Np mrd loader

Showing NP-Card for Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside (NP0339450)

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Record Information
Version2.0
Created at2024-09-11 21:55:09 UTC
Updated at2024-09-11 21:55:09 UTC
NP-MRD IDNP0339450
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside
DescriptionCyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Based on a literature review very few articles have been published on Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)


  Mrv2104 05272300272D          

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M  CHG  1   7   1
M  END
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3D MOL for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)

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3D SDF for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)

  Mrv2104 05272300272D          

 67 73  0  0  0  0            999 V2000
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 57 62  1  0  0  0  0
 58 59  1  0  0  0  0
 58 66  1  1  0  0  0
 59 60  1  0  0  0  0
 59 65  1  6  0  0  0
 60 61  1  0  0  0  0
 60 64  1  1  0  0  0
 61 62  1  0  0  0  0
 61 63  1  6  0  0  0
 66 67  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0339450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(67-42-38(58)35(55)32(52)28(14-45)65-42)36(56)33(53)29(66-43)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/s2

> <INCHI_KEY>
DGVPBUDMTNUREK-JUDRWYBTNA-O

> <FORMULA>
C43H49O24

> <MOLECULAR_WEIGHT>
949.84

> <EXACT_MASS>
949.260828878

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
92.03546568876739

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

> <JCHEM_LOGP>
-1.2320000000000046

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.337462642396366

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.660263280227702

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678946886908562

> <JCHEM_POLAR_SURFACE_AREA>
387.2700000000001

> <JCHEM_REFRACTIVITY>
228.82700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)
Download
PDB for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.080   2.805   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.414   2.035   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.414   0.495   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080  -0.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.746   0.495   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.746   2.035   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.413   2.805   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0      -0.413  -0.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.921   0.495   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.921   2.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.255   2.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.588   5.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.255   4.345   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.588   2.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.922   2.805   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.922   4.345   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.747   2.805   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.080  -1.815   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.255  -0.275   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.256   5.115   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.256   2.035   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.921  -2.585   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.921  -4.125   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.255  -4.895   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.588  -4.125   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.588  -2.585   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.255  -1.815   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.922  -1.815   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.922  -4.895   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.255  -6.435   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.413  -4.895   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.413  -6.435   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.589   2.805   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.747  -1.815   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.081  -2.585   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.081  -4.125   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.747  -4.895   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.414  -4.125   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.414  -2.585   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.080  -4.895   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.747  -6.435   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -8.415  -4.895   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -8.415  -1.815   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -9.748  -2.585   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -3.080 -11.055   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.414 -11.825   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.414 -13.365   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.080 -14.135   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -1.746 -13.365   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.746 -11.825   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -3.080  -9.515   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.746  -8.745   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -1.746  -7.205   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -3.080  -6.435   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -3.080 -15.675   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -5.747 -14.135   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       6.256  -4.125   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       7.589  -4.895   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       8.923  -4.125   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.923  -2.585   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       7.589  -1.815   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       6.256  -2.585   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       7.589  -0.275   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      10.257  -1.815   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      10.257  -4.895   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       7.589  -6.435   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       8.923  -7.205   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   12   15   20                                                  
CONECT   17    2                                                            
CONECT   18    4   39                                                       
CONECT   19    9   27                                                       
CONECT   20   16                                                            
CONECT   21   15   33                                                       
CONECT   22   23   27                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   19   22   26                                                  
CONECT   28   26   62                                                       
CONECT   29   25                                                            
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31   53                                                       
CONECT   33   21                                                            
CONECT   34   35   39                                                       
CONECT   35   34   36   43                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   18   34   38                                                  
CONECT   40   38                                                            
CONECT   41   37                                                            
CONECT   42   36                                                            
CONECT   43   35   44                                                       
CONECT   44   43                                                            
CONECT   45   46   50   51                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   56                                                  
CONECT   48   47   49   55                                                  
CONECT   49   48   50                                                       
CONECT   50   49   45                                                       
CONECT   51   45   52                                                       
CONECT   52   51   53                                                       
CONECT   53   32   52   54                                                  
CONECT   54   53                                                            
CONECT   55   48                                                            
CONECT   56   47                                                            
CONECT   57   58   62                                                       
CONECT   58   57   59   66                                                  
CONECT   59   58   60   65                                                  
CONECT   60   59   61   64                                                  
CONECT   61   60   62   63                                                  
CONECT   62   28   57   61                                                  
CONECT   63   61                                                            
CONECT   64   60                                                            
CONECT   65   59                                                            
CONECT   66   58   67                                                       
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  146    0
END

Download
3D PDB for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)
Download
SMILES for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)
COC1=CC(=CC=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=CC(O)=C2
Download
INCHI for NP0339450 (Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside)
InChI=1/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(67-42-38(58)35(55)32(52)28(14-45)65-42)36(56)33(53)29(66-43)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC43H49O24
Average Mass949.8400 Da
Monoisotopic Mass949.26083 Da
IUPAC Name3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
Traditional Name3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=CC(O)=C2
InChI Identifier
InChI=1/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(67-42-38(58)35(55)32(52)28(14-45)65-42)36(56)33(53)29(66-43)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/s2
InChI KeyDGVPBUDMTNUREK-JUDRWYBTNA-O
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentAnthocyanidin 3-O-6-p-coumaroyl glycosides  
Alternative Parents
Substituents
  • Anthocyanidin 3-o-6-p-coumaroyl-glycoside
    • 

  • Anthocyanin
    • 

  • Anthocyanidin-5-o-glycoside
    • 

  • Anthocyanidin-3-o-glycoside
    • 

  • Flavonoid-3-o-glycoside
    • 

  • 3p-methoxyflavonoid-skeleton
    • 

  • 4'-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Anthocyanidin
    • 

  • Phenolic glycoside
    • 

  • Hydroxycinnamic acid or derivatives
    • 

  • Coumaric acid or derivatives
    • 

  • Cinnamic acid ester
    • 

  • Cinnamic acid or derivatives
    • 

  • O-glycosyl compound
    • 

  • Disaccharide
    • 

  • Glycosyl compound
    • 

  • Methoxyphenol
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Catechol
    • 

  • Phenol ether
    • 

  • Styrene
    • 

  • Fatty acid ester
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Fatty acyl
    • 

  • Oxane
    • 

  • Monocyclic benzene moiety
    • 

  • Heteroaromatic compound
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Ether
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organic cation
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ChemAxon
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area387.27 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity228.83 m³·mol⁻¹ChemAxon
Polarizability92.04 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available