NP-MRD: Showing NP-Card for gamma-Glutamyl-S-methylcysteine sulfoxide (NP0047337)

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Record Information

Version

2.0

Created at

2022-03-17 20:38:32 UTC

Updated at

2022-03-17 20:38:32 UTC

NP-MRD ID

NP0047337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamyl-S-methylcysteine sulfoxide

Description

Gamma-Glutamyl-S-methylcysteine sulfoxide belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Gamma-Glutamyl-S-methylcysteine sulfoxide is a very strong basic compound (based on its pKa). Outside of the human body, gamma-Glutamyl-S-methylcysteine sulfoxide has been detected, but not quantified in, a few different foods, such as garlics, onion-family vegetables, and soft-necked garlics. This could make gamma-glutamyl-S-methylcysteine sulfoxide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211092D          

 18 17  0  0  0  0            999 V2000
   -3.5733   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152   -0.4126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.0014    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -1.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047337

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O6S/c1-18(17)4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)

> <INCHI_KEY>
MQEBEBZYRKXMDL-UHFFFAOYSA-N

> <FORMULA>
C9H16N2O6S

> <MOLECULAR_WEIGHT>
280.298

> <EXACT_MASS>
280.072906944

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
26.353336979716207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(1-carboxy-2-methanesulfinylethyl)carbamoyl]butanoic acid

> <ALOGPS_LOGP>
-1.98

> <JCHEM_LOGP>
-5.608552325422516

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4465552621675877

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4139689270232725

> <JCHEM_PKA_STRONGEST_BASIC>
9.11204188801493

> <JCHEM_POLAR_SURFACE_AREA>
146.79

> <JCHEM_REFRACTIVITY>
62.67550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[(1-carboxy-2-methanesulfinylethyl)carbamoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -6.670  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -0.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.335  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -0.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       5.338  -0.003   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       1.335   2.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.003   2.311   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -4.003  -2.311   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -0.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.332  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.002  -0.003   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.002   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.670  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.338   1.538   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2                                                            
CONECT    4    5   15                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6   17   18                                                  
CONECT    8    9                                                            
CONECT    9    5    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    2   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15    4   14   16                                                  
CONECT   16   15                                                            
CONECT   17    7                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
g-Glutamyl-S-methylcysteine sulfoxide	Generator
g-Glutamyl-S-methylcysteine sulphoxide	Generator
gamma-Glutamyl-S-methylcysteine sulphoxide	Generator
Γ-glutamyl-S-methylcysteine sulfoxide	Generator
Γ-glutamyl-S-methylcysteine sulphoxide	Generator
2-Amino-4-[(1-carboxy-2-methanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoate	Generator
2-Amino-4-[(1-carboxy-2-methanesulphinylethyl)-C-hydroxycarbonimidoyl]butanoate	Generator
2-Amino-4-[(1-carboxy-2-methanesulphinylethyl)-C-hydroxycarbonimidoyl]butanoic acid	Generator

Chemical Formula

C₉H₁₆N₂O₆S

Average Mass

280.2980 Da

Monoisotopic Mass

280.07291 Da

IUPAC Name

2-amino-4-[(1-carboxy-2-methanesulfinylethyl)carbamoyl]butanoic acid

Traditional Name

2-amino-4-[(1-carboxy-2-methanesulfinylethyl)carbamoyl]butanoic acid

CAS Registry Number

1187-84-4

SMILES

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

InChI Identifier

InChI=1S/C9H16N2O6S/c1-18(17)4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)

InChI Key

MQEBEBZYRKXMDL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium cepa	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Sulfoxide
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Sulfinyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Amine
Primary amine
Organic oxide
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
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	ALOGPS
logP	-5.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.41	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.79 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	62.68 m³·mol⁻¹	ChemAxon
Polarizability	26.35 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

HMDB0031863

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008547

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

13894651

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Glutamyl-S-methylcysteine sulfoxide (NP0047337)

MOL for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

3D MOL for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

3D SDF for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

3D-SDF for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

PDB for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

3D PDB for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

SMILES for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

INCHI for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

Structure for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)

3D Structure for NP0047337 (gamma-Glutamyl-S-methylcysteine sulfoxide)