MiMeDB: Showing metabocard for gamma-Glutamyl-beta-aminopropiononitrile (MMDBc0030062)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:52:29 UTC

Update Date

2024-04-30 19:44:28 UTC

Metabolite ID

MMDBc0030062

Metabolite Identification

Common Name

gamma-Glutamyl-beta-aminopropiononitrile

Description

Gamma-glutamyl-beta-aminopropiononitrile 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


  Mrv0541 08131209302D          

 15 14  0  0  0  0            999 V2000
   -2.3349    1.1270    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
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    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
   -3.7638    0.3020    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
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    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
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  3  0  0  0  0
  6 10  1  1  0  0  0
 11  5  1  4  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
  6 15  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030062

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(O)=NCCC#N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13N3O3/c9-4-1-5-11-7(12)3-2-6(10)8(13)14/h6H,1-3,5,10H2,(H,11,12)(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
VQPVVWAFTIFKDD-LURJTMIESA-N

> <FORMULA>
C8H13N3O3

> <MOLECULAR_WEIGHT>
199.2071

> <EXACT_MASS>
199.095691297

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.084176651374424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-3.225940732736835

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.1862125812007696

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5023139462839143

> <JCHEM_PKA_STRONGEST_BASIC>
9.538122137864855

> <JCHEM_POLAR_SURFACE_AREA>
119.7

> <JCHEM_REFRACTIVITY>
48.2916

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4    5                                                       
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    1    9                                                       
CONECT    5    1   11                                                       
CONECT    6    2    8   10   15                                             
CONECT    7    3   11   12                                                  
CONECT    8    6   13   14                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    5    7                                                       
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0060477
HETATM    1  N1  UNL     1       2.486   2.055   1.948  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.086   1.313   1.277  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.852   0.394   0.457  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.968  -0.157  -0.669  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.851  -0.846  -0.074  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.682  -0.338   0.136  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.514   0.972  -0.250  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.349  -1.175   0.753  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.537  -1.508  -0.051  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.401  -0.418  -0.548  1.00  0.00           C  
HETATM   11  N3  UNL     1      -1.813   0.547  -1.411  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.157   0.273   0.525  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.752  -0.386   1.391  1.00  0.00           O  
HETATM   14  O3  UNL     1      -3.197   1.645   0.555  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.684   0.953  -0.015  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.252  -0.437   1.057  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.575  -0.850  -1.315  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.656   0.661  -1.317  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.807   1.415  -1.082  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.132  -2.162   1.025  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.637  -0.774   1.778  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.208  -2.213  -0.865  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.192  -2.161   0.602  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.210  -0.926  -1.168  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.026   0.383  -2.433  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.022   1.537  -1.153  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.045   2.203   0.519  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   19
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   12   24
CONECT   11   25   26
CONECT   12   13   13   14
CONECT   14   27
END

Synonyms

Value	Source
gamma-Glutamyl-3-aminopropiononitrile	ChEBI
g-Glutamyl-3-aminopropiononitrile	Generator
Γ-glutamyl-3-aminopropiononitrile	Generator
g-Glutamyl-b-aminopropiononitrile	Generator
Γ-glutamyl-β-aminopropiononitrile	Generator

Molecular Formula

C₈H₁₃N₃O₃

Average Mass

199.2071

Monoisotopic Mass

199.095691297

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCC(O)=NCCC#N)C(O)=O

InChI Identifier

InChI=1S/C8H13N3O3/c9-4-1-5-11-7(12)3-2-6(10)8(13)14/h6H,1-3,5,10H2,(H,11,12)(H,13,14)/t6-/m0/s1

InChI Key

VQPVVWAFTIFKDD-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:28092 )
L-glutamine derivative (CHEBI:28092 )
aliphatic nitrile (CHEBI:28092 )
carboxamide (CHEBI:28092 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.8 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.5	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.29 m³·mol⁻¹	ChemAxon
Polarizability	20.08 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 (Non-derivatized) - 70eV, Positive	splash10-0uec-9200000000-f218d4c91166ca03ce38	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-4290000000-3a1d60db995aff45ffa3	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-9810000000-a233576842f26de13176	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-9200000000-a6db4bf10b3c15dfd50f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-9000000000-917dcb7053cf2f990749	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-9d0a6c69667f7d6a86fd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00l2-4900000000-e2cc039bb0175e6b7161	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-cc0e7eb8ba343b858c49	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4590000000-0a447d1b6cfc6063f94b	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9400000000-c22ed552944f5df105f1	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-9000000000-97712e263528b7044832	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-496e5c0ed03ca00229a5	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ur-9700000000-d3f6caee9c201874729a	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9200000000-b077f442c50f547f7366	2021-10-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	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
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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002646	L-Glutamic acid	gamma-Glutamyl-beta-aminopropiononitrile	gamma-glutamyltransferase 1		VMH	1968061
MMDBr0007229	L-Glutamic acid	gamma-Glutamyl-beta-aminopropiononitrile	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

Source Type	Source Sub-type	Species	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

HMDB0060477

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389750

KEGG Compound ID

C06114

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440920

PDB ID

Not Available

ChEBI ID

28092

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Showing metabocard for gamma-Glutamyl-beta-aminopropiononitrile (MMDBc0030062)

MOL for #<Metabolite:0x00007fecfc63d9b8>

3D MOL for #<Metabolite:0x00007fecfc63d9b8>

3D SDF for #<Metabolite:0x00007fecfc63d9b8>

3D-SDF for #<Metabolite:0x00007fecfc63d9b8>

PDB for #<Metabolite:0x00007fecfc63d9b8>

3D PDB for #<Metabolite:0x00007fecfc63d9b8>

SMILES for #<Metabolite:0x00007fecfc63d9b8>

INCHI for #<Metabolite:0x00007fecfc63d9b8>

Structure for #<Metabolite:0x00007fecfc63d9b8>

3D Structure for #<Metabolite:0x00007fecfc63d9b8>