MiMeDB: Showing metabocard for gamma-Glutamyl-beta-cyanoalanine (MMDBc0030063)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:52:31 UTC

Update Date

2022-08-31 17:39:25 UTC

Metabolite ID

MMDBc0030063

Metabolite Identification

Common Name

gamma-Glutamyl-beta-cyanoalanine

Description

Gamma-glutamyl-beta-cyanoalanine belongs to the class of 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 SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207012D          

 17 16  0  0  0  0            999 V2000
    3.3809    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.8395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 10  3  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
 12  6  1  4  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  2  0  0  0  0
  9 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030063

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CCC(O)=NC(CC#N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)

> <INCHI_KEY>
QUAADUAOVLZBJM-UHFFFAOYSA-N

> <FORMULA>
C9H13N3O5

> <MOLECULAR_WEIGHT>
243.2166

> <EXACT_MASS>
243.085520541

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
22.819512129208057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(1-carboxy-2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-3.14

> <JCHEM_LOGP>
-3.6080873277942107

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4242506375904784

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3562283540532833

> <JCHEM_PKA_STRONGEST_BASIC>
9.537515643281333

> <JCHEM_POLAR_SURFACE_AREA>
157

> <JCHEM_REFRACTIVITY>
54.121500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-glutamyl-β-cyanoalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.311   6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   8.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   9.034   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.310  -1.746   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.977   9.034   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.645  10.574   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.978   8.264   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3   10                                                       
CONECT    5    1    8   11                                                  
CONECT    6    3    9   12                                                  
CONECT    7    2   12   13                                                  
CONECT    8    5   14   15                                                  
CONECT    9    6   16   17                                                  
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6    7                                                       
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
g-Glutamyl-b-cyanoalanine	Generator
Γ-glutamyl-β-cyanoalanine	Generator

Molecular Formula

C₉H₁₃N₃O₅

Average Mass

243.2166

Monoisotopic Mass

243.085520541

IUPAC Name

2-amino-4-[(1-carboxy-2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

gamma-glutamyl-β-cyanoalanine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)

InChI Key

QUAADUAOVLZBJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Nitrile
Carbonitrile
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.96 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	157 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.12 m³·mol⁻¹	ChemAxon
Polarizability	22.82 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ta-1960000000-94e2babea849485ad37a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03yj-4910000000-a945ecde83676634e79d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07vi-9300000000-4a22b08b1e8ae019d558	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0590000000-e7012669ed04c13f2154	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00am-3940000000-7d5cabf0842228334ef5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-bdc2657f4628df6df454	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002645	L-Glutamic acid	gamma-Glutamyl-beta-cyanoalanine	gamma-glutamyltransferase 1		VMH; KEGG	30371894
MMDBr0007228	L-Glutamic acid	gamma-Glutamyl-beta-cyanoalanine	Not Available		VMH	30371894

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	135	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	61	Pig ; Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	18	Human feces; Human	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	6	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	9	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440768

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for gamma-Glutamyl-beta-cyanoalanine (MMDBc0030063)

MOL for #<Metabolite:0x00007fdb581dc668>

3D MOL for #<Metabolite:0x00007fdb581dc668>

3D SDF for #<Metabolite:0x00007fdb581dc668>

3D-SDF for #<Metabolite:0x00007fdb581dc668>

PDB for #<Metabolite:0x00007fdb581dc668>

3D PDB for #<Metabolite:0x00007fdb581dc668>

SMILES for #<Metabolite:0x00007fdb581dc668>

INCHI for #<Metabolite:0x00007fdb581dc668>

Structure for #<Metabolite:0x00007fdb581dc668>

3D Structure for #<Metabolite:0x00007fdb581dc668>