NP-MRD: Showing NP-Card for 1beta-p-hydroxy-E-cinnamoyldrimeninol (NP0043345)

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Record Information

Version

1.0

Created at

2021-06-21 00:46:43 UTC

Updated at

2021-06-30 00:18:58 UTC

NP-MRD ID

NP0043345

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta-p-hydroxy-E-cinnamoyldrimeninol

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2333574 belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 1beta-p-hydroxy-E-cinnamoyldrimeninol is found in Zygogynum calothyrsum. It was first documented in 2013 (Devkota, K. P., et al.). Based on a literature review very few articles have been published on CHEMBL2333574.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102463D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102463D          

 59 62  0  0  0  0            999 V2000
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    0.5520   -2.1414   -2.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -1.2965   -1.4804 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3816   -0.4029   -1.3608 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9154   -3.1791    4.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -2.6807    5.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2627   -1.5331    4.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273   -1.9300    4.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -2.6272    3.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -0.2064    3.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474   -0.1818    3.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8446    2.4290   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    2.6442   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    4.0005   -2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1864    6.1644   -3.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533    8.0604   -3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    7.0320   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402    4.8711   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762   -1.4948    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5997   -0.7591    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -0.0169    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8652   -2.7524   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716   -4.8388   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255   -5.0820    2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -3.6931    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -3.7294    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845   -4.1339   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230   -2.9850   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.7209   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    0.1272   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  2  1  1  1  0  0  0
 19 21  1  0  0  0  0
 19 20  1  6  0  0  0
 25 24  1  0  0  0  0
 28 29  1  0  0  0  0
 24 23  1  0  0  0  0
 21 51  1  6  0  0  0
 23 22  2  0  0  0  0
 21 22  1  0  0  0  0
 14 15  2  0  0  0  0
  2 25  1  0  0  0  0
 15 17  1  0  0  0  0
 19  6  1  0  0  0  0
 17 18  2  0  0  0  0
 19 25  1  0  0  0  0
 18 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  5  4  1  0  0  0  0
 12 11  1  0  0  0  0
 22 26  1  0  0  0  0
 11 10  2  0  0  0  0
 26 27  1  0  0  0  0
 10  8  1  0  0  0  0
 27 28  1  0  0  0  0
 15 16  1  0  0  0  0
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  8  9  2  0  0  0  0
  8  7  1  0  0  0  0
  5  6  1  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
 25 55  1  6  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  4 36  1  0  0  0  0
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  6 40  1  6  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 20 48  1  0  0  0  0
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 20 50  1  0  0  0  0
 29 59  1  0  0  0  0
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 16 45  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043345

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])=C4C([H])([H])O[C@]([H])(O[H])[C@]4([H])[C@@]23C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O5/c1-23(2)13-12-19(29-20(26)11-6-15-4-8-17(25)9-5-15)24(3)18(23)10-7-16-14-28-22(27)21(16)24/h4-9,11,18-19,21-22,25,27H,10,12-14H2,1-3H3/b11-6+/t18-,19+,21+,22-,24+/m0/s1

> <INCHI_KEY>
VCKBZSACDFEBME-ZLZPLZGWSA-N

> <FORMULA>
C24H30O5

> <MOLECULAR_WEIGHT>
398.499

> <EXACT_MASS>
398.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.53476216335224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5aS,9R,9aS,9bS)-1-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-9-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
4.265580841333332

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.09521935149948

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397740012543528

> <JCHEM_PKA_STRONGEST_BASIC>
-4.069733435500226

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
111.8145

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5aS,9R,9aS,9bS)-1-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-9-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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    0.1138   -2.2720   -0.3129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1192   -3.3250   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143   -4.1275    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025   -4.0593    1.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702   -3.1724    2.0224 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5520   -2.1414   -2.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -1.2965   -1.4804 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.9244    2.6442   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    4.0005   -2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1864    6.1644   -3.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533    8.0604   -3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5997   -0.7591    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8652   -2.7524   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2255   -5.0820    2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0845   -4.1339   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230   -2.9850   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.7209   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    0.1272   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  1  1  1
 19 21  1  0
 19 20  1  6
 25 24  1  0
 28 29  1  0
 24 23  1  0
 21 51  1  6
 23 22  2  0
 21 22  1  0
 14 15  2  0
  2 25  1  0
 15 17  1  0
 19  6  1  0
 17 18  2  0
 19 25  1  0
 18 12  1  0
 12 13  2  0
 13 14  1  0
  5  4  1  0
 12 11  1  0
 22 26  1  0
 11 10  2  0
 26 27  1  0
 10  8  1  0
 27 28  1  0
 15 16  1  0
 28 21  1  0
  8  9  2  0
  8  7  1  0
  5  6  1  0
  2  3  1  0
  6  7  1  0
 25 55  1  6
  5 38  1  0
  5 39  1  0
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  4 37  1  0
  6 40  1  6
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 24 54  1  0
 23 52  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 29 59  1  0
 14 44  1  0
 17 46  1  0
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 13 43  1  0
 11 42  1  0
 10 41  1  0
 16 45  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.560  -4.456   4.096  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.156  -3.058   3.557  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.011  -2.583   4.444  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.373  -2.122   3.763  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.262  -0.791   3.029  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.087  -1.000   1.522  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.016   0.284   0.872  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.195   0.880   0.571  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.311   0.436   0.775  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.890   2.173  -0.073  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.890   2.961  -0.496  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.689   4.255  -1.164  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.604   4.652  -2.150  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.469   5.885  -2.797  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.420   6.727  -2.447  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.248   7.937  -3.050  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.512   6.360  -1.462  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.649   5.128  -0.817  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.190  -1.825   1.188  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.465  -0.990   1.459  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.114  -2.272  -0.313  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.119  -3.325  -0.678  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.714  -4.128   0.216  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.403  -4.059   1.688  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.170  -3.172   2.022  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.377  -3.227  -2.143  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.552  -2.141  -2.611  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.296  -1.297  -1.480  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.382  -0.403  -1.361  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.363  -4.899   3.497  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.286  -5.152   4.093  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.922  -4.391   5.129  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.915  -3.179   4.291  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.750  -2.681   5.506  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.263  -1.533   4.301  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.527  -1.930   4.832  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.284  -2.627   3.413  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.171  -0.206   3.216  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.447  -0.182   3.435  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.961  -1.550   1.144  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.845   2.429  -0.192  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.924   2.644  -0.374  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.430   4.000  -2.429  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.186   6.164  -3.561  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.953   8.060  -3.706  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.703   7.032  -1.191  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.940   4.871  -0.034  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.376  -1.495   1.123  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.600  -0.759   2.513  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.434  -0.017   0.962  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.865  -2.752  -0.474  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.472  -4.839  -0.104  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.226  -5.082   2.038  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.298  -3.693   2.200  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.693  -3.729   1.617  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.085  -4.134  -2.678  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.423  -2.985  -2.357  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.616  -0.721  -1.667  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.352   0.127  -2.174  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    4    1   25    3                                             
CONECT    3    2   33   34   35                                             
CONECT    4    2    5   36   37                                             
CONECT    5    4    6   38   39                                             
CONECT    6   19    5    7   40                                             
CONECT    7    8    6                                                       
CONECT    8   10    9    7                                                  
CONECT    9    8                                                            
CONECT   10   11    8   41                                                  
CONECT   11   12   10   42                                                  
CONECT   12   18   13   11                                                  
CONECT   13   12   14   43                                                  
CONECT   14   15   13   44                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   45                                                       
CONECT   17   15   18   46                                                  
CONECT   18   17   12   47                                                  
CONECT   19   21   20    6   25                                             
CONECT   20   19   48   49   50                                             
CONECT   21   19   51   22   28                                             
CONECT   22   23   21   26                                                  
CONECT   23   24   22   52                                                  
CONECT   24   25   23   53   54                                             
CONECT   25   24    2   19   55                                             
CONECT   26   22   27   56   57                                             
CONECT   27   26   28                                                       
CONECT   28   29   27   21   58                                             
CONECT   29   28   59                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
   -0.5599   -4.4562    4.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562   -3.0580    3.5569 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0114   -2.5831    4.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -2.1224    3.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -0.7912    3.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872   -1.0002    1.5223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0157    0.2840    0.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1948    0.8798    0.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    0.4356    0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8901    2.1732   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    2.9614   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895    4.2545   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6043    4.6524   -2.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685    5.8846   -2.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197    6.7270   -2.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2480    7.9372   -3.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123    6.3596   -1.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494    5.1278   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896   -1.8253    1.1882 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4653   -0.9904    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -2.2720   -0.3129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1192   -3.3250   -0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7143   -4.1275    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025   -4.0593    1.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1702   -3.1724    2.0224 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3773   -3.2270   -2.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.1414   -2.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -1.2965   -1.4804 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3816   -0.4029   -1.3608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3634   -4.8995    3.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857   -5.1516    4.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217   -4.3912    5.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -3.1791    4.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -2.6807    5.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2627   -1.5331    4.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273   -1.9300    4.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -2.6272    3.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -0.2064    3.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474   -0.1818    3.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -1.5496    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446    2.4290   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    2.6442   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    4.0005   -2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1864    6.1644   -3.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533    8.0604   -3.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    7.0320   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402    4.8711   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762   -1.4948    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5997   -0.7591    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -0.0169    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8652   -2.7524   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716   -4.8388   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255   -5.0820    2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -3.6931    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -3.7294    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845   -4.1339   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230   -2.9850   -2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160   -0.7209   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517    0.1272   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  1  1  1
 19 21  1  0
 19 20  1  6
 25 24  1  0
 28 29  1  0
 24 23  1  0
 21 51  1  6
 23 22  2  0
 21 22  1  0
 14 15  2  0
  2 25  1  0
 15 17  1  0
 19  6  1  0
 17 18  2  0
 19 25  1  0
 18 12  1  0
 12 13  2  0
 13 14  1  0
  5  4  1  0
 12 11  1  0
 22 26  1  0
 11 10  2  0
 26 27  1  0
 10  8  1  0
 27 28  1  0
 15 16  1  0
 28 21  1  0
  8  9  2  0
  8  7  1  0
  5  6  1  0
  2  3  1  0
  6  7  1  0
 25 55  1  6
  5 38  1  0
  5 39  1  0
  4 36  1  0
  4 37  1  0
  6 40  1  6
 24 53  1  0
 24 54  1  0
 23 52  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  6
  1 30  1  0
  1 31  1  0
  1 32  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 29 59  1  0
 14 44  1  0
 17 46  1  0
 18 47  1  0
 13 43  1  0
 11 42  1  0
 10 41  1  0
 16 45  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₅

Average Mass

398.4990 Da

Monoisotopic Mass

398.20932 Da

IUPAC Name

(1S,5aS,9R,9aS,9bS)-1-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-9-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(1S,5aS,9R,9aS,9bS)-1-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-9-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])=C4C([H])([H])O[C@]([H])(O[H])[C@]4([H])[C@@]23C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C24H30O5/c1-23(2)13-12-19(29-20(26)11-6-15-4-8-17(25)9-5-15)24(3)18(23)10-7-16-14-28-22(27)21(16)24/h4-9,11,18-19,21-22,25,27H,10,12-14H2,1-3H3/b11-6+/t18-,19+,21+,22-,24+/m0/s1

InChI Key

VCKBZSACDFEBME-ZLZPLZGWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zygogynum calothyrsum	JEOL database	Devkota, K. P., et al, J. Nat. Prod. 76, 710 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Coumaric acid ester
Naphthofuran
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Hemiacetal
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	4.16	ALOGPS
logP	4.27	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.81 m³·mol⁻¹	ChemAxon
Polarizability	44.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

29355667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71665803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Devkota, K. P., et al. (2013). Devkota, K. P., et al, J. Nat. Prod. 76, 710 (2013). J. Nat. Prod..

Showing NP-Card for 1beta-p-hydroxy-E-cinnamoyldrimeninol (NP0043345)

MOL for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

3D MOL for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

3D SDF for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

3D-SDF for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

PDB for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

3D PDB for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

SMILES for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

INCHI for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

Structure for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)

3D Structure for NP0043345 (1beta-p-hydroxy-E-cinnamoyldrimeninol)