NP-MRD: Showing NP-Card for Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside] (NP0057875)

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Record Information

Version

2.0

Created at

2022-04-28 03:14:49 UTC

Updated at

2022-04-28 03:14:49 UTC

NP-MRD ID

NP0057875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside]

Description

2-(3,4-Dihydroxyphenyl)-3-{[(2S,3R,4S,5S,6S)-6-({[(2E)-3-(4-{[(2S,3R,4S,5S,6S)-6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium 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. Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside] is found in Ipomoea purpurea . Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-3-{[(2S,3R,4S,5S,6S)-6-({[(2E)-3-(4-{[(2S,3R,4S,5S,6S)-6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205142D          

112122  0  0  1  0            999 V2000
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103112  1  6  0  0  0
M  CHG  1   8   1
M  END

     RDKit          3D

191201  0  0  0  0  0  0  0  0999 V2000
   -3.9776    0.7183    2.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2400    0.6740    2.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  1  54   1
M  END


  Mrv1652304282205142D          

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104111  1  1  0  0  0
103112  1  6  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0057875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(\C=C\C(=O)OC[C@H]3O[C@@H](O[C@@H]4[C@@H](O)[C@H](O)[C@H](COC(=O)\C=C\C5=CC=C(O[C@@H]6O[C@@H](COC(=O)\C=C\C7=CC(O)=C(O)C=C7)[C@@H](O)[C@H](O)[C@H]6O)C(O)=C5)O[C@H]4OC4=CC5=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C=C(O)C=C5[O+]=C4C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]3O)=CC=C2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C72H78O40/c73-22-44-52(85)57(90)62(95)69(107-44)104-41-20-31(75)19-40-32(41)21-43(66(102-40)30-7-10-34(77)37(80)18-30)106-72-67(112-71-65(98)60(93)55(88)47(110-71)25-100-51(84)14-6-29-2-9-35(78)42(17-29)105-70-63(96)58(91)53(86)45(23-74)108-70)61(94)56(89)48(111-72)26-101-50(83)13-5-28-3-11-39(38(81)16-28)103-68-64(97)59(92)54(87)46(109-68)24-99-49(82)12-4-27-1-8-33(76)36(79)15-27/h1-21,44-48,52-65,67-74,85-98H,22-26H2,(H6-,75,76,77,78,79,80,81,82,84)/p+1/b13-5+/t44-,45-,46+,47-,48+,52-,53-,54-,55-,56-,57+,58+,59+,60+,61+,62-,63-,64-,65-,67-,68-,69-,70-,71+,72-/m1/s1

> <INCHI_KEY>
GCCDPPQEZBMKPT-RTWFMPGVSA-O

> <FORMULA>
C72H79O40

> <MOLECULAR_WEIGHT>
1584.383

> <EXACT_MASS>
1583.414213764

> <JCHEM_ACCEPTOR_COUNT>
37

> <JCHEM_ATOM_COUNT>
191

> <JCHEM_AVERAGE_POLARIZABILITY>
150.4334488730753

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
23

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
-0.3316999999999979

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.951834019076299

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.6462143975084675

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9541359824103965

> <JCHEM_POLAR_SURFACE_AREA>
649.6300000000003

> <JCHEM_REFRACTIVITY>
375.69249999999977

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.45e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+1
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.000 -18.480   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334 -20.790   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.001 -23.870   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667 -26.180   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.669 -27.720   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.336 -28.490   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      12.003 -28.490   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      12.003 -25.410   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      18.672 -13.860   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      22.673 -19.250   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0      24.006 -16.940   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      24.006 -13.860   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   99  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM  102  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM  107  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM  108  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM  109  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2    6  101                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   93                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    2                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   58                                                  
CONECT   15   14   16   57                                                  
CONECT   16   15   17   56                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29                                                            
CONECT   32   28   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35   55                                                  
CONECT   35   34   36   54                                                  
CONECT   36   35   37   53                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37   33                                                       
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49   45                                                       
CONECT   51   48                                                            
CONECT   52   47                                                            
CONECT   53   36                                                            
CONECT   54   35                                                            
CONECT   55   34                                                            
CONECT   56   16                                                            
CONECT   57   15                                                            
CONECT   58   14   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   59   61   92                                                  
CONECT   61   60   62   91                                                  
CONECT   62   61   63   90                                                  
CONECT   63   62   64   65                                                  
CONECT   64   63   59                                                       
CONECT   65   63   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72   76                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75   89                                                  
CONECT   75   74   76   77                                                  
CONECT   76   75   71                                                       
CONECT   77   75   78                                                       
CONECT   78   77   79   83                                                  
CONECT   79   78   80   88                                                  
CONECT   80   79   81   87                                                  
CONECT   81   80   82   86                                                  
CONECT   82   81   83   84                                                  
CONECT   83   82   78                                                       
CONECT   84   82   85                                                       
CONECT   85   84                                                            
CONECT   86   81                                                            
CONECT   87   80                                                            
CONECT   88   79                                                            
CONECT   89   74                                                            
CONECT   90   62                                                            
CONECT   91   61                                                            
CONECT   92   60                                                            
CONECT   93    9   94   98                                                  
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97  100                                                  
CONECT   97   96   98   99                                                  
CONECT   98   97   93                                                       
CONECT   99   97                                                            
CONECT  100   96                                                            
CONECT  101    1  102                                                       
CONECT  102  101  103  107                                                  
CONECT  103  102  104  112                                                  
CONECT  104  103  105  111                                                  
CONECT  105  104  106  110                                                  
CONECT  106  105  107  108                                                  
CONECT  107  106  102                                                       
CONECT  108  106  109                                                       
CONECT  109  108                                                            
CONECT  110  105                                                            
CONECT  111  104                                                            
CONECT  112  103                                                            
MASTER        0    0    0    0    0    0    0    0  112    0  244    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇₂H₇₉O₄₀

Average Mass

1584.3830 Da

Monoisotopic Mass

1583.41421 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(\C=C\C(=O)OC[C@H]3O[C@@H](O[C@@H]4[C@@H](O)[C@H](O)[C@H](COC(=O)\C=C\C5=CC=C(O[C@@H]6O[C@@H](COC(=O)\C=C\C7=CC(O)=C(O)C=C7)[C@@H](O)[C@H](O)[C@H]6O)C(O)=C5)O[C@H]4OC4=CC5=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C=C(O)C=C5[O+]=C4C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]3O)=CC=C2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C72H78O40/c73-22-44-52(85)57(90)62(95)69(107-44)104-41-20-31(75)19-40-32(41)21-43(66(102-40)30-7-10-34(77)37(80)18-30)106-72-67(112-71-65(98)60(93)55(88)47(110-71)25-100-51(84)14-6-29-2-9-35(78)42(17-29)105-70-63(96)58(91)53(86)45(23-74)108-70)61(94)56(89)48(111-72)26-101-50(83)13-5-28-3-11-39(38(81)16-28)103-68-64(97)59(92)54(87)46(109-68)24-99-49(82)12-4-27-1-8-33(76)36(79)15-27/h1-21,44-48,52-65,67-74,85-98H,22-26H2,(H6-,75,76,77,78,79,80,81,82,84)/p+1/b13-5+/t44-,45-,46+,47-,48+,52-,53-,54-,55-,56-,57+,58+,59+,60+,61+,62-,63-,64-,65-,67-,68-,69-,70-,71+,72-/m1/s1

InChI Key

GCCDPPQEZBMKPT-RTWFMPGVSA-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
Ipomoea purpurea	Plant	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-5-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
7-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
1-benzopyran
Benzopyran
Tricarboxylic acid or derivatives
Phenoxy compound
Styrene
Phenol ether
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	2.23	ALOGPS
logP	-0.33	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.65	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	37	ChemAxon
Hydrogen Donor Count	23	ChemAxon
Polar Surface Area	649.63 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	375.69 m³·mol⁻¹	ChemAxon
Polarizability	150.43 Å³	ChemAxon
Number of Rings	11	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

Not Available

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

163192158

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside] (NP0057875)

MOL for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

3D MOL for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

3D SDF for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

3D-SDF for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

PDB for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

3D PDB for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

SMILES for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

INCHI for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

Structure for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])

3D Structure for NP0057875 (Cyanidin 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-caffeyl)-beta-D-glucopyranposyl)caffeyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside])