NP-MRD: Showing NP-Card for gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide (NP0047338)

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Record Information

Version

2.0

Created at

2022-03-17 20:38:33 UTC

Updated at

2022-03-17 20:38:33 UTC

NP-MRD ID

NP0047338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide

Description

Gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide 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. Gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide is a very strong basic compound (based on its pKa). Outside of the human body, gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide has been detected, but not quantified in, several different foods, such as allium (onion), garden onions, onion-family vegetables, and soft-necked garlics. This could make gamma-glutamyl-S-(1-propenyl)cysteine sulfoxide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210192D          

 20 19  0  0  0  0            999 V2000
   -4.2871   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.4126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -0.0014    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -1.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124    0.8252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    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 20  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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047338

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O6S/c1-2-5-20(19)6-8(11(17)18)13-9(14)4-3-7(12)10(15)16/h2,5,7-8H,3-4,6,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)/b5-2+

> <INCHI_KEY>
LMNDKWXDMBGGAL-GORDUTHDSA-N

> <FORMULA>
C11H18N2O6S

> <MOLECULAR_WEIGHT>
306.335

> <EXACT_MASS>
306.088557008

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.67880219125223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-4.508194583575427

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.563471274140791

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4524948172809977

> <JCHEM_PKA_STRONGEST_BASIC>
9.112052972296548

> <JCHEM_POLAR_SURFACE_AREA>
146.79

> <JCHEM_REFRACTIVITY>
72.0512

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulfinyl]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      -8.003  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.668  -0.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.668   1.540   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       0.002  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.335  -0.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.670  -0.770   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       4.005  -0.003   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       0.002   2.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.670   2.311   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -5.335  -2.311   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.000  -0.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.665  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.330  -0.003   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.330   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.338  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.670  -0.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.003  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.005   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   20                                                  
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   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    7                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
g-Glutamyl-S-(1-propenyl)cysteine sulfoxide	Generator
g-Glutamyl-S-(1-propenyl)cysteine sulphoxide	Generator
gamma-Glutamyl-S-(1-propenyl)cysteine sulphoxide	Generator
Γ-glutamyl-S-(1-propenyl)cysteine sulfoxide	Generator
Γ-glutamyl-S-(1-propenyl)cysteine sulphoxide	Generator
2-Amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulfinyl]ethyl}-C-hydroxycarbonimidoyl)butanoate	Generator
2-Amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulphinyl]ethyl}-C-hydroxycarbonimidoyl)butanoate	Generator
2-Amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulphinyl]ethyl}-C-hydroxycarbonimidoyl)butanoic acid	Generator

Chemical Formula

C₁₁H₁₈N₂O₆S

Average Mass

306.3350 Da

Monoisotopic Mass

306.08856 Da

IUPAC Name

2-amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulfinyl]ethyl}carbamoyl)butanoic acid

Traditional Name

2-amino-4-({1-carboxy-2-[(1E)-prop-1-ene-1-sulfinyl]ethyl}carbamoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

C\C=C\S(=O)CC(NC(=O)CCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H18N2O6S/c1-2-5-20(19)6-8(11(17)18)13-9(14)4-3-7(12)10(15)16/h2,5,7-8H,3-4,6,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)/b5-2+

InChI Key

LMNDKWXDMBGGAL-GORDUTHDSA-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
Alpha-amino acid
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acyl
Fatty amide
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Sulfoxide
Secondary carboxylic acid amide
Carboxylic acid
Sulfinyl compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen 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	-1.6	ALOGPS
logP	-4.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.45	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	9	ChemAxon
Refractivity	72.05 m³·mol⁻¹	ChemAxon
Polarizability	29.68 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

HMDB0031870

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008555

KNApSAcK ID

Not Available

Chemspider ID

13392987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18410556

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-(1-propenyl)cysteine sulfoxide (NP0047338)

MOL for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

3D MOL for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

3D SDF for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

3D-SDF for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

PDB for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

3D PDB for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

SMILES for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

INCHI for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

Structure for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)

3D Structure for NP0047338 (gamma-Glutamyl-S-(1-propenyl)cysteine sulfoxide)