NP-MRD: Showing NP-Card for p-Coumaroyl vitisin A (NP0336477)

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Record Information

Version

2.0

Created at

2024-09-11 06:25:44 UTC

Updated at

2024-09-11 06:25:44 UTC

NP-MRD ID

NP0336477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

p-Coumaroyl vitisin A

Description

P-Coumaroyl vitisin A 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. p-Coumaroyl vitisin A was first documented in 2022 (PMID: 36046366). Based on a literature review very few articles have been published on p-Coumaroyl vitisin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262308572D          

 51 56  0  0  0  0            999 V2000
    2.0552    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    2.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    3.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    3.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    4.7814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    5.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262    3.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    3.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    2.7189    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -2.9461    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0895    2.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    0.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -0.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -1.1249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    1.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.9936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2316   -1.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -1.4061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8027   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.9936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6262   -1.4061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.1686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6262    0.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -6.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -4.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -3.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -2.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -7.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 14 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 21 28  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 50  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  6  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 42 51  1  0  0  0  0
M  CHG  1  13   1
M  END


  Mrv2104 05262308572D          

 51 56  0  0  0  0            999 V2000
    2.0552    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    2.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    3.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    3.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882    4.7814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    5.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262    3.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407    3.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    2.7189    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -2.9461    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    2.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751    2.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0895    2.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3751    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606    0.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9434   -0.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -1.1249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    1.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.9936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2316   -1.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -1.4061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8027   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.9936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6262   -1.4061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -0.1686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6262    0.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -6.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -5.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -4.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -3.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461   -2.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -7.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 14 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 21 28  2  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 50  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  6  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 42 51  1  0  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
NP0336477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1OC1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1/C35H30O16/c1-45-22-9-16(10-23(46-2)28(22)39)32-33(19-13-24(34(43)44)48-20-11-18(37)12-21(49-32)27(19)20)51-35-31(42)30(41)29(40)25(50-35)14-47-26(38)8-5-15-3-6-17(36)7-4-15/h3-13,25,29-31,35,40-42H,14H2,1-2H3,(H3-,36,37,38,39,43,44)/p+1/t25-,29-,30+,31-,35?/s2

> <INCHI_KEY>
GOINLVYYMYVHAQ-QTPJAHDVNA-O

> <FORMULA>
C35H31O16

> <MOLECULAR_WEIGHT>
707.616

> <EXACT_MASS>
707.160661338

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
68.38574158567434

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

> <JCHEM_LOGP>
3.8002999999999973

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.229287097485878

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.041571785871252

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491103591665754

> <JCHEM_POLAR_SURFACE_AREA>
244.26999999999995

> <JCHEM_REFRACTIVITY>
183.94189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       3.836   5.075   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.503   4.305   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.169   5.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.165   4.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.498   5.075   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.498   6.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.165   7.385   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.165   8.925   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.498   9.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.169   6.615   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.503   7.385   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.832   4.305   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.166   5.075   0.000  0.00  0.00           O+1
HETATM   14  C   UNK     0      -5.499   4.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.833   5.075   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.167   4.305   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.500   5.075   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.167   2.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.833   1.995   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.499   2.765   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.166   1.995   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.166   0.455   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.499  -0.315   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.833   0.455   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.494  -1.525   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.520  -2.100   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.578  -2.235   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.832   2.765   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.498   1.995   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.498   0.455   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.832  -0.315   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.832  -1.855   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.166  -2.625   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.498  -2.625   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.498  -4.165   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.165  -1.855   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.169  -2.625   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.165  -0.315   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.169   0.455   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -5.499  -9.555   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.499 -11.095   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.166 -11.865   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.832 -11.095   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.832  -9.555   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -4.166  -8.785   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.166  -7.245   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -5.499  -6.475   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -5.499  -4.935   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -6.833  -4.165   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -4.166  -4.165   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -4.166 -13.405   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21   12   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   50                                                       
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   30   39                                                  
CONECT   39   38                                                            
CONECT   40   41   45                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   51                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   33   48                                                       
CONECT   51   42                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₁O₁₆

Average Mass

707.6160 Da

Monoisotopic Mass

707.16066 Da

IUPAC Name

7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),2,4,6,9,11-hexaen-2-ylium

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1OC1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=CC(O)=C2

InChI Identifier

InChI=1/C35H30O16/c1-45-22-9-16(10-23(46-2)28(22)39)32-33(19-13-24(34(43)44)48-20-11-18(37)12-21(49-32)27(19)20)51-35-31(42)30(41)29(40)25(50-35)14-47-26(38)8-5-15-3-6-17(36)7-4-15/h3-13,25,29-31,35,40-42H,14H2,1-2H3,(H3-,36,37,38,39,43,44)/p+1/t25-,29-,30+,31-,35?/s2

InChI Key

GOINLVYYMYVHAQ-QTPJAHDVNA-O

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This 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.

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
Proanthocyanidin
Bi- and polyflavonoid skeleton
Anthocyanin
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Ether
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	3.8	ChemAxon
pKa (Strongest Acidic)	2.04	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	244.27 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	183.94 m³·mol⁻¹	ChemAxon
Polarizability	68.39 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Z, Wang L, Du M, Liang Y, Liang M, Li Z, Gao Y: Plasm Metabolomics Study in Pulmonary Metastatic Carcinoma. J Oncol. 2022 Aug 21;2022:9460019. doi: 10.1155/2022/9460019. eCollection 2022. [PubMed:36046366 ]

Showing NP-Card for p-Coumaroyl vitisin A (NP0336477)

MOL for NP0336477 (p-Coumaroyl vitisin A)

3D MOL for NP0336477 (p-Coumaroyl vitisin A)

3D SDF for NP0336477 (p-Coumaroyl vitisin A)

3D-SDF for NP0336477 (p-Coumaroyl vitisin A)

PDB for NP0336477 (p-Coumaroyl vitisin A)

3D PDB for NP0336477 (p-Coumaroyl vitisin A)

SMILES for NP0336477 (p-Coumaroyl vitisin A)

INCHI for NP0336477 (p-Coumaroyl vitisin A)

Structure for NP0336477 (p-Coumaroyl vitisin A)

3D Structure for NP0336477 (p-Coumaroyl vitisin A)