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Identification
YMDB IDYMDB00489
Name4-Acetamidobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Acetamidobutanoic acid, also known as N4-acetylaminobutanoate or N-acetyl-4-aminobutyric acid, 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. 4-Acetamidobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Acetamidobutanoic acid exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • -Acetylaminobutyric acid
  • 4-(Acetylamino)butanoate
  • 4-(Acetylamino)butanoic acid
  • 4-(acetylamino)butyrate
  • 4-Acetamidobutanoate
  • 4-acetamidobutyrate
  • 4-Acetamidobutyric acid
  • Butanoic acid, 4-(acetylamino)-
  • Butyric acid, 4-acetamido-
  • N-Acetyl-4-aminobutanoate
  • N-Acetyl-4-aminobutanoic acid
  • N-acetyl-4-aminobutyrate
  • N-Acetyl-4-aminobutyric acid
  • N-acetyl-GABA
  • N-acetyl-gamma-amino-n-butyric acid
  • N-acetyl-gamma-aminobutyrate
  • N4-Acetylaminobutanoate
  • N4-Acetylaminobutanoic acid
  • 4-Acetamidobutanoic acid
CAS number3025-96-5
WeightAverage: 145.1564
Monoisotopic: 145.073893223
InChI KeyUZTFMUBKZQVKLK-UHFFFAOYSA-N
InChIInChI=1S/C6H11NO3/c1-5(8)7-4-2-3-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
IUPAC Name4-acetamidobutanoic acid
Traditional IUPAC Name4-acetamidobutyrate
Chemical FormulaC6H11NO3
SMILESCC(=O)NCCCC(O)=O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Straight chain fatty acid
  • Fatty acid
  • Fatty acyl
  • Carboximidic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboximidic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility19.9 g/LALOGPS
logP-0.48ALOGPS
logP-0.8ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.9 m³·mol⁻¹ChemAxon
Polarizability14.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
water + 4-Acetamidobutanoic acidAcetic acid + gamma-Aminobutyric acid
NAD + 4-acetamidobutanal + waterNADH + 4-Acetamidobutanoic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17645
HMDB IDHMDB03681
Pubchem Compound ID6991994
Kegg IDC02946
ChemSpider ID17180
FOODB IDFDB023214
Wikipedia IDNot Available
BioCyc IDCPD-570