gamma-amino-gamma-cyanobutanoic acid (YMDB00784)

Identification

YMDB ID

YMDB00784

Name

gamma-amino-gamma-cyanobutanoic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

gamma-amino-gamma-cyanobutanoic acid, also known as g-amino-g-cyanobutanoate or 4-amino-4-cyanobutyric 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. gamma-amino-gamma-cyanobutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-amino-gamma-cyanobutanoic acid may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

4-Amino-4-cyanobutanoic acid
4-amino-4-cyanobutyric acid
gamma-Amino-gamma-cyanobutanoate
4-Amino-4-cyanobutanoate
4-Amino-4-cyanobutyrate
g-Amino-g-cyanobutanoate
g-Amino-g-cyanobutanoic acid
Γ-amino-γ-cyanobutanoate
Γ-amino-γ-cyanobutanoic acid
gamma-amino-gamma-Cyanobutanoic acid

CAS number

14046-56-1

Weight

Average: 128.1292
Monoisotopic: 128.05857751

InChI Key

DXWQLTOXWVWMOH-UHFFFAOYSA-N

InChI

InChI=1S/C5H8N2O2/c6-3-4(7)1-2-5(8)9/h4H,1-2,7H2,(H,8,9)

IUPAC Name

4-amino-4-cyanobutanoic acid

Traditional IUPAC Name

4-amino-4-cyanobutyric acid

Chemical Formula

C₅H₈N₂O₂

SMILES

NC(CCC(O)=O)C#N

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.

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
Fatty acid
Fatty acyl
Alpha-aminonitrile
Amino acid
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:28474 )
gamma-amino acid (CHEBI:28474 )
aliphatic nitrile (CHEBI:28474 )
Amino fatty acids (C05715 )
Cyano fatty acids (C05715 )
Amino fatty acids (LMFA01100037 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	25.2 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.1	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	6.71	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.27 m³·mol⁻¹	ChemAxon
Polarizability	12.35 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

extracellular
cell envelope
mitochondrion
endoplasmic reticulum
lipid particle

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Cyanoamino acid metabolism

ec00460

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-3057eb89e7bf0040eeb1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-3900000000-346d927b53214ab76588	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xr-9400000000-dc60205db2ddd7c7a661	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-ea897d3f308b7f67ac6b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-d9224a8694bce09e8228	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-7900000000-40ba92498fb3527bb4e8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-9b904d46ac276c48104d	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
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	28474
HMDB ID	Not Available
Pubchem Compound ID	440769
Kegg ID	C05715
ChemSpider ID	389638
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

gamma-amino-gamma-cyanobutanoic acid (YMDB00784)

Structure for #<Compound:0xaed57c54>