NP-MRD: Showing NP-Card for 6'-O-trans-p-coumaroylgeniposidic acid (NP0034673)

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Record Information

Version

2.0

Created at

2021-06-20 18:20:08 UTC

Updated at

2021-06-30 00:05:13 UTC

NP-MRD ID

NP0034673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6'-O-trans-p-coumaroylgeniposidic acid

Provided By

JEOL Database JEOL Logo

Description

P-Coumaroylgeniposidic acid 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-coumaroylgeniposidic acid is found in Gardenia jasminoides. 6'-O-trans-p-coumaroylgeniposidic acid was first documented in 2009 (PMID: 19650637). Based on a literature review very few articles have been published on p-Coumaroylgeniposidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120203D          

 65 68  0  0  0  0            999 V2000
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    1.7548   -0.6476   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202120203D          

 65 68  0  0  0  0            999 V2000
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    2.2961   -1.4451    2.6683 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1283   -1.3863    4.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -2.0646    2.3577 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7120   -3.4151    2.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9162    0.6384    2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2324    1.9414    0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    4.5705    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    7.5517    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0862   -0.4604    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1037    0.0834   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3568    1.6693    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4961   -2.0940    2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196   -0.8555    4.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -1.5279    2.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612   -3.3714    3.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2294   -2.7651    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -3.3718    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 37  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 31  1  0  0  0  0
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 22 23  2  0  0  0  0
 13 12  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 32  1  0  0  0  0
 25 52  1  1  0  0  0
 32 34  1  0  0  0  0
 31 59  1  1  0  0  0
 18 17  1  0  0  0  0
 34 36  1  0  0  0  0
 25 21  1  0  0  0  0
  7  8  2  0  0  0  0
 31 18  1  0  0  0  0
  8 10  1  0  0  0  0
 18 19  1  0  0  0  0
 10 11  2  0  0  0  0
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 11  5  1  0  0  0  0
 20 21  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 31 25  1  0  0  0  0
  8  9  1  0  0  0  0
 36 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2  1  2  0  0  0  0
  2 12  1  0  0  0  0
 15 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 14 13  1  0  0  0  0
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 26 53  1  0  0  0  0
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  3 38  1  0  0  0  0
  4 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])OC(=O)C(\[H])=C(/[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@]2([H])C(=C([H])C([H])([H])[C@]12[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O12/c26-9-13-4-7-15-16(23(32)33)10-35-24(19(13)15)37-25-22(31)21(30)20(29)17(36-25)11-34-18(28)8-3-12-1-5-14(27)6-2-12/h1-6,8,10,15,17,19-22,24-27,29-31H,7,9,11H2,(H,32,33)/b8-3+/t15-,17-,19-,20-,21+,22-,24+,25+/m1/s1

> <INCHI_KEY>
XGAAYMVJQOBEJH-KMSLGSAPSA-N

> <FORMULA>
C25H28O12

> <MOLECULAR_WEIGHT>
520.487

> <EXACT_MASS>
520.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.17178343607353

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.13636670166666784

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.397974187491275

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.222500426807435

> <JCHEM_PKA_STRONGEST_BASIC>
-2.735421632953014

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
125.28610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.88e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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    0.6627   -1.5316   -2.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2961   -1.4451    2.6683 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.0047   -5.0713   -4.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -6.5918   -5.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -6.0333   -4.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2294   -2.7651    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -3.3718    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 37  1  0
 25 26  1  0
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 28 31  1  0
 34 35  1  0
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 22 24  1  0
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 29 30  1  0
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 31 59  1  1
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 34 36  1  0
 25 21  1  0
  7  8  2  0
 31 18  1  0
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 11  5  1  0
 20 21  2  0
  5  6  2  0
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 31 25  1  0
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 36 14  1  0
 14 15  1  0
  2  1  2  0
  2 12  1  0
 15 16  1  0
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 14 13  1  0
 16 17  1  0
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 29 56  1  0
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 30 58  1  0
  7 41  1  0
 10 43  1  0
 11 44  1  0
  6 40  1  0
  9 42  1  0
  3 38  1  0
  4 39  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  O   UNK     0       1.639   0.569  -2.253  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.755  -0.648  -2.264  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.663  -1.532  -2.723  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.768  -2.864  -2.847  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.328  -3.731  -3.300  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.023  -4.859  -4.074  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.034  -5.724  -4.500  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.352  -5.471  -4.143  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.307  -6.340  -4.579  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.677  -4.368  -3.362  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.663  -3.503  -2.937  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.836  -1.361  -1.861  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.892  -0.606  -1.236  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.742  -0.644   0.294  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.446  -0.132   0.631  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.205  -0.049   2.028  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.873   0.417   2.258  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.707   1.775   1.825  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.287   2.640   2.813  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.927   3.957   2.719  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.137   4.431   2.056  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.448   5.874   2.030  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.444   6.367   1.533  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.490   6.640   2.611  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.117   3.511   1.393  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.199   3.665  -0.135  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.561   2.286  -0.581  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.351   1.372   0.379  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.546  -0.108   0.316  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.306  -0.473  -0.829  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.803   2.019   1.636  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.296  -1.445   2.668  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.128  -1.386   4.094  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.655  -2.065   2.358  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.712  -3.415   2.845  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.919  -2.065   0.850  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.248  -2.541   0.616  0.00  0.00           O+0
HETATM   38  H   UNK     0      -0.254  -1.001  -2.959  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.705  -3.371  -2.628  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.005  -5.071  -4.361  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.792  -6.592  -5.106  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.171  -6.033  -4.259  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.702  -4.165  -3.069  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.931  -2.655  -2.310  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.893   0.431  -1.592  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.843  -1.050  -1.548  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.509   0.019   0.715  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.916   0.638   2.505  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.232   1.941   0.875  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.613   4.571   3.293  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.147   7.552   2.506  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.115   3.710   1.812  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.250   3.973  -0.587  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.974   4.385  -0.415  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.893   2.065  -1.588  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.586  -0.627   0.265  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.086  -0.460   1.200  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.104   0.083  -0.815  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.357   1.669   2.517  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.496  -2.094   2.290  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.320  -0.856   4.239  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.453  -1.528   2.885  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.361  -3.371   3.758  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.229  -2.765   0.362  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.314  -3.372   1.130  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   12    3                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5   39                                                  
CONECT    5   11    6    4                                                  
CONECT    6    5    7   40                                                  
CONECT    7    8    6   41                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   42                                                       
CONECT   10    8   11   43                                                  
CONECT   11   10    5   44                                                  
CONECT   12   13    2                                                       
CONECT   13   12   14   45   46                                             
CONECT   14   36   15   13   47                                             
CONECT   15   14   16                                                       
CONECT   16   32   15   17   48                                             
CONECT   17   18   16                                                       
CONECT   18   17   31   19   49                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   50                                                  
CONECT   21   22   25   20                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   51                                                       
CONECT   25   26   52   21   31                                             
CONECT   26   25   27   53   54                                             
CONECT   27   26   28   55                                                  
CONECT   28   27   31   29                                                  
CONECT   29   28   30   56   57                                             
CONECT   30   29   58                                                       
CONECT   31   28   59   18   25                                             
CONECT   32   33   16   34   60                                             
CONECT   33   32   61                                                       
CONECT   34   35   32   36   62                                             
CONECT   35   34   63                                                       
CONECT   36   37   34   14   64                                             
CONECT   37   36   65                                                       
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
CONECT   58   30                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   34                                                            
CONECT   63   35                                                            
CONECT   64   36                                                            
CONECT   65   37                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    1.6392    0.5692   -2.2530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548   -0.6476   -2.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -1.5316   -2.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7682   -2.8641   -2.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -3.7313   -3.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1993    3.6647   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5612    2.2859   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511    1.3720    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462   -0.1075    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2961   -1.4451    2.6683 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1283   -1.3863    4.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -2.0646    2.3577 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7120   -3.4151    2.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191   -2.0649    0.8497 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2476   -2.5408    0.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7052   -3.3710   -2.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047   -5.0713   -4.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -6.5918   -5.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -6.0333   -4.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7016   -4.1647   -3.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309   -2.6548   -2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    0.4308   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -1.0505   -1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091    0.0185    0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9162    0.6384    2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2324    1.9414    0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    4.5705    3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    7.5517    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154    3.7100    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    3.9729   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8929    2.0648   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857   -0.6270    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4961   -2.0940    2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4531   -1.5279    2.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612   -3.3714    3.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2294   -2.7651    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -3.3718    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 37  1  0
 25 26  1  0
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 34 35  1  0
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  5  6  2  0
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  8  9  1  0
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  2 12  1  0
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 24 51  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
  7 41  1  0
 10 43  1  0
 11 44  1  0
  6 40  1  0
  9 42  1  0
  3 38  1  0
  4 39  1  0
M  END

View in JSmol

Synonyms

Value	Source
p-Coumaroylgeniposidate	Generator

Chemical Formula

C₂₅H₂₈O₁₂

Average Mass

520.4870 Da

Monoisotopic Mass

520.15808 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])OC(=O)C(\[H])=C(/[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@]2([H])C(=C([H])C([H])([H])[C@]12[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C25H28O12/c26-9-13-4-7-15-16(23(32)33)10-35-24(19(13)15)37-25-22(31)21(30)20(29)17(36-25)11-34-18(28)8-3-12-1-5-14(27)6-2-12/h1-6,8,10,15,17,19-22,24-27,29-31H,7,9,11H2,(H,32,33)/b8-3+/t15-,17-,19-,20-,21+,22-,24+,25+/m1/s1

InChI Key

XGAAYMVJQOBEJH-KMSLGSAPSA-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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Primary alcohol
Carbonyl group
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	0.35	ALOGPS
logP	0.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.29 m³·mol⁻¹	ChemAxon
Polarizability	51.17 Å³	ChemAxon
Number of Rings	4	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

44255335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu Y, Xie ZL, Gao H, Ma WW, Dai Y, Wang Y, Zhong Y, Yao XS: Bioactive iridoid glucosides from the fruit of Gardenia jasminoides. J Nat Prod. 2009 Aug;72(8):1459-64. doi: 10.1021/np900176q. [PubMed:19650637 ]
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-coumaroylgeniposidic acid (NP0034673)

MOL for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

3D MOL for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

3D SDF for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

3D-SDF for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

PDB for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

3D PDB for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

SMILES for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

INCHI for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

Structure for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)

3D Structure for NP0034673 (6'-O-trans-p-coumaroylgeniposidic acid)