NP-MRD: Showing NP-Card for 2-S-Glutathionyl caftaric acid (NP0045285)

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Record Information

Version

2.0

Created at

2022-03-17 19:17:16 UTC

Updated at

2022-03-17 19:17:16 UTC

NP-MRD ID

NP0045285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-S-Glutathionyl caftaric acid

Description

2-S-Glutathionyl caftaric acid is found in Vitis vinifera.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212082D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241212082D          

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  1  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  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
 12 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  2  0  0  0  0
 37 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(=O)NC(CSC1=C(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)C=CC(O)=C1O)C(=O)NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H27N3O15S/c24-10(21(35)36)3-5-13(28)26-11(20(34)25-7-14(29)30)8-42-19-9(1-4-12(27)16(19)32)2-6-15(31)41-18(23(39)40)17(33)22(37)38/h1-2,4,6,10-11,17-18,27,32-33H,3,5,7-8,24H2,(H,25,34)(H,26,28)(H,29,30)(H,35,36)(H,37,38)(H,39,40)/b6-2+

> <INCHI_KEY>
FRUUTAANUZUTPG-QHHAFSJGSA-N

> <FORMULA>
C23H27N3O15S

> <MOLECULAR_WEIGHT>
617.537

> <EXACT_MASS>
617.116287899

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
56.59944700933338

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-4.588113278089005

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.7061900423891254

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6684928784401194

> <JCHEM_PKA_STRONGEST_BASIC>
8.919995650342186

> <JCHEM_POLAR_SURFACE_AREA>
320.40999999999997

> <JCHEM_REFRACTIVITY>
137.376

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic 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  C   UNK     0       0.550  -2.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.220  -0.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.760  -0.866   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.530  -2.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.760  -3.534   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.220  -3.534   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.550   0.467   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.090  -2.200   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0      -2.530   0.467   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0      -4.070  -2.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.840  -3.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.380  -3.534   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.150  -4.867   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.690  -4.867   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.150  -2.200   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -9.460  -6.201   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -11.000  -6.201   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.690  -7.535   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.460  -3.534   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.690  -2.200   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -11.000  -3.534   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -11.770  -2.200   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -11.770  -4.867   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.070   0.467   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.840   1.801   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.380   1.801   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -7.150   3.135   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -8.690   3.135   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.460   4.468   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.150   0.467   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -11.000   4.468   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.690   5.802   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0      -4.070   3.135   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      -2.530   3.135   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.760   4.468   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.220   4.468   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.550   5.802   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       2.090   5.802   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0      -1.760   1.801   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.220   7.136   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.760   7.136   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.550   8.469   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9    3   24                                                       
CONECT   10    4   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13   16   19                                                  
CONECT   15   12                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    9   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   31   32                                                  
CONECT   30   26                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   25   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37                                                            
CONECT   39   34                                                            
CONECT   40   37   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

View in JSmol

Synonyms

Value	Source
2-S-Glutathionyl caftarate	Generator

Chemical Formula

C₂₃H₂₇N₃O₁₅S

Average Mass

617.5370 Da

Monoisotopic Mass

617.11629 Da

IUPAC Name

2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

2-{[(2E)-3-(2-{[2-(4-amino-4-carboxybutanamido)-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

NC(CCC(=O)NC(CSC1=C(\C=C\C(=O)OC(C(O)C(O)=O)C(O)=O)C=CC(O)=C1O)C(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C23H27N3O15S/c24-10(21(35)36)3-5-13(28)26-11(20(34)25-7-14(29)30)8-42-19-9(1-4-12(27)16(19)32)2-6-15(31)41-18(23(39)40)17(33)22(37)38/h1-2,4,6,10-11,17-18,27,32-33H,3,5,7-8,24H2,(H,25,34)(H,26,28)(H,29,30)(H,35,36)(H,37,38)(H,39,40)/b6-2+

InChI Key

FRUUTAANUZUTPG-QHHAFSJGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	PHENOL EXPLORER

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Pentacarboxylic acid or derivatives
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cinnamic acid ester
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cysteine or derivatives
Coumaric acid or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Aryl thioether
Thiophenol ether
Catechol
Styrene
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
1-hydroxy-4-unsubstituted benzenoid
Alkylarylthioether
Fatty acid ester
Alpha-hydroxy acid
Fatty amide
Fatty acyl
Hydroxy acid
Benzenoid
Monosaccharide
N-acyl-amine
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Amino acid
Carboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Sulfenyl compound
Thioether
Carboxylic acid
Organooxygen compound
Organosulfur compound
Carbonyl group
Primary amine
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	-1.1	ALOGPS
logP	-4.6	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.67	ChemAxon
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	320.41 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	137.38 m³·mol⁻¹	ChemAxon
Polarizability	56.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

FDB000246

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

117842555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-S-Glutathionyl caftaric acid (NP0045285)

MOL for NP0045285 (2-S-Glutathionyl caftaric acid)

3D MOL for NP0045285 (2-S-Glutathionyl caftaric acid)

3D SDF for NP0045285 (2-S-Glutathionyl caftaric acid)

3D-SDF for NP0045285 (2-S-Glutathionyl caftaric acid)

PDB for NP0045285 (2-S-Glutathionyl caftaric acid)

3D PDB for NP0045285 (2-S-Glutathionyl caftaric acid)

SMILES for NP0045285 (2-S-Glutathionyl caftaric acid)

INCHI for NP0045285 (2-S-Glutathionyl caftaric acid)

Structure for NP0045285 (2-S-Glutathionyl caftaric acid)

3D Structure for NP0045285 (2-S-Glutathionyl caftaric acid)