NP-MRD: Showing NP-Card for Malvidin 3-(6''-p-caffeyglucoside) (NP0045658)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:33:32 UTC

Updated at

2022-03-17 19:33:32 UTC

NP-MRD ID

NP0045658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Malvidin 3-(6''-p-caffeyglucoside)

Description

Malvidin 3-(6''-p-caffeyglucoside) 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. Malvidin 3-(6''-p-caffeyglucoside) is an extremely weak basic (essentially neutral) compound (based on its pKa). Malvidin 3-(6''-p-caffeyglucoside) may be a unique S. Malvidin 3-(6''-p-caffeyglucoside) is found in Orobanche minor and Vitis cinerea. Cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241212252D          

 47 51  0  0  0  0            999 V2000
   -4.6848    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559    1.4438    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -3.2559   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1138    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -2.2687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8269   -2.6813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1125   -2.2688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1125   -1.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8270   -1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8270   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1434   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7309   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1434   -5.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -5.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2059   -4.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9059   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4934   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -4.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  9 30  1  0  0  0  0
  4 20  1  0  0  0  0
  2 21  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 32  1  1  0  0  0
 27 26  1  0  0  0  0
 26 33  1  6  0  0  0
 27 28  1  0  0  0  0
 27 34  1  1  0  0  0
 28 29  1  0  0  0  0
 28 31  1  6  0  0  0
 29 30  1  1  0  0  0
 32 46  1  0  0  0  0
 35 36  2  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 41  1  0  0  0  0
 36 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
M  CHG  1   7   1
M  END

  Mrv0541 02241212252D          

 47 51  0  0  0  0            999 V2000
   -4.6848    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3993    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559    1.4438    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -3.2559   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1138    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -2.2687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8269   -2.6813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1125   -2.2688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1125   -1.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8270   -1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8270   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1434   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7309   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1434   -5.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -5.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2059   -4.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3809   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9059   -4.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4934   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -4.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  9 30  1  0  0  0  0
  4 20  1  0  0  0  0
  2 21  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 25 32  1  1  0  0  0
 27 26  1  0  0  0  0
 26 33  1  6  0  0  0
 27 28  1  0  0  0  0
 27 34  1  1  0  0  0
 28 29  1  0  0  0  0
 28 31  1  6  0  0  0
 29 30  1  1  0  0  0
 32 46  1  0  0  0  0
 35 36  2  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 41  1  0  0  0  0
 36 42  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0045658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=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(O)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32-/m1/s1

> <INCHI_KEY>
LIEHUFTYLLDHTI-KWNZYCHBSA-O

> <FORMULA>
C32H31O15

> <MOLECULAR_WEIGHT>
655.5795

> <EXACT_MASS>
655.166295322

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
64.97854707427916

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <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)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.2952999999999983

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.414881718998318

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.382279734884168

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64911035489539

> <JCHEM_POLAR_SURFACE_AREA>
238.19999999999996

> <JCHEM_REFRACTIVITY>
170.7325

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

> <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      -8.745   2.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.079   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.079   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.745  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.411   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.411   1.925   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.078   2.695   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0      -6.078  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.744   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.744   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.410   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.077   5.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.410   4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.077   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.743   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.743   4.235   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.077   6.545   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.591   5.005   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.591   1.925   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.745  -1.925   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -11.412   2.695   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.410   7.315   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.591   0.385   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.744  -2.695   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.744  -4.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.410  -5.005   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.077  -4.235   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.077  -2.695   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.410  -1.925   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.410  -0.385   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.743  -1.925   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.078  -5.005   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.410  -6.545   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.743  -5.005   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -13.778  -9.212   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -13.008  -7.879   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -11.468  -7.879   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -10.698  -9.212   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -11.468 -10.546   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -13.008 -10.546   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -15.318  -9.212   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -13.778  -6.545   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -9.158  -9.212   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.388  -7.879   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.848  -7.879   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.078  -6.545   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -6.078  -9.212   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   17                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   12   15   18                                                  
CONECT   17   12   22                                                       
CONECT   18   16                                                            
CONECT   19   15   23                                                       
CONECT   20    4                                                            
CONECT   21    2                                                            
CONECT   22   17                                                            
CONECT   23   19                                                            
CONECT   24   25   29                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   31                                                  
CONECT   29   24   28   30                                                  
CONECT   30    9   29                                                       
CONECT   31   28                                                            
CONECT   32   25   46                                                       
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   36   40   41                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   35   39                                                       
CONECT   41   35                                                            
CONECT   42   36                                                            
CONECT   43   38   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   32   45                                                       
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₁O₁₅

Average Mass

655.5795 Da

Monoisotopic Mass

655.16630 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

129016-23-5

SMILES

COC1=CC(=CC(OC)=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(O)=CC(O)=C2

InChI Identifier

InChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32-/m1/s1

InChI Key

LIEHUFTYLLDHTI-KWNZYCHBSA-O

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
Orobanche minor	Plant	KNApSAcK
Vitis cinerea	Plant	KNApSAcK
Vitis vinifera L.	FooDB	KNAPSACK

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Benzopyran
1-benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Styrene
Catechol
Methoxybenzene
Anisole
Fatty acid ester
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.31	ALOGPS
logP	3.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	238.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	170.73 m³·mol⁻¹	ChemAxon
Polarizability	64.98 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001594

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

11239215

PDB ID

Not Available

ChEBI ID

131452

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Malvidin 3-(6''-p-caffeyglucoside) (NP0045658)

MOL for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

3D MOL for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

3D SDF for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

3D-SDF for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

PDB for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

3D PDB for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

SMILES for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

INCHI for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

Structure for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))

3D Structure for NP0045658 (Malvidin 3-(6''-p-caffeyglucoside))