NP-MRD: Showing NP-Card for L-gamma-Glutamyl-S-allylthio-L-cysteine (NP0049151)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:55 UTC

Updated at

2022-03-17 21:07:55 UTC

NP-MRD ID

NP0049151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-gamma-Glutamyl-S-allylthio-L-cysteine

Description

L-gamma-Glutamyl-S-allylthio-L-cysteine 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. L-gamma-Glutamyl-S-allylthio-L-cysteine is a very strong basic compound (based on its pKa). Outside of the human body, L-gamma-Glutamyl-S-allylthio-L-cysteine has been detected, but not quantified in, a few different foods, such as garlics, onion-family vegetables, and soft-necked garlics. This could make L-gamma-glutamyl-S-allylthio-L-cysteine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209052D          

 20 19  0  0  0  0            999 V2000
   -2.2259   -1.5662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -1.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279    0.1649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    0.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420    0.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9064    0.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4839    1.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645    1.5662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4013   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    0.0830    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -0.2467    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5453    0.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279    0.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049151

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O5S2/c1-2-5-19-20-6-8(11(17)18)13-9(14)4-3-7(12)10(15)16/h2,7-8H,1,3-6,12H2,(H,13,14)(H,15,16)(H,17,18)

> <INCHI_KEY>
VTEHWEWRSAXLHY-UHFFFAOYSA-N

> <FORMULA>
C11H18N2O5S2

> <MOLECULAR_WEIGHT>
322.401

> <EXACT_MASS>
322.065713076

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.603491332858955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.20

> <JCHEM_LOGP>
-2.538329545792439

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.7891111255692627

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7098861665699223

> <JCHEM_PKA_STRONGEST_BASIC>
9.312043531435169

> <JCHEM_POLAR_SURFACE_AREA>
129.71999999999997

> <JCHEM_REFRACTIVITY>
78.2322

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]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      -4.155  -2.924   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.387  -2.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.772  -2.769   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -6.772   0.308   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -5.387  -0.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   0.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.770  -0.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.385   0.155   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.692   1.693   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.770   2.617   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.385   1.847   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.307   2.924   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       0.000  -0.461   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.231   0.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.616  -0.461   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       4.001   0.155   0.000  0.00  0.00           S+0
HETATM   17  S   UNK     0       5.233  -0.461   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0       6.618   0.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.772   1.847   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.541   2.617   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    2    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   11   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
L-g-Glutamyl-S-allylthio-L-cysteine	Generator
L-Γ-glutamyl-S-allylthio-L-cysteine	Generator
2-Amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoate	Generator
2-Amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulphanyl)ethyl]-C-hydroxycarbonimidoyl}butanoate	Generator
2-Amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulphanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid	Generator

Chemical Formula

C₁₁H₁₈N₂O₅S₂

Average Mass

322.4010 Da

Monoisotopic Mass

322.06571 Da

IUPAC Name

2-amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]carbamoyl}butanoic acid

Traditional Name

2-amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCC(=O)NC(CSSCC=C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H18N2O5S2/c1-2-5-19-20-6-8(11(17)18)13-9(14)4-3-7(12)10(15)16/h2,7-8H,1,3-6,12H2,(H,13,14)(H,15,16)(H,17,18)

InChI Key

VTEHWEWRSAXLHY-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 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
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Amino acid or derivatives
Carboxamide group
Allyl sulfur compound
Amino acid
Dialkyldisulfide
Organic disulfide
Secondary carboxylic acid amide
Carboxylic acid
Sulfenyl compound
Hydrocarbon derivative
Amine
Primary aliphatic amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Organic nitrogen 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	-2.2	ALOGPS
logP	-2.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	78.23 m³·mol⁻¹	ChemAxon
Polarizability	31.6 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

HMDB0038515

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017895

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

131752387

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for L-gamma-Glutamyl-S-allylthio-L-cysteine (NP0049151)

MOL for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

3D MOL for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

3D SDF for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

3D-SDF for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

PDB for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

3D PDB for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

SMILES for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

INCHI for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

Structure for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)

3D Structure for NP0049151 (L-gamma-Glutamyl-S-allylthio-L-cysteine)