NP-MRD: Showing NP-Card for 6''-O-trans-p-coumaroylgenipin gentiobioside (NP0034671)

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Record Information

Version

2.0

Created at

2021-06-20 18:20:03 UTC

Updated at

2021-06-30 00:05:13 UTC

NP-MRD ID

NP0034671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6''-O-trans-p-coumaroylgenipin gentiobioside

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2296791 belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. 6''-O-trans-p-coumaroylgenipin gentiobioside is found in Gardenia jasminoides. 6''-O-trans-p-coumaroylgenipin gentiobioside was first documented in 2009 (Yu, Y., et al.). Based on a literature review very few articles have been published on CHEMBL2296791.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120203D          

 89 93  0  0  0  0            999 V2000
   -4.7576   -4.5061    3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -4.0559    2.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0659   -3.0069   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
   -4.7576   -4.5061    3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120203D          

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M  END
> <DATABASE_ID>
NP0034671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(OC([H])([H])[C@@]3([H])O[C@@]([H])(O[C@]4([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]5([H])C([H])([H])C([H])=C(C([H])([H])O[H])[C@@]45[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]3([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O17/c1-43-29(42)18-11-45-30(22-15(10-33)5-8-17(18)22)49-32-28(41)26(39)24(37)20(48-32)13-46-31-27(40)25(38)23(36)19(47-31)12-44-21(35)9-4-14-2-6-16(34)7-3-14/h2-7,9,11,17,19-20,22-28,30-34,36-41H,8,10,12-13H2,1H3/b9-4+/t17-,19-,20-,22-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1

> <INCHI_KEY>
QIWWLKDHHMGRQL-QJIBEZHESA-N

> <FORMULA>
C32H40O17

> <MOLECULAR_WEIGHT>
696.655

> <EXACT_MASS>
696.226549828

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.42228367253962

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
-1.2552415546666682

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.91025491789545

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397306298568104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7354216333590458

> <JCHEM_POLAR_SURFACE_AREA>
260.59

> <JCHEM_REFRACTIVITY>
162.46850000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
   -4.7576   -4.5061    3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -4.0559    2.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3162   -3.1975    1.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4750   -2.8130    1.7411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743   -2.7427    0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -3.3334    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659   -3.0069   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -1.7115   -0.7036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3132   -1.7053   -1.8694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.5865   -1.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3378   -0.2138   -1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -0.0138   -0.8574 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8869    1.4566   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9827    1.7463    0.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    3.1450    0.9027 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5908    3.3300    2.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807    2.9196    2.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3742    1.7236    3.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    0.5148    2.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691   -0.3686    3.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -0.2915    4.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -1.4696    2.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7113   -2.3382    2.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470   -3.3810    1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735   -4.2349    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -5.1968    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458   -5.3136   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1272   -6.2264   -0.9848 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7284   -4.4950    0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3801   -3.5301    1.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232    2.7066    1.5703 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0643    2.7265    2.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    3.8429    0.5683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5314    3.7543   -0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8743    3.8362   -0.0335 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2608    5.1931   -0.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513   -0.4044   -2.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0190   -0.2738   -1.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3791   -1.8515   -2.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1660   -2.1492   -3.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.0639   -2.7273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6619   -3.4526   -3.0096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5722   -1.3444   -1.1759 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7458    0.1439   -1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    0.8835   -2.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8854    1.4953   -1.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5607    0.6818   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0223   -0.3229    0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6669   -1.6634   -0.1333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2460   -5.1852    4.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5695   -5.0542    3.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1494   -3.6612    4.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -4.1817    1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -0.9690    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -2.2074   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -0.6264    0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604    2.0991   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    1.6516   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    3.5979    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    3.7537    3.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524    1.9284    4.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    1.5819    4.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -1.4954    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573   -2.2550    3.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -4.1585    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478   -5.8396   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -6.7055   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7621   -4.6015    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1572   -2.8873    1.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    1.7420    1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    3.0037    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7359    4.8010    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281    2.9497   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645    3.3366   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    5.5861   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933    0.2580   -2.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316   -0.7220   -2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229   -2.5452   -1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842   -3.0455   -3.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123   -1.5120   -3.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -3.5508   -3.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030   -1.8772   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    1.6777   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    0.2348   -3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    0.7844   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.7327   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5055   -0.1692    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1011   -0.2410    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5533   -2.0089   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 15 35  1  0
 35 33  1  0
 10 41  1  0
 41 39  1  0
 39 37  1  0
 37 12  1  0
 12 11  1  0
 11 10  1  0
 37 38  1  0
 39 40  1  0
 41 42  1  0
 13 14  1  0
 33 31  1  0
 31 17  1  0
 17 16  1  0
 16 15  1  0
 49  5  1  0
 43  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
 43 49  1  0
 31 32  1  0
 33 34  1  0
 35 36  1  0
 49 48  1  0
 48 47  1  0
 47 44  2  0
 44 43  1  0
 18 19  1  0
  5  3  1  0
 27 29  1  0
  3  2  1  0
 24 25  2  0
  3  4  2  0
 25 26  1  0
  2  1  1  0
 26 27  2  0
 44 45  1  0
 27 28  1  0
 45 46  1  0
 29 30  2  0
 49 89  1  6
 43 82  1  6
  8  9  1  0
 20 21  2  0
 20 22  1  0
 30 24  1  0
 22 23  2  0
 23 24  1  0
 17 18  1  0
 15 14  1  0
 12 13  1  0
 10  9  1  0
 26 66  1  0
 29 68  1  0
 30 69  1  0
 25 65  1  0
 28 67  1  0
 15 59  1  1
 31 70  1  6
 32 71  1  0
 33 72  1  1
 34 73  1  0
 35 74  1  6
 36 75  1  0
 18 61  1  0
 18 62  1  0
 17 60  1  1
 10 55  1  1
 37 76  1  6
 38 77  1  0
 39 78  1  1
 40 79  1  0
 41 80  1  6
 42 81  1  0
 13 57  1  0
 13 58  1  0
 12 56  1  1
  8 54  1  1
  6 53  1  0
 48 87  1  0
 48 88  1  0
 47 86  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
 45 83  1  0
 45 84  1  0
 46 85  1  0
 22 63  1  0
 23 64  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      -4.758  -4.506   3.673  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.806  -4.056   2.707  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.316  -3.197   1.789  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.475  -2.813   1.741  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.274  -2.743   0.830  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.074  -3.333   0.766  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.066  -3.007  -0.096  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.155  -1.712  -0.704  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.313  -1.705  -1.869  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.065  -1.587  -1.524  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.338  -0.214  -1.255  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.712  -0.014  -0.857  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.887   1.457  -0.460  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.983   1.746   0.617  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.899   3.145   0.903  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.591   3.330   2.286  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.281   2.920   2.712  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.374   1.724   3.672  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.651   0.515   2.948  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.469  -0.369   3.565  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.940  -0.292   4.686  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.710  -1.470   2.613  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.711  -2.338   2.816  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.047  -3.381   1.843  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.074  -4.235   1.307  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.420  -5.197   0.354  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.746  -5.314  -0.048  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.127  -6.226  -0.985  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.728  -4.495   0.495  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.380  -3.530   1.442  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.723   2.707   1.570  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.064   2.727   2.076  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.536   3.843   0.568  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.531   3.754  -0.467  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.874   3.836  -0.034  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.261   5.193  -0.315  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.651  -0.404  -2.006  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.019  -0.274  -1.620  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.379  -1.851  -2.432  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.166  -2.149  -3.596  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.895  -2.064  -2.727  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.662  -3.453  -3.010  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.572  -1.344  -1.176  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.746   0.144  -1.384  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.039   0.884  -2.463  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.885   1.495  -1.893  0.00  0.00           O+0
HETATM   47  C   UNK     0      -3.561   0.682  -0.467  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.022  -0.323   0.533  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.667  -1.663  -0.133  0.00  0.00           C+0
HETATM   50  H   UNK     0      -4.246  -5.185   4.361  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.569  -5.054   3.185  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.149  -3.661   4.248  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.778  -4.182   1.373  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.795  -0.969   0.023  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.283  -2.207  -0.648  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.910  -0.626   0.030  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.660   2.099  -1.317  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.911   1.652  -0.123  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.888   3.598   0.764  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.082   3.754   3.328  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.152   1.928   4.416  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.581   1.582   4.189  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.080  -1.495   1.735  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.357  -2.255   3.688  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.037  -4.159   1.625  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.648  -5.840  -0.057  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.340  -6.705  -1.292  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.762  -4.601   0.178  0.00  0.00           H+0
HETATM   69  H   UNK     0       5.157  -2.887   1.851  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.592   1.742   1.068  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.623   3.004   1.323  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.736   4.801   1.064  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.328   2.950  -0.999  0.00  0.00           H+0
HETATM   74  H   UNK     0       0.865   3.337  -1.007  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.531   5.586  -0.830  0.00  0.00           H+0
HETATM   76  H   UNK     0       3.493   0.258  -2.867  0.00  0.00           H+0
HETATM   77  H   UNK     0       5.532  -0.722  -2.324  0.00  0.00           H+0
HETATM   78  H   UNK     0       3.723  -2.545  -1.657  0.00  0.00           H+0
HETATM   79  H   UNK     0       3.884  -3.046  -3.871  0.00  0.00           H+0
HETATM   80  H   UNK     0       1.612  -1.512  -3.632  0.00  0.00           H+0
HETATM   81  H   UNK     0       0.691  -3.551  -3.062  0.00  0.00           H+0
HETATM   82  H   UNK     0      -2.803  -1.877  -2.108  0.00  0.00           H+0
HETATM   83  H   UNK     0      -2.673   1.678  -2.869  0.00  0.00           H+0
HETATM   84  H   UNK     0      -1.744   0.235  -3.293  0.00  0.00           H+0
HETATM   85  H   UNK     0      -0.220   0.784  -1.773  0.00  0.00           H+0
HETATM   86  H   UNK     0      -3.814   1.733  -0.408  0.00  0.00           H+0
HETATM   87  H   UNK     0      -3.506  -0.169   1.487  0.00  0.00           H+0
HETATM   88  H   UNK     0      -5.101  -0.241   0.700  0.00  0.00           H+0
HETATM   89  H   UNK     0      -4.553  -2.009  -0.688  0.00  0.00           H+0
CONECT    1    2   50   51   52                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   49    6    3                                                  
CONECT    6    7    5   53                                                  
CONECT    7    8    6                                                       
CONECT    8   43    7    9   54                                             
CONECT    9    8   10                                                       
CONECT   10   41   11    9   55                                             
CONECT   11   12   10                                                       
CONECT   12   37   11   13   56                                             
CONECT   13   14   12   57   58                                             
CONECT   14   13   15                                                       
CONECT   15   35   16   14   59                                             
CONECT   16   17   15                                                       
CONECT   17   31   16   18   60                                             
CONECT   18   19   17   61   62                                             
CONECT   19   20   18                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   63                                                  
CONECT   23   22   24   64                                                  
CONECT   24   25   30   23                                                  
CONECT   25   24   26   65                                                  
CONECT   26   25   27   66                                                  
CONECT   27   29   26   28                                                  
CONECT   28   27   67                                                       
CONECT   29   27   30   68                                                  
CONECT   30   29   24   69                                                  
CONECT   31   33   17   32   70                                             
CONECT   32   31   71                                                       
CONECT   33   35   31   34   72                                             
CONECT   34   33   73                                                       
CONECT   35   15   33   36   74                                             
CONECT   36   35   75                                                       
CONECT   37   39   12   38   76                                             
CONECT   38   37   77                                                       
CONECT   39   41   37   40   78                                             
CONECT   40   39   79                                                       
CONECT   41   10   39   42   80                                             
CONECT   42   41   81                                                       
CONECT   43    8   49   44   82                                             
CONECT   44   47   43   45                                                  
CONECT   45   44   46   83   84                                             
CONECT   46   45   85                                                       
CONECT   47   48   44   86                                                  
CONECT   48   49   47   87   88                                             
CONECT   49    5   43   48   89                                             
CONECT   50    1                                                            
CONECT   51    1                                                            
CONECT   52    1                                                            
CONECT   53    6                                                            
CONECT   54    8                                                            
CONECT   55   10                                                            
CONECT   56   12                                                            
CONECT   57   13                                                            
CONECT   58   13                                                            
CONECT   59   15                                                            
CONECT   60   17                                                            
CONECT   61   18                                                            
CONECT   62   18                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   28                                                            
CONECT   68   29                                                            
CONECT   69   30                                                            
CONECT   70   31                                                            
CONECT   71   32                                                            
CONECT   72   33                                                            
CONECT   73   34                                                            
CONECT   74   35                                                            
CONECT   75   36                                                            
CONECT   76   37                                                            
CONECT   77   38                                                            
CONECT   78   39                                                            
CONECT   79   40                                                            
CONECT   80   41                                                            
CONECT   81   42                                                            
CONECT   82   43                                                            
CONECT   83   45                                                            
CONECT   84   45                                                            
CONECT   85   46                                                            
CONECT   86   47                                                            
CONECT   87   48                                                            
CONECT   88   48                                                            
CONECT   89   49                                                            
MASTER        0    0    0    0    0    0    0    0   89    0  186    0
END

RDKit          3D

89 93  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₀O₁₇

Average Mass

696.6550 Da

Monoisotopic Mass

696.22655 Da

IUPAC Name

methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(OC([H])([H])[C@@]3([H])O[C@@]([H])(O[C@]4([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]5([H])C([H])([H])C([H])=C(C([H])([H])O[H])[C@@]45[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]3([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C32H40O17/c1-43-29(42)18-11-45-30(22-15(10-33)5-8-17(18)22)49-32-28(41)26(39)24(37)20(48-32)13-46-31-27(40)25(38)23(36)19(47-31)12-44-21(35)9-4-14-2-6-16(34)7-3-14/h2-7,9,11,17,19-20,22-28,30-34,36-41H,8,10,12-13H2,1H3/b9-4+/t17-,19-,20-,22-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1

InChI Key

QIWWLKDHHMGRQL-QJIBEZHESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Gardenia jasminoides	JEOL database	Yu, Y., et al, J. Nat. Prod. 72, 1459 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Iridoid-skeleton
Monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Oxane
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
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	-0.32	ALOGPS
logP	-1.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	260.59 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	162.47 m³·mol⁻¹	ChemAxon
Polarizability	66.42 Å³	ChemAxon
Number of Rings	5	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

10392856

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6324973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu, Y., et al. (2009). Yu, Y., et al, J. Nat. Prod. 72, 1459 (2009). J. Nat. Prod..

Showing NP-Card for 6''-O-trans-p-coumaroylgenipin gentiobioside (NP0034671)

MOL for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

3D MOL for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

3D SDF for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

3D-SDF for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

PDB for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

3D PDB for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

SMILES for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

INCHI for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

Structure for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)

3D Structure for NP0034671 (6''-O-trans-p-coumaroylgenipin gentiobioside)