator
L-2-AminobutyrateGenerator
L-a-Amino-N-butyrateGenerator
L-a-Amino-N-butyric acidGenerator
L-alpha-Amino-N-butyrateGenerator
L-Α-amino-N-butyrateGenerator
L-Α-amino-N-butyric acidGenerator
L-a-AminobutyrateGenerator
L-a-Aminobutyric acidGenerator
L-alpha-AminobutyrateGenerator
L-Α-aminobutyrateGenerator
L-Α-aminobutyric acidGenerator
(+)-2-AminobutanoateHMDB
(+)-2-Aminobutanoic acidHMDB
(+)-2-Aminobutyric acidHMDB
(+)-alpha-Aminobutyric acidHMDB
(2S)-2-AminobutanoateHMDB
(2S)-2-Aminobutanoic acidHMDB, MeSH
(S)-(+)-alpha-Aminobutyric acidHMDB
(S)-2-amino-ButanoateHMDB
(S)-2-amino-Butanoic acidHMDB
2-AminobutanoateHMDB
2-Aminobutanoic acidHMDB, MeSH
2-AminobutyrateHMDB
2S-amino-ButanoateHMDB, Generator
2S-amino-Butanoic acidHMDB
alpha-Aminobutyric acidHMDB, MeSH
L-2-amino-N-Butyric acidHMDB
L-EthylglycineHMDB
Butyrine, (R)-isomerMeSH, HMDB
2-Aminobutyric acidMeSH, HMDB, Generator
alpha-Aminobutyric acid, (+-)-isomerMeSH, HMDB
ButyrineMeSH, HMDB
Butyrine, (S)-isomerMeSH, HMDB
L-HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (S)-isomerMeSH, HMDB
HomoalanineMeSH, HMDB
alpha-Aminobutyric acid, (R)-isomerMeSH, HMDB
Butyrine, (+-)-isomerMeSH, HMDB
L-2-AminobutanoateGenerator, HMDB
2-Aminobutanoic acid, 9CI; L-formdb_source
2-Aminobutyric acid, L-biospider
AABAmanual
Alpha-Aminobutyric acidbiospider
Butanoic acid, 2-amino-, (2S)-biospider
Butanoic acid, 2-amino-, (S)- (9CI)biospider
Butyric acid, 2-amino-, L- (8CI)biospider
L-α-Amino-n-butyric acidbiospider
L-α-Aminobutyratebiospider
L-α-Aminobutyric acidbiospider
L-2-Amino-n-butyric acidbiospider
L-a-amino-N-ButyrateGenerator
L-a-amino-N-Butyric acidGenerator
L-AABAmanual
L-alpha-amino-N-ButyrateGenerator
L-alpha-Amino-n-butyric acidbiospider
L-alpha-Aminobutyric acidbiospider
L-butyrinemanual
L-α-amino-N-butyrateGenerator
L-α-amino-N-butyric acidGenerator
L-α-aminobutyrateGenerator
L-α-aminobutyric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility358 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.54ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.02 m³·mol⁻¹ChemAxon
Polarizability10.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H9NO2
IUPAC name(2S)-2-aminobutanoic acid
InChI IdentifierInChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N
Isomeric SMILESCC[C@H](N)C(O)=O
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 46.59%; H 8.80%; N 13.58%; O 31.03%DFC
Melting PointMp 292 dec. (303° in sealed tube)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.17HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +8 (H2O) (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-2-Aminobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-5659d6d78898cfc7e3e1Spectrum
GC-MSL-2-Aminobutanoic acid, 2 TMS, GC-MS Spectrumsplash10-001i-0900000000-c8849b7c3a366e6c4cb8Spectrum
GC-MSL-2-Aminobutanoic acid, 3 TMS, GC-MS Spectrumsplash10-0udi-0790000000-70b33ceb8fc59cf98fc5Spectrum
GC-MSL-2-Aminobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-5659d6d78898cfc7e3e1Spectrum
GC-MSL-2-Aminobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0790000000-70b33ceb8fc59cf98fc5Spectrum
GC-MSL-2-Aminobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-c8849b7c3a366e6c4cb8Spectrum
Predicted GC-MSL-2-Aminobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9000000000-231d9b85dacdfc8cfa1aSpectrum
Predicted GC-MSL-2-Aminobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9500000000-47e250b31bdc60f6848cSpectrum
Predicted GC-MSL-2-Aminobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-2-Aminobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-2-Aminobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-2-Aminobutanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-01184422112c4f45d2c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-771c55fe95bc80e67d592012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ddc187aaa752f4b10f2b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-3bdaa058b45a133c3bbd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-02624b93137883b214ad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-01184422112c4f45d2c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-771c55fe95bc80e67d592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ddc187aaa752f4b10f2b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-3bdaa058b45a133c3bbd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-02624b93137883b214ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9100000000-ee8abbcaf7c2b98fbbf22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-1345dd328d7b79523e9b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9100000000-338f85ef5403099a76c72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-5900000000-116db8b71549d033ab562012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9000000000-4ce723a5a5c9873c57dd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-7cce1c626271fbc1ff332012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-052f-9000000000-d7ee22bb360494f5a6ed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-e3892ebe321e35491da72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-9200000000-c71bee21cc5879ab61bb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-5900000000-10bf801074f410f1316f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-8d75ea4bc446938a682e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-7cce1c626271fbc1ff332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052f-9000000000-d7ee22bb360494f5a6ed2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-e3892ebe321e35491da72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-9200000000-c71bee21cc5879ab61bb2017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID72524
ChEMBL IDCHEMBL1230782
KEGG Compound IDC02356
Pubchem Compound ID80283
Pubchem Substance IDNot Available
ChEBI ID35619
Phenol-Explorer IDNot Available
DrugBank IDDB04454
HMDB IDHMDB00452
CRC / DFC (Dictionary of Food Compounds) IDHJR33-A:HHT92-N
EAFUS IDNot Available
Dr. Duke IDL-(+)-2-AMINOBUTYRIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDABA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAlpha-Aminobutyric_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine amidinotransferase, mitochondrialGATMP50440
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).