NP-MRD: Showing NP-Card for (6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate (NP0060942)

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Record Information

Version

2.0

Created at

2022-04-28 05:53:50 UTC

Updated at

2022-04-28 05:53:51 UTC

NP-MRD ID

NP0060942

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate

Description

[4-(4,5-Dihydroxy-3-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H-chromen-2-ylidene)cyclohexa-2,5-dien-1-ylidene][(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-{[(4-oxo-4-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-5H-chromen-7-yl)oxy]oxan-2-yl]methoxy}butanoyl)oxy]methyl}oxan-2-yl]oxidanium belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified 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. (6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate is found in Agapanthus praecox. Based on a literature review very few articles have been published on [4-(4,5-dihydroxy-3-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H-chromen-2-ylidene)cyclohexa-2,5-dien-1-ylidene][(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-{[(4-oxo-4-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-5H-chromen-7-yl)oxy]oxan-2-yl]methoxy}butanoyl)oxy]methyl}oxan-2-yl]oxidanium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207532D          

113124  0  0  1  0            999 V2000
  -10.7171    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    8.2500    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
  -13.5749    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -14.2894   10.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.5749   11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.5749   11.9625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.2894   12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
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  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
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 27 28  1  0  0  0  0
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 24 29  1  0  0  0  0
 27 30  1  0  0  0  0
 15 31  1  1  0  0  0
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 13 33  1  1  0  0  0
  8 34  1  0  0  0  0
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 48111  1  6  0  0  0
 47112  1  1  0  0  0
 46113  1  6  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

190201  0  0  0  0  0  0  0  0999 V2000
   17.2867    1.9847    1.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5301    0.7671    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8625    0.3152    0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.8152   -0.0968   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  1  97   1
M  END


  Mrv1652304282207532D          

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M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0060942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@@H](OC2=C(OC3=CC(O[C@H]4OC[C@@H](O)[C@@H](O)[C@H]4O)=CC(O)=C3C2=O)C2=CC=C(O[C@@H]3O[C@@H](COC(=O)CCC(=O)OC[C@@H]4O[C@@H](OC5=CC(O)=C6C=C(O[C@@H]7O[C@H](COC(=O)\C=C\C8=CC=C(O)C=C8)[C@@H](O)[C@H](O)[C@H]7O)C(=[O+]C6=C5)C5=CC(O)=C(O)C(O)=C5)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C72H76O41/c73-20-41-51(85)56(90)64(98)72(109-41)113-67-55(89)48-34(76)16-31(104-68-60(94)50(84)37(79)21-102-68)18-39(48)107-66(67)26-4-8-29(9-5-26)103-69-61(95)57(91)52(86)42(110-69)22-100-46(81)11-12-47(82)101-23-43-53(87)58(92)62(96)70(111-43)105-30-15-33(75)32-19-40(65(106-38(32)17-30)27-13-35(77)49(83)36(78)14-27)108-71-63(97)59(93)54(88)44(112-71)24-99-45(80)10-3-25-1-6-28(74)7-2-25/h1-10,13-19,37,41-44,50-54,56-64,68-73,79,84-88,90-98H,11-12,20-24H2,(H5-,74,75,76,77,78,80,83,89)/p+1/t37-,41+,42+,43+,44-,50-,51-,52-,53-,54-,56+,57+,58+,59+,60-,61-,62-,63-,64+,68-,69-,70-,71-,72+/m1/s1

> <INCHI_KEY>
ZGPLUMMVKACNSF-LEPQPZDOSA-O

> <FORMULA>
C72H77O41

> <MOLECULAR_WEIGHT>
1598.366

> <EXACT_MASS>
1597.39347832

> <JCHEM_ACCEPTOR_COUNT>
38

> <JCHEM_ATOM_COUNT>
190

> <JCHEM_AVERAGE_POLARIZABILITY>
149.39359836737077

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
22

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-{[(4-oxo-4-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(5-hydroxy-4-oxo-3-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-2-yl)phenoxy]oxan-2-yl]methoxy}butanoyl)oxy]methyl}oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
-3.716099999999993

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.067301402528684

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.392867022463089

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9542529852651365

> <JCHEM_POLAR_SURFACE_AREA>
655.7000000000003

> <JCHEM_REFRACTIVITY>
374.10489999999976

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-{[(4-oxo-4-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(5-hydroxy-4-oxo-3-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}chromen-2-yl)phenoxy]oxan-2-yl]methoxy}butanoyl)oxy]methyl}oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-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     -20.005  16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -20.005  17.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -21.339  18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -22.673  17.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -22.673  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -21.339  15.400   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -24.006  15.400   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0     -25.340  16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -25.340  17.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -24.006  18.480   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -26.674  18.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -26.674  20.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -25.340  20.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -25.340  22.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -26.674  23.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -28.007  22.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -28.007  20.790   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -29.341  23.100   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -29.341  24.640   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -30.675  25.410   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -32.008  24.640   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -30.675  26.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -29.341  27.720   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -29.341  29.260   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -30.675  30.030   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -30.675  31.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -29.341  32.340   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -28.007  31.570   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -28.007  30.030   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -29.341  33.880   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -26.674  24.640   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -24.006  23.100   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -24.006  20.020   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -26.674  15.400   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -26.674  13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -28.007  13.090   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -29.341  13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -29.341  15.400   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -28.007  16.170   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -30.675  16.170   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -30.675  13.090   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -28.007  11.550   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -21.339  20.020   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -18.672  15.400   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -17.338  16.170   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -17.338  17.710   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -16.004  18.480   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -14.670  17.710   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -14.670  16.170   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -16.004  15.400   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -13.337  15.400   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -13.337  13.860   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -12.003  13.090   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -10.669  13.860   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0     -12.003  11.550   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -12.003   8.470   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   87  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   92  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   97  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM  102  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM  103  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM  104  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM  106  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM  107  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM  108  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM  109  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0     -13.337  18.480   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0     -16.004  20.020   0.000  0.00  0.00           O+0
HETATM  113  O   UNK     0     -18.672  18.480   0.000  0.00  0.00           O+0
CONECT    1    2    6   44                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   31                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31   15                                                            
CONECT   32   14                                                            
CONECT   33   13                                                            
CONECT   34    8   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   34                                                       
CONECT   40   38                                                            
CONECT   41   37                                                            
CONECT   42   36                                                            
CONECT   43    3                                                            
CONECT   44    1   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47  113                                                  
CONECT   47   46   48  112                                                  
CONECT   48   47   49  111                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49   45                                                       
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   66                                                  
CONECT   62   61   63  110                                                  
CONECT   63   62   64  109                                                  
CONECT   64   63   65  108                                                  
CONECT   65   64   66   67                                                  
CONECT   66   65   61                                                       
CONECT   67   65   68                                                       
CONECT   68   67   69   73                                                  
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72   74                                                  
CONECT   72   71   73                                                       
CONECT   73   72   68                                                       
CONECT   74   71   75   80                                                  
CONECT   75   74   76   96                                                  
CONECT   76   75   77   78                                                  
CONECT   77   76                                                            
CONECT   78   76   79   84                                                  
CONECT   79   78   80   81                                                  
CONECT   80   79   74                                                       
CONECT   81   79   82                                                       
CONECT   82   81   83   86                                                  
CONECT   83   82   84                                                       
CONECT   84   83   78   85                                                  
CONECT   85   84                                                            
CONECT   86   82   87                                                       
CONECT   87   86   88   92                                                  
CONECT   88   87   89   95                                                  
CONECT   89   88   90   94                                                  
CONECT   90   89   91   93                                                  
CONECT   91   90   92                                                       
CONECT   92   91   87                                                       
CONECT   93   90                                                            
CONECT   94   89                                                            
CONECT   95   88                                                            
CONECT   96   75   97                                                       
CONECT   97   96   98  102                                                  
CONECT   98   97   99  107                                                  
CONECT   99   98  100  106                                                  
CONECT  100   99  101  105                                                  
CONECT  101  100  102  103                                                  
CONECT  102  101   97                                                       
CONECT  103  101  104                                                       
CONECT  104  103                                                            
CONECT  105  100                                                            
CONECT  106   99                                                            
CONECT  107   98                                                            
CONECT  108   64                                                            
CONECT  109   63                                                            
CONECT  110   62                                                            
CONECT  111   48                                                            
CONECT  112   47                                                            
CONECT  113   46                                                            
MASTER        0    0    0    0    0    0    0    0  113    0  248    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇₂H₇₇O₄₁

Average Mass

1598.3660 Da

Monoisotopic Mass

1597.39348 Da

IUPAC Name

5-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-{[(4-oxo-4-{[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(5-hydroxy-4-oxo-3-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-{[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-4H-chromen-2-yl)phenoxy]oxan-2-yl]methoxy}butanoyl)oxy]methyl}oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@@H](OC2=C(OC3=CC(O[C@H]4OC[C@@H](O)[C@@H](O)[C@H]4O)=CC(O)=C3C2=O)C2=CC=C(O[C@@H]3O[C@@H](COC(=O)CCC(=O)OC[C@@H]4O[C@@H](OC5=CC(O)=C6C=C(O[C@@H]7O[C@H](COC(=O)\C=C\C8=CC=C(O)C=C8)[C@@H](O)[C@H](O)[C@H]7O)C(=[O+]C6=C5)C5=CC(O)=C(O)C(O)=C5)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C72H76O41/c73-20-41-51(85)56(90)64(98)72(109-41)113-67-55(89)48-34(76)16-31(104-68-60(94)50(84)37(79)21-102-68)18-39(48)107-66(67)26-4-8-29(9-5-26)103-69-61(95)57(91)52(86)42(110-69)22-100-46(81)11-12-47(82)101-23-43-53(87)58(92)62(96)70(111-43)105-30-15-33(75)32-19-40(65(106-38(32)17-30)27-13-35(77)49(83)36(78)14-27)108-71-63(97)59(93)54(88)44(112-71)24-99-45(80)10-3-25-1-6-28(74)7-2-25/h1-10,13-19,37,41-44,50-54,56-64,68-73,79,84-88,90-98H,11-12,20-24H2,(H5-,74,75,76,77,78,80,83,89)/p+1/t37-,41+,42+,43+,44-,50-,51-,52-,53-,54-,56+,57+,58+,59+,60-,61-,62-,63-,64+,68-,69-,70-,71-,72+/m1/s1

InChI Key

ZGPLUMMVKACNSF-LEPQPZDOSA-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
Agapanthus praecox	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified 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

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Anthocyanin
Anthocyanidin-7-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-7-o-glycoside
Flavonoid-3-o-glycoside
Saccharolipid
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzenetriol
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
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	2.06	ALOGPS
logP	-3.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	38	ChemAxon
Hydrogen Donor Count	22	ChemAxon
Polar Surface Area	655.7 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	374.1 m³·mol⁻¹	ChemAxon
Polarizability	149.39 Å³	ChemAxon
Number of Rings	12	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

163183865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate (NP0060942)

MOL for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

3D MOL for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

3D SDF for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

3D-SDF for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

PDB for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

3D PDB for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

SMILES for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

INCHI for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

Structure for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)

3D Structure for NP0060942 ((6'''-O-(Delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate)