Bovine Metabolome Database: Showing metabocard for L-3-Cyanoalanine (BMDB0109670)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2020-05-05 15:49:34 UTC

Update Date

2020-05-05 18:40:49 UTC

BMDB ID

BMDB0109670

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-3-Cyanoalanine

Description

L-3-Cyanoalanine, also known as L-beta-cyanoalanine, 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-3-Cyanoalanine is a very strong basic compound (based on its pKa). L-3-Cyanoalanine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, L-3-Cyanoalanine has been detected, but not quantified in, several different foods, such as summer savories, orange bell peppers, red rices, mixed nuts, and green bell peppers. This could make L-3-cyanoalanine a potential biomarker for the consumption of these foods. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
L-beta-Cyanoalanine	ChEBI, KEGG
L-b-Cyanoalanine	Generator
L-β-Cyanoalanine	Generator
beta-Cyanoalanine	MeSH, HMDB
3-Cyanoalanine	MeSH, HMDB
beta-Cyano-L-alanine	MeSH, HMDB
3-Cyanoalanine, (L)-isomer	MeSH, HMDB
L-3-Cyanoalanine	KEGG, ChEBI
(2S)-2-Amino-3-cyanopropanoic acid	HMDB
(2S)-2-Amino-3-cyanopropionic acid	HMDB
2-Amino-3-cyanopropanoic acid	HMDB
2-Amino-3-cyanopropionic acid	HMDB
3-Cyano-L-alanine	HMDB
L-2-Amino-3-cyanopropanoic acid	HMDB
L-2-Amino-3-cyanopropionic acid	HMDB
β-Cyano-L-alanine	HMDB
β-Cyanoalanine	HMDB

Chemical Formula

C₄H₆N₂O₂

Average Molecular Weight

114.1026

Monoisotopic Molecular Weight

114.042927446

IUPAC Name

(2S)-2-amino-3-cyanopropanoic acid

Traditional Name

3-cyanoalanine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1

InChI Key

BXRLWGXPSRYJDZ-VKHMYHEASA-N

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
Carbonitrile
Nitrile
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen 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:16934 )
cyanoamino acid (CHEBI:16934 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-3.4	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	0.23	ChemAxon
pKa (Strongest Basic)	7.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.11 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.51 m³·mol⁻¹	ChemAxon
Polarizability	10.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-2910000000-cdae81bdd716faf914cb	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0910000000-76fcf98a116d8f5fb3a3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-87a768329cbe7349b129	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9000000000-b588e4f0716ef2c3b6ea	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-9100000000-84aa6cdc91672d2d0c40	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9000000000-fe247d540e001b5b738b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0006-9000000000-0b174b16428577353612	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0udi-9000000000-b9d26a1c944b0649cadc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0002-9000000000-f17c4c09160c2e81931a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-c35c2982261090e1ac28	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-970b9d3c7c142d5bc7ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-1638709f55d082c64835	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-cc48714167e1ba803c7c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-0900000000-45c3feae2e1ceff7377d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-0900000000-bf090b5f90b37f228ec4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-1900000000-48b98dfc454b8b5ef5d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-2900000000-7490f45dd2e226996a58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-03di-4900000000-ba685d69c16b14e76f7f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-03dj-9800000000-9eb50c4dbae9090478e7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-01ot-9400000000-d239b0a8038ad871ad6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9200000000-1e9123df57023d142592	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9100000000-bee64b38054305fe23fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-36456509bbb17410a4c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-a9cd3d6dc542f1ebd0b3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-006t-9000000000-0923f4b6979f216eb757	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0002-9000000000-dc0d16ea8ae536cb82eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0udi-9000000000-e742d1778ed2916e7989	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-46983704961d3c708c40	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, positive	splash10-00di-9000000000-783db8104c08d8983467	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, positive	splash10-0a4j-8900000000-c3a0f4587b5f55cd8cf9	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer