MiMeDB: Showing metabocard for 3-Cyano-L-alanine (MMDBc0029996)

Plant

Animal

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:49:57 UTC

Update Date

2024-04-30 19:43:57 UTC

Metabolite ID

MMDBc0029996

Metabolite Identification

Common Name

3-Cyano-L-alanine

Description

3-cyano-L-alanine is a member of the chemical class known as Alpha Amino Acids and Derivatives. 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Molecular Formula

C₄H₆N₂O₂

Average Mass

114.1026

Monoisotopic Mass

114.042927446

IUPAC Name

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

Traditional Name

3-cyanoalanine

CAS Registry Number

6232-19-5

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	31.3 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-2910000000-cdae81bdd716faf914cb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0910000000-76fcf98a116d8f5fb3a3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-87a768329cbe7349b129	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9000000000-b588e4f0716ef2c3b6ea	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-9100000000-84aa6cdc91672d2d0c40	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-9000000000-fe247d540e001b5b738b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0006-9000000000-0b174b16428577353612	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0udi-9000000000-b9d26a1c944b0649cadc	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0002-9000000000-f17c4c09160c2e81931a	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-c35c2982261090e1ac28	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-970b9d3c7c142d5bc7ba	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9000000000-1638709f55d082c64835	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-cc48714167e1ba803c7c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-0900000000-45c3feae2e1ceff7377d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-0900000000-bf090b5f90b37f228ec4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-1900000000-48b98dfc454b8b5ef5d4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-03di-2900000000-7490f45dd2e226996a58	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-03di-4900000000-ba685d69c16b14e76f7f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-03dj-9800000000-9eb50c4dbae9090478e7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-01ot-9400000000-d239b0a8038ad871ad6b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9200000000-1e9123df57023d142592	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0002-9100000000-bee64b38054305fe23fc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-36456509bbb17410a4c0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0002-9000000000-a9cd3d6dc542f1ebd0b3	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9200000000-0e19a40d51dba814046f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-9000000000-43854410a8c06907e442	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9000000000-f4e0d1a95b214a75ce61	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5900000000-b63ea9f293d3ea49c11b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-9300000000-f9254862ccdb5dd595af	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6b92c9baa9ac2b657576	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	500.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	360.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	37.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	232.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-23	279.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	351.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	466.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	803.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	830.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	214.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	456.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	233.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	53.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	400.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	669.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	78.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	301.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	666.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	587.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Cyano-L-alanine_TMS_1	C[Si](C)(C)OC(=O)[C@@H](N)CC#N	standard non polar	2025-10-23	1939.06
Gas Chromatography	3-Cyano-L-alanine_TMS_2	C[Si](C)(C)N[C@@H](CC#N)C(=O)O	standard non polar	2025-10-23	1772.47
Gas Chromatography	3-Cyano-L-alanine_TMS_3	C[Si](C)(C)N[C@@H](CC#N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1898.8
Gas Chromatography	3-Cyano-L-alanine_TMS_4	C[Si](C)(C)N([C@@H](CC#N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1685.05
Gas Chromatography	3-Cyano-L-alanine_TMS_5	C[Si](C)(C)OC(=O)[C@H](CC#N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1553.21
Gas Chromatography	3-Cyano-L-alanine_TMS_1	C[Si](C)(C)OC(=O)[C@@H](N)CC#N	standard polar	2025-10-23	2138.47
Gas Chromatography	3-Cyano-L-alanine_TMS_2	C[Si](C)(C)N[C@@H](CC#N)C(=O)O	standard polar	2025-10-23	2064.95
Gas Chromatography	3-Cyano-L-alanine_TMS_3	C[Si](C)(C)N[C@@H](CC#N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2060.95
Gas Chromatography	3-Cyano-L-alanine_TMS_4	C[Si](C)(C)N([C@@H](CC#N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2047.95
Gas Chromatography	3-Cyano-L-alanine_TMS_5	C[Si](C)(C)OC(=O)[C@H](CC#N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2072.82

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192366	Gamma-glutamyltranspeptidase 1	Enzyme	P19440	Homo sapiens
MMDBp0192367	Gamma-glutamyltransferase 7	Enzyme	Q9UJ14	Homo sapiens
MMDBp0194151	Gamma-glutamyltransferase 6	Enzyme	Q6P531	Homo sapiens
MMDBp0196022	Gamma-glutamyltransferase 5	Enzyme	P36269	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
L-glutamate metabolism II

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019184	L-Glutamic acid	gamma-Glutamyl-beta-cyanoalanine	Glutathione hydrolase proenzyme	Hydrolysis of bond	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	134	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	61	Pig ; Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	18	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	6	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	9	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060245

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439742

PDB ID

Not Available

ChEBI ID

16934

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for 3-Cyano-L-alanine (MMDBc0029996)

MOL for #<Metabolite:0x00007f9acf8ed8e0>

3D MOL for #<Metabolite:0x00007f9acf8ed8e0>

3D SDF for #<Metabolite:0x00007f9acf8ed8e0>

3D-SDF for #<Metabolite:0x00007f9acf8ed8e0>

PDB for #<Metabolite:0x00007f9acf8ed8e0>

3D PDB for #<Metabolite:0x00007f9acf8ed8e0>

SMILES for #<Metabolite:0x00007f9acf8ed8e0>

INCHI for #<Metabolite:0x00007f9acf8ed8e0>

Structure for #<Metabolite:0x00007f9acf8ed8e0>

3D Structure for #<Metabolite:0x00007f9acf8ed8e0>