NP-MRD: Showing NP-Card for Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside (NP0057874)

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Record Information

Version

1.0

Created at

2022-04-28 03:14:22 UTC

Updated at

2022-04-28 03:14:22 UTC

NP-MRD ID

NP0057874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside

Description

3-{[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-({[(2E)-3-(3-hydroxy-4-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6S)-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-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside is found in Ipomoea asarifolia . It was first documented in 2022 (PMID: 35501128). Based on a literature review a significant number of articles have been published on 3-{[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-({[(2E)-3-(3-hydroxy-4-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium (PMID: 35501127) (PMID: 35501126) (PMID: 35501125) (PMID: 35501124).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205142D          

 99108  0  0  1  0            999 V2000
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 16 55  1  6  0  0  0
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 58 57  1  6  0  0  0
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M  CHG  1   8   1
M  END

     RDKit          3D

168177  0  0  0  0  0  0  0  0999 V2000
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   -4.4435   11.7112    3.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  1  62   1
M  END


  Mrv1652304282205142D          

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M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0057874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@@H](OC2=C3C=C(O[C@@H]4O[C@@H](COC(=O)\C=C\C5=CC=C(O[C@@H]6O[C@H](COC(=O)\C=C\C7=CC=C(O)C=C7)[C@@H](O)[C@@H](O)[C@H]6O)C(O)=C5)[C@@H](O)[C@H](O)[C@@H]4O[C@@H]4O[C@@H](COC(=O)\C=C\C5=CC=C(O)C=C5)[C@@H](O)[C@@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C66H68O33/c67-24-43-50(77)54(81)58(85)64(95-43)93-41-22-34(70)21-40-35(41)23-42(61(91-40)31-9-14-36(71)37(72)20-31)94-66-62(99-65-60(87)56(83)52(79)45(97-65)26-89-48(75)17-7-29-3-12-33(69)13-4-29)57(84)53(80)46(98-66)27-90-49(76)18-8-30-5-15-39(38(73)19-30)92-63-59(86)55(82)51(78)44(96-63)25-88-47(74)16-6-28-1-10-32(68)11-2-28/h1-23,43-46,50-60,62-67,77-87H,24-27H2,(H5-,68,69,70,71,72,73,74,75)/p+1/b18-8+/t43-,44+,45-,46-,50+,51+,52+,53+,54-,55+,56+,57-,58+,59+,60+,62-,63+,64+,65-,66+/m0/s1

> <INCHI_KEY>
DESIAOCLZCPBTI-OCXMSFNHSA-O

> <FORMULA>
C66H69O33

> <MOLECULAR_WEIGHT>
1390.244

> <EXACT_MASS>
1389.371561102

> <JCHEM_ACCEPTOR_COUNT>
30

> <JCHEM_ATOM_COUNT>
168

> <JCHEM_AVERAGE_POLARIZABILITY>
129.72313597661875

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
18

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.9003999999999985

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.952292107084483

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.646238679133018

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540783867535003

> <JCHEM_POLAR_SURFACE_AREA>
530.0200000000002

> <JCHEM_REFRACTIVITY>
339.5862999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-({[(2E)-3-(3-hydroxy-4-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6S)-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       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667 -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       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667 -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       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.000 -18.480   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000 -23.100   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      21.339  -9.240   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      22.673 -10.010   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       8.709  -8.337   0.000  0.00  0.00           O+0
HETATM   80  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   86  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   89  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   94  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   95  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   96  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2    6   88                                                  
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   80                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    2                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   57                                                  
CONECT   15   14   16   56                                                  
CONECT   16   15   17   55                                                  
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   54                                                  
CONECT   35   34   36   53                                                  
CONECT   36   35   37   52                                                  
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                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49   45                                                       
CONECT   51   48                                                            
CONECT   52   36                                                            
CONECT   53   35                                                            
CONECT   54   34                                                            
CONECT   55   16                                                            
CONECT   56   15                                                            
CONECT   57   14   58                                                       
CONECT   58   57   59   63                                                  
CONECT   59   58   60   79                                                  
CONECT   60   59   61   78                                                  
CONECT   61   60   62   77                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62   58                                                       
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71   75                                                  
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74   76                                                  
CONECT   74   73   75                                                       
CONECT   75   74   70                                                       
CONECT   76   73                                                            
CONECT   77   61                                                            
CONECT   78   60                                                            
CONECT   79   59                                                            
CONECT   80    9   81   85                                                  
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84   87                                                  
CONECT   84   83   85   86                                                  
CONECT   85   84   80                                                       
CONECT   86   84                                                            
CONECT   87   83                                                            
CONECT   88    1   89                                                       
CONECT   89   88   90   94                                                  
CONECT   90   89   91   99                                                  
CONECT   91   90   92   98                                                  
CONECT   92   91   93   97                                                  
CONECT   93   92   94   95                                                  
CONECT   94   93   89                                                       
CONECT   95   93   96                                                       
CONECT   96   95                                                            
CONECT   97   92                                                            
CONECT   98   91                                                            
CONECT   99   90                                                            
MASTER        0    0    0    0    0    0    0    0   99    0  216    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆₆H₆₉O₃₃

Average Mass

1390.2440 Da

Monoisotopic Mass

1389.37156 Da

IUPAC Name

3-{[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-({[(2E)-3-(3-hydroxy-4-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6S)-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=C3C=C(O[C@@H]4O[C@@H](COC(=O)\C=C\C5=CC=C(O[C@@H]6O[C@H](COC(=O)\C=C\C7=CC=C(O)C=C7)[C@@H](O)[C@@H](O)[C@H]6O)C(O)=C5)[C@@H](O)[C@H](O)[C@@H]4O[C@@H]4O[C@@H](COC(=O)\C=C\C5=CC=C(O)C=C5)[C@@H](O)[C@@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C66H68O33/c67-24-43-50(77)54(81)58(85)64(95-43)93-41-22-34(70)21-40-35(41)23-42(61(91-40)31-9-14-36(71)37(72)20-31)94-66-62(99-65-60(87)56(83)52(79)45(97-65)26-89-48(75)17-7-29-3-12-33(69)13-4-29)57(84)53(80)46(98-66)27-90-49(76)18-8-30-5-15-39(38(73)19-30)92-63-59(86)55(82)51(78)44(96-63)25-88-47(74)16-6-28-1-10-32(68)11-2-28/h1-23,43-46,50-60,62-67,77-87H,24-27H2,(H5-,68,69,70,71,72,73,74,75)/p+1/b18-8+/t43-,44+,45-,46-,50+,51+,52+,53+,54-,55+,56+,57-,58+,59+,60+,62-,63+,64+,65-,66+/m0/s1

InChI Key

DESIAOCLZCPBTI-OCXMSFNHSA-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 asarifolia	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
Coumaric acid ester
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	2.92	ALOGPS
logP	2.9	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.65	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	30	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	530.02 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	339.59 m³·mol⁻¹	ChemAxon
Polarizability	129.72 Å³	ChemAxon
Number of Rings	10	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

163191964

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Booke F, Fauser D, Reims N, Bethge M: Unemployment due to the SARS-CoV-2-pandemic among people with and without severe disabilities: a difference-in-differences analysis. Occup Environ Med. 2022 May 2. pii: oemed-2021-108125. doi: 10.1136/oemed-2021-108125. [PubMed:35501128 ]
Ritonja JA, Aronson KJ, Leung M, Flaten L, Topouza DG, Duan QL, Durocher F, Tranmer JE, Bhatti P: Investigating the relationship between melatonin patterns and methylation in circadian genes among day shift and night shift workers. Occup Environ Med. 2022 May 2. pii: oemed-2021-108111. doi: 10.1136/oemed-2021-108111. [PubMed:35501127 ]
Kelly-Reif K, Bertke SJ, Samet J, Sood A, Schubauer-Berigan MK: Health burdens of uranium miners will extend beyond the radiation exposure compensation act deadline. Occup Environ Med. 2022 May 2. pii: oemed-2022-108311. doi: 10.1136/oemed-2022-108311. [PubMed:35501126 ]
Guseva Canu I, Gaillen-Guedy A, Antilla A, Charles S, Fraize-Frontier S, Luce D, McElvenny DM, Merletti F, Michel C, Pukkala E, Schubauer-Berigan MK, Straif K, Wild P, Richardson DB: Lung cancer mortality in the European cohort of titanium dioxide workers: a reanalysis of the exposure-response relationship. Occup Environ Med. 2022 May 2. pii: oemed-2021-108030. doi: 10.1136/oemed-2021-108030. [PubMed:35501125 ]
Ferrari V, Cristofani R, Cicardi ME, Tedesco B, Crippa V, Chierichetti M, Casarotto E, Cozzi M, Mina F, Galbiati M, Piccolella M, Carra S, Vaccari T, Nalbandian A, Kimonis V, Fortuna TR, Pandey UB, Gagliani MC, Cortese K, Rusmini P, Poletti A: Pathogenic variants of Valosin Containing Protein induce lysosomal damage and transcriptional activation of autophagy regulators in neuronal cells. Neuropathol Appl Neurobiol. 2022 May 2:e12818. doi: 10.1111/nan.12818. [PubMed:35501124 ]

Showing NP-Card for Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside (NP0057874)

MOL for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

3D MOL for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

3D SDF for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

3D-SDF for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

PDB for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

3D PDB for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

SMILES for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

INCHI for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

Structure for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)

3D Structure for NP0057874 (Cyanidin 3-O-[2-O-(6-O-E-coumaroyl-beta-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl}-5-O-beta-D-glucopyranoside)