NP-MRD: Showing NP-Card for 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside (NP0038530)

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Record Information

Version

2.0

Created at

2021-06-20 21:11:54 UTC

Updated at

2021-06-30 00:11:22 UTC

NP-MRD ID

NP0038530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside is found in Spiraea canescens. 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside was first documented in 2009 (Choudhary, M.I., et al.). Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123113D          

 54 56  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123113D          

 54 56  0  0  0  0            999 V2000
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    1.6443   -2.3979    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4770   -2.6311    8.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -2.7509    7.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869   -2.8505    4.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -2.7223   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.3972   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -0.9394   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627    1.4204   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    4.2049   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    6.2651    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5994    9.2402    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    8.3151    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850    6.2700   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.9842   -3.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689    3.0382   -3.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -0.0618   -3.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.9778   -5.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225   -0.6457   -3.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -2.0391   -4.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 29  1  0  0  0  0
  4  5  1  0  0  0  0
 29 31  1  0  0  0  0
  5  6  2  0  0  0  0
 31 14  1  0  0  0  0
  6  7  1  0  0  0  0
 14 15  1  0  0  0  0
  7  8  2  0  0  0  0
 15 16  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  5  1  0  0  0  0
 31 32  1  0  0  0  0
  2  1  2  0  0  0  0
  2 12  1  0  0  0  0
 29 30  1  0  0  0  0
  8  9  1  0  0  0  0
 27 28  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 13 12  1  0  0  0  0
 20 21  2  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2  3  1  0  0  0  0
 23 25  1  0  0  0  0
 16 27  1  0  0  0  0
 25 26  2  0  0  0  0
 26 20  1  0  0  0  0
  3  4  2  0  0  0  0
 23 24  1  0  0  0  0
 14 13  1  0  0  0  0
 16 17  1  0  0  0  0
 16 43  1  1  0  0  0
 31 53  1  6  0  0  0
 32 54  1  0  0  0  0
 29 51  1  1  0  0  0
 30 52  1  0  0  0  0
 27 49  1  6  0  0  0
 28 50  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 14 42  1  1  0  0  0
  3 33  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
  9 37  1  0  0  0  0
 21 44  1  0  0  0  0
 22 45  1  0  0  0  0
 25 47  1  0  0  0  0
 26 48  1  0  0  0  0
 24 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038530

> <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(=O)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([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c23-14-6-1-12(2-7-14)3-10-17(25)30-11-16-18(26)19(27)20(28)22(31-16)32-21(29)13-4-8-15(24)9-5-13/h1-10,16,18-20,22-24,26-28H,11H2/b10-3+/t16-,18-,19+,20-,22+/m1/s1

> <INCHI_KEY>
APEWWGUQMHOMDD-UUEPMHOOSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.23266848473111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.9895207053333333

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.446240425876177

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.420761977409683

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491129541617244

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
109.27490000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    2.4990   -3.0520    0.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443   -2.3979    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101   -2.2602    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -2.8934    2.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.8056    4.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1223   -2.7711    5.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245   -2.7158    6.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -2.7052    7.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851   -2.6526    8.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396   -2.7541    6.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -2.8106    5.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536   -1.6767    0.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -1.7014   -1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848   -0.7182   -1.8274 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0232    0.6132   -1.4743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419    1.6160   -1.8134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3792    2.8705   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    3.8835   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439    3.8314   -1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    5.0910   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927    5.0954   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3852    6.2577    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    7.4081    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    8.5164    0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309    7.4206   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3265    6.2591   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039    1.6247   -3.3410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2842    2.4719   -3.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.2148   -3.8201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6216    0.1806   -5.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -0.8214   -3.3466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9897   -2.1208   -3.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -1.6244    2.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -3.4984    2.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.8003    4.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -2.6886    7.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770   -2.6311    8.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -2.7509    7.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869   -2.8505    4.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -2.7223   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.3972   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -0.9394   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627    1.4204   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    4.2049   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    6.2651    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5994    9.2402    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    8.3151    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850    6.2700   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.9842   -3.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689    3.0382   -3.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -0.0618   -3.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.9778   -5.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225   -0.6457   -3.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -2.0391   -4.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 29  1  0
  4  5  1  0
 29 31  1  0
  5  6  2  0
 31 14  1  0
  6  7  1  0
 14 15  1  0
  7  8  2  0
 15 16  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
 31 32  1  0
  2  1  2  0
  2 12  1  0
 29 30  1  0
  8  9  1  0
 27 28  1  0
 18 19  2  0
 18 20  1  0
 13 12  1  0
 20 21  2  0
 17 18  1  0
 21 22  1  0
 22 23  2  0
  2  3  1  0
 23 25  1  0
 16 27  1  0
 25 26  2  0
 26 20  1  0
  3  4  2  0
 23 24  1  0
 14 13  1  0
 16 17  1  0
 16 43  1  1
 31 53  1  6
 32 54  1  0
 29 51  1  1
 30 52  1  0
 27 49  1  6
 28 50  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
  3 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
 10 38  1  0
 11 39  1  0
  9 37  1  0
 21 44  1  0
 22 45  1  0
 25 47  1  0
 26 48  1  0
 24 46  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       2.499  -3.052   0.135  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.644  -2.398   0.708  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.510  -2.260   2.172  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.369  -2.893   2.985  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.328  -2.806   4.450  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.122  -2.771   5.167  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.125  -2.716   6.564  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.336  -2.705   7.247  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.385  -2.653   8.608  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.540  -2.754   6.556  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.536  -2.811   5.161  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.654  -1.677   0.129  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.674  -1.701  -1.311  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.385  -0.718  -1.827  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.023   0.613  -1.474  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.942   1.616  -1.813  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.379   2.870  -1.388  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.252   3.884  -1.207  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.444   3.831  -1.469  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.569   5.091  -0.673  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.793   5.095  -0.338  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.385   6.258   0.162  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.621   7.408   0.326  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.244   8.516   0.816  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.731   7.421  -0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.327   6.259  -0.500  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.204   1.625  -3.341  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.284   2.472  -3.774  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.555   0.215  -3.820  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.622   0.181  -5.256  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.539  -0.821  -3.347  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.990  -2.121  -3.733  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.713  -1.624   2.536  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.173  -3.498   2.567  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.167  -2.800   4.648  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.179  -2.689   7.096  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.477  -2.631   8.951  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.480  -2.751   7.101  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.487  -2.850   4.634  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.454  -2.722  -1.642  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.668  -1.397  -1.661  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.333  -0.939  -1.320  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.863   1.420  -1.248  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.406   4.205  -0.457  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.440   6.265   0.422  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.599   9.240   0.877  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.333   8.315   0.126  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.385   6.270  -0.754  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.310   1.984  -3.865  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.569   3.038  -3.025  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.561  -0.062  -3.477  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.135   0.978  -5.503  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.423  -0.646  -3.846  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.226  -2.039  -4.680  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   12    3                                                  
CONECT    3    2    4   33                                                  
CONECT    4    5    3   34                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   37                                                       
CONECT   10    8   11   38                                                  
CONECT   11   10    5   39                                                  
CONECT   12    2   13                                                       
CONECT   13   12   14   40   41                                             
CONECT   14   31   15   13   42                                             
CONECT   15   14   16                                                       
CONECT   16   15   27   17   43                                             
CONECT   17   18   16                                                       
CONECT   18   19   20   17                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   44                                                  
CONECT   22   21   23   45                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   46                                                       
CONECT   25   23   26   47                                                  
CONECT   26   25   20   48                                                  
CONECT   27   29   28   16   49                                             
CONECT   28   27   50                                                       
CONECT   29   27   31   30   51                                             
CONECT   30   29   52                                                       
CONECT   31   29   14   32   53                                             
CONECT   32   31   54                                                       
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   16                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   32                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

RDKit          3D

54 56  0  0  0  0  0  0  0  0999 V2000
    2.4990   -3.0520    0.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443   -2.3979    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101   -2.2602    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -2.8934    2.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.8056    4.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1223   -2.7711    5.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1245   -2.7158    6.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -2.7052    7.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851   -2.6526    8.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396   -2.7541    6.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -2.8106    5.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536   -1.6767    0.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -1.7014   -1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848   -0.7182   -1.8274 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0232    0.6132   -1.4743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9419    1.6160   -1.8134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3792    2.8705   -1.3879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    3.8835   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439    3.8314   -1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685    5.0910   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7927    5.0954   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3852    6.2577    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214    7.4081    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444    8.5164    0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309    7.4206   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3265    6.2591   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039    1.6247   -3.3410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2842    2.4719   -3.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.2148   -3.8201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6216    0.1806   -5.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -0.8214   -3.3466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9897   -2.1208   -3.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -1.6244    2.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -3.4984    2.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1673   -2.8003    4.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -2.6886    7.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770   -2.6311    8.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -2.7509    7.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869   -2.8505    4.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -2.7223   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.3972   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -0.9394   -1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627    1.4204   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    4.2049   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    6.2651    0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5994    9.2402    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    8.3151    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850    6.2700   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.9842   -3.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689    3.0382   -3.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -0.0618   -3.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    0.9778   -5.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4225   -0.6457   -3.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -2.0391   -4.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 29  1  0
  4  5  1  0
 29 31  1  0
  5  6  2  0
 31 14  1  0
  6  7  1  0
 14 15  1  0
  7  8  2  0
 15 16  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
 31 32  1  0
  2  1  2  0
  2 12  1  0
 29 30  1  0
  8  9  1  0
 27 28  1  0
 18 19  2  0
 18 20  1  0
 13 12  1  0
 20 21  2  0
 17 18  1  0
 21 22  1  0
 22 23  2  0
  2  3  1  0
 23 25  1  0
 16 27  1  0
 25 26  2  0
 26 20  1  0
  3  4  2  0
 23 24  1  0
 14 13  1  0
 16 17  1  0
 16 43  1  1
 31 53  1  6
 32 54  1  0
 29 51  1  1
 30 52  1  0
 27 49  1  6
 28 50  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
  3 33  1  0
  4 34  1  0
  6 35  1  0
  7 36  1  0
 10 38  1  0
 11 39  1  0
  9 37  1  0
 21 44  1  0
 22 45  1  0
 25 47  1  0
 26 48  1  0
 24 46  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoic acid	Generator

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl 4-hydroxybenzoate

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(=O)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([H])=C1[H]

InChI Identifier

InChI=1S/C22H22O10/c23-14-6-1-12(2-7-14)3-10-17(25)30-11-16-18(26)19(27)20(28)22(31-16)32-21(29)13-4-8-15(24)9-5-13/h1-10,16,18-20,22-24,26-28H,11H2/b10-3+/t16-,18-,19+,20-,22+/m1/s1

InChI Key

APEWWGUQMHOMDD-UUEPMHOOSA-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
Spiraea canescens	JEOL database	Choudhary, M.I., et al, Phytochemistry 70, 1467 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Monocyclic benzene moiety
Monosaccharide
Oxane
Dicarboxylic acid or derivatives
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.22	ALOGPS
logP	1.99	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.27 m³·mol⁻¹	ChemAxon
Polarizability	45.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

44514055

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Choudhary, M.I., et al. (2009). Choudhary, M.I., et al, Phytochemistry 70, 1467 (2009). Phytochem..

Showing NP-Card for 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside (NP0038530)

MOL for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

3D MOL for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

3D SDF for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

3D-SDF for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

PDB for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

3D PDB for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

SMILES for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

INCHI for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

Structure for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)

3D Structure for NP0038530 (6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside)