NP-MRD: Showing NP-Card for 5-O-caffeoyl-4-O-syringoylquinic acid (NP0035095)

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Record Information

Version

2.0

Created at

2021-06-20 18:38:14 UTC

Updated at

2021-06-30 00:05:53 UTC

NP-MRD ID

NP0035095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-O-caffeoyl-4-O-syringoylquinic acid

Provided By

JEOL Database JEOL Logo

Description

CHEMBL1087666 belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. 5-O-caffeoyl-4-O-syringoylquinic acid is found in Erycibe hainanesis. 5-O-caffeoyl-4-O-syringoylquinic acid was first documented in 2010 (Song, S., et al.). Based on a literature review very few articles have been published on CHEMBL1087666.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120383D          

 64 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120383D          

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    1.5342   -0.2776   -4.5135 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2193    0.0308   -3.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3068   -0.5170   -2.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1751    1.2157   -0.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2283   -0.1475    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840   -0.8401    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.4414    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3898   -2.0703    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962   -2.0871    2.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2447   -2.6834    3.7191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176   -1.4808    3.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358   -1.4959    4.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2164   -0.8541    2.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.2015    1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6286    2.0165    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    3.5181    3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    3.2130    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    1.1276    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0321   -1.7212   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975   -0.6985   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    1.3963   -2.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972   -1.6491   -5.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.1888   -5.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    1.7671   -4.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    1.4949   -7.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1716    1.1183   -2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0806   -1.4895   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8302    0.7530    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -1.4155   -0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2273   -2.5276    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9305   -3.0539    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9347   -1.9798    5.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -0.3892    3.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -2.0664    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689   -2.2673    2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787   -2.8367    4.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -3.3127    3.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1515    5.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0  0  0  0
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  5  6  1  0  0  0  0
 25 32  1  0  0  0  0
  6  7  2  0  0  0  0
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  6  8  1  0  0  0  0
 32 30  2  0  0  0  0
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 37  3  2  0  0  0  0
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  4  5  2  0  0  0  0
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 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
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  2  1  1  0  0  0  0
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 36 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1(O[H])C([H])([H])[C@]([H])(O[H])[C@]([H])(OC(=O)C2=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C2[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O13/c1-35-17-8-13(9-18(36-2)21(17)30)23(31)38-22-16(28)10-25(34,24(32)33)11-19(22)37-20(29)6-4-12-3-5-14(26)15(27)7-12/h3-9,16,19,22,26-28,30,34H,10-11H2,1-2H3,(H,32,33)/b6-4+/t16-,19-,22-,25+/m0/s1

> <INCHI_KEY>
YAVQVQGHJZVPCC-XGXRDLAHSA-N

> <FORMULA>
C25H26O13

> <MOLECULAR_WEIGHT>
534.47

> <EXACT_MASS>
534.137340897

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.355953908273605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4S,5S)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(4-hydroxy-3,5-dimethoxybenzoyloxy)cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.6078622376666662

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.363191799268254

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.960305137256861

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2468923999257937

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
127.96399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4S,5S)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(4-hydroxy-3,5-dimethoxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    0.8426    2.7355    2.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    2.1232    3.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    1.0460    2.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638    0.6062    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702   -0.5141    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -1.0179   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -2.0258   -0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.2005   -1.2667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1055   -0.6314   -2.6129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2583   -0.2219   -3.5468 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4706    1.1978   -3.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5596   -5.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.0850   -5.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2525    1.5229   -5.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.3776   -6.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -1.5407   -7.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578    0.6771   -7.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -0.2776   -4.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    0.0308   -3.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3068   -0.5170   -2.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    0.1696   -1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751    1.2157   -0.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -0.5831   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283   -0.1475    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840   -0.8401    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.4414    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3898   -2.0703    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962   -2.0871    2.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2447   -2.6834    3.7191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176   -1.4808    3.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358   -1.4959    4.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2164   -0.8541    2.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.2015    1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -0.7683    3.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2599   -1.3413    3.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.4996    3.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    0.3539    3.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045    0.7745    4.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    2.0165    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    3.5181    3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    3.2130    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    1.1276    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0321   -1.7212   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975   -0.6985   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    1.3963   -2.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972   -1.6491   -5.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.1888   -5.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    1.7671   -4.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    1.4949   -7.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7892   -1.3415   -4.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.2696   -4.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    1.1183   -2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0806   -1.4895   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8302    0.7530    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -1.4155   -0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2273   -2.5276    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9305   -3.0539    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9347   -1.9798    5.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -0.3892    3.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -2.0664    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689   -2.2673    2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787   -2.8367    4.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -3.3127    3.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1515    5.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 37  1  0
 26 25  2  0
 37 38  1  0
 21 20  1  0
 34 35  1  0
 28 27  2  0
  3  2  1  0
 21 22  2  0
  5  6  1  0
 25 32  1  0
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 28 29  1  0
  6  8  1  0
 32 30  2  0
 30 31  1  0
 30 28  1  0
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 37  3  2  0
 27 26  1  0
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 10 12  1  0
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 13 18  1  0
 18 19  1  0
 19  9  1  0
  9 10  1  0
 13 15  1  0
 15 16  2  0
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 15 17  1  0
 23 21  1  0
  2  1  1  0
 33 34  2  0
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 19 20  1  0
 13 14  1  6
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 29 57  1  0
 31 58  1  0
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 10 44  1  1
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 17 49  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 36 61  1  0
 36 62  1  0
 36 63  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.843   2.736   2.417  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.189   2.123   3.180  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.829   1.046   2.628  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.664   0.606   1.314  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.370  -0.514   0.846  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.215  -1.018  -0.546  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.757  -2.026  -0.969  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.411  -0.201  -1.267  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.106  -0.631  -2.613  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.258  -0.222  -3.547  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.471   1.198  -3.471  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.941  -0.560  -5.001  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.380   0.085  -5.447  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.253   1.523  -5.491  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.708  -0.378  -6.874  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.832  -1.541  -7.225  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.858   0.677  -7.716  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.534  -0.278  -4.513  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.219   0.031  -3.046  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.307  -0.517  -2.263  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.658   0.170  -1.147  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.175   1.216  -0.748  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.736  -0.583  -0.477  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.228  -0.148   0.693  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.284  -0.840   1.443  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.384  -1.441   0.807  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.390  -2.070   1.551  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.296  -2.087   2.936  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.245  -2.683   3.719  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.218  -1.481   3.573  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.136  -1.496   4.936  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.216  -0.854   2.842  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.251  -1.202   1.696  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.431  -0.768   3.007  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.260  -1.341   3.939  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.981  -2.500   3.532  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.720   0.354   3.458  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.905   0.775   4.753  0.00  0.00           O+0
HETATM   39  H   UNK     0       1.629   2.017   2.163  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.295   3.518   3.034  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.436   3.213   1.519  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.012   1.128   0.645  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.032  -1.721  -2.621  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.197  -0.699  -3.248  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.674   1.396  -2.534  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.897  -1.649  -5.121  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.754  -0.189  -5.639  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.480   1.767  -4.877  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.710   1.495  -7.179  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.789  -1.341  -4.614  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.443   0.270  -4.798  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.172   1.118  -2.907  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.081  -1.490  -0.958  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.830   0.753   1.158  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.479  -1.416  -0.276  0.00  0.00           H+0
HETATM   56  H   UNK     0       8.227  -2.528   1.034  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.931  -3.054   3.137  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.935  -1.980   5.226  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.388  -0.389   3.371  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.781  -2.066   1.309  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.669  -2.267   2.712  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.579  -2.837   4.384  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.300  -3.313   3.260  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.547   0.152   5.141  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    3    1                                                       
CONECT    3    2   37    4                                                  
CONECT    4    3    5   42                                                  
CONECT    5    6    4   33                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9   19   10    8   43                                             
CONECT   10   12    9   11   44                                             
CONECT   11   10   45                                                       
CONECT   12   10   13   46   47                                             
CONECT   13   12   18   15   14                                             
CONECT   14   13   48                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   49                                                       
CONECT   18   13   19   50   51                                             
CONECT   19   18    9   20   52                                             
CONECT   20   21   19                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   24   21   53                                                  
CONECT   24   25   23   54                                                  
CONECT   25   26   32   24                                                  
CONECT   26   25   27   55                                                  
CONECT   27   28   26   56                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   57                                                       
CONECT   30   32   31   28                                                  
CONECT   31   30   58                                                       
CONECT   32   25   30   59                                                  
CONECT   33    5   34   60                                                  
CONECT   34   37   35   33                                                  
CONECT   35   34   36                                                       
CONECT   36   35   61   62   63                                             
CONECT   37   34   38    3                                                  
CONECT   38   37   64                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    4                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   14                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
CONECT   58   31                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
CONECT   61   36                                                            
CONECT   62   36                                                            
CONECT   63   36                                                            
CONECT   64   38                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
    0.8426    2.7355    2.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    2.1232    3.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290    1.0460    2.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638    0.6062    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702   -0.5141    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -1.0179   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -2.0258   -0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.2005   -1.2667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1055   -0.6314   -2.6129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2583   -0.2219   -3.5468 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4706    1.1978   -3.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9410   -0.5596   -5.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.0850   -5.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2525    1.5229   -5.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.3776   -6.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -1.5407   -7.2249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578    0.6771   -7.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -0.2776   -4.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193    0.0308   -3.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3068   -0.5170   -2.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    0.1696   -1.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751    1.2157   -0.7480 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -0.5831   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283   -0.1475    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840   -0.8401    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.4414    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3898   -2.0703    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962   -2.0871    2.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2447   -2.6834    3.7191 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176   -1.4808    3.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358   -1.4959    4.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2164   -0.8541    2.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.2015    1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -0.7683    3.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2599   -1.3413    3.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.4996    3.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    0.3539    3.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045    0.7745    4.7533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    2.0165    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    3.5181    3.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    3.2130    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117    1.1276    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0321   -1.7212   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975   -0.6985   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    1.3963   -2.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972   -1.6491   -5.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.1888   -5.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4800    1.7671   -4.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    1.4949   -7.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7892   -1.3415   -4.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.2696   -4.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    1.1183   -2.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0806   -1.4895   -0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8302    0.7530    1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -1.4155   -0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2273   -2.5276    1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9305   -3.0539    3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9347   -1.9798    5.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884   -0.3892    3.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -2.0664    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689   -2.2673    2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5787   -2.8367    4.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -3.3127    3.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473    0.1515    5.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 37  1  0
 26 25  2  0
 37 38  1  0
 21 20  1  0
 34 35  1  0
 28 27  2  0
  3  2  1  0
 21 22  2  0
  5  6  1  0
 25 32  1  0
  6  7  2  0
 28 29  1  0
  6  8  1  0
 32 30  2  0
 30 31  1  0
 30 28  1  0
 25 24  1  0
 37  3  2  0
 27 26  1  0
  3  4  1  0
 24 23  2  0
  4  5  2  0
 10 12  1  0
 12 13  1  0
 13 18  1  0
 18 19  1  0
 19  9  1  0
  9 10  1  0
 13 15  1  0
 15 16  2  0
  5 33  1  0
 15 17  1  0
 23 21  1  0
  2  1  1  0
 33 34  2  0
 35 36  1  0
 10 11  1  0
  9  8  1  0
 19 20  1  0
 13 14  1  6
 27 56  1  0
 26 55  1  0
 32 59  1  0
 24 54  1  0
 23 53  1  0
 29 57  1  0
 31 58  1  0
  4 42  1  0
 33 60  1  0
 38 64  1  0
 11 45  1  0
 14 48  1  0
 10 44  1  1
 18 50  1  0
 18 51  1  0
  9 43  1  1
 12 46  1  0
 12 47  1  0
 19 52  1  6
 17 49  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 36 61  1  0
 36 62  1  0
 36 63  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₁₃

Average Mass

534.4700 Da

Monoisotopic Mass

534.13734 Da

IUPAC Name

(1R,3S,4S,5S)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(4-hydroxy-3,5-dimethoxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

(1R,3S,4S,5S)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(4-hydroxy-3,5-dimethoxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1(O[H])C([H])([H])[C@]([H])(O[H])[C@]([H])(OC(=O)C2=C([H])C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C2[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])C1([H])[H]

InChI Identifier

InChI=1S/C25H26O13/c1-35-17-8-13(9-18(36-2)21(17)30)23(31)38-22-16(28)10-25(34,24(32)33)11-19(22)37-20(29)6-4-12-3-5-14(26)15(27)7-12/h3-9,16,19,22,26-28,30,34H,10-11H2,1-2H3,(H,32,33)/b6-4+/t16-,19-,22-,25+/m0/s1

InChI Key

YAVQVQGHJZVPCC-XGXRDLAHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erycibe hainanesis	JEOL database	Song, S., et al, J. Nat. Prod. 73, 177 (2010)

Chemical Taxonomy

Classification

Not classified

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	2.21	ALOGPS
logP	1.61	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	127.96 m³·mol⁻¹	ChemAxon
Polarizability	52.36 Å³	ChemAxon
Number of Rings	3	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

24664825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46185340

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Song, S., et al. (2010). Song, S., et al, J. Nat. Prod. 73, 177 (2010). J. Nat. Prod..

Showing NP-Card for 5-O-caffeoyl-4-O-syringoylquinic acid (NP0035095)

MOL for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

3D MOL for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

3D SDF for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

3D-SDF for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

PDB for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

3D PDB for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

SMILES for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

INCHI for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

Structure for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)

3D Structure for NP0035095 (5-O-caffeoyl-4-O-syringoylquinic acid)