NP-MRD: Showing NP-Card for N-gamma-Glutamylcysteine (NP0334850)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 22:46:25 UTC

Updated at

2024-09-10 22:46:25 UTC

NP-MRD ID

NP0334850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-gamma-Glutamylcysteine

Description

N-gamma-Glutamylcysteine 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. N-gamma-Glutamylcysteine was first documented in 1993 (PMID: 8507655). Based on a literature review very few articles have been published on N-gamma-Glutamylcysteine.

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv2104 05262301182D          

 16 15  0  0  0  0            999 V2000
    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
   -2.3349    1.1270    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
   -1.6204    0.7145    0.0000 C   0  0  0  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
   -1.6204   -0.1105    0.0000 C   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
   -0.9059   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  2  6  1  0  0  0  0
  3  5  1  0  0  0  0
  3 16  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
 10  5  1  4  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  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
M  END
> <DATABASE_ID>
NP0334850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(O)=NC(CS)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)

> <INCHI_KEY>
RITKHVBHSGLULN-UHFFFAOYNA-N

> <FORMULA>
C8H14N2O5S

> <MOLECULAR_WEIGHT>
250.27

> <EXACT_MASS>
250.062342733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.723305221888637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-2.9484605093237297

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.8242487825773908

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9062706572764296

> <JCHEM_PKA_STRONGEST_BASIC>
9.42935411997359

> <JCHEM_POLAR_SURFACE_AREA>
133.21

> <JCHEM_REFRACTIVITY>
56.83310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.025  -0.206   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.691   2.104   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -0.357  -0.206   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.691  -0.976   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.358  -0.976   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0      -4.358   3.644   0.000  0.00  0.00           S+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    5   16                                                       
CONECT    4    1    7    9                                                  
CONECT    5    3    8   10                                                  
CONECT    6    2   10   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    5   14   15                                                  
CONECT    9    4                                                            
CONECT   10    5    6                                                       
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    3                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
N-g-Glutamylcysteine	Generator
N-Γ-glutamylcysteine	Generator

Chemical Formula

C₈H₁₄N₂O₅S

Average Mass

250.2700 Da

Monoisotopic Mass

250.06234 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(CCC(O)=NC(CS)C(O)=O)C(O)=O

InChI Identifier

InChI=1/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)

InChI Key

RITKHVBHSGLULN-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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 or derivatives
N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
N-acyl-amine
Fatty amide
Fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Alkylthiol
Carboxylic acid
Primary aliphatic amine
Organosulfur compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

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	-2.9	ChemAxon
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	133.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.83 m³·mol⁻¹	ChemAxon
Polarizability	23.72 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Γ-L-Glutamyl-L-cysteine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kinuta M, Ubuka T, Yao K, Yamada S, Yukihiro K, Tomozawa M: Preparation and characterization of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione and its derivatives as proposed precursors of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine, a compound found in human urine. Biochim Biophys Acta. 1993 Jun 11;1157(2):192-8. doi: 10.1016/0304-4165(93)90064-f. [PubMed:8507655 ]

Showing NP-Card for N-gamma-Glutamylcysteine (NP0334850)

MOL for NP0334850 (N-gamma-Glutamylcysteine)

3D MOL for NP0334850 (N-gamma-Glutamylcysteine)

3D SDF for NP0334850 (N-gamma-Glutamylcysteine)

3D-SDF for NP0334850 (N-gamma-Glutamylcysteine)

PDB for NP0334850 (N-gamma-Glutamylcysteine)

3D PDB for NP0334850 (N-gamma-Glutamylcysteine)

SMILES for NP0334850 (N-gamma-Glutamylcysteine)

INCHI for NP0334850 (N-gamma-Glutamylcysteine)

Structure for NP0334850 (N-gamma-Glutamylcysteine)

3D Structure for NP0334850 (N-gamma-Glutamylcysteine)