NP-MRD: Showing NP-Card for (1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0165189)

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Record Information

Version

2.0

Created at

2022-09-03 00:14:49 UTC

Updated at

2022-09-03 00:14:50 UTC

NP-MRD ID

NP0165189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

Description

Coccinone G belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione is found in Moronobea coccinea. Based on a literature review very few articles have been published on Coccinone G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202142D          

 44 46  0  0  1  0            999 V2000
   -1.2831   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456    0.2293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0323   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3477   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0954    0.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0049    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    1.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  2  4  1  0  0  0  0
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  6  5  1  1  0  0  0
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 29 42  1  0  0  0  0
  6 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

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   -1.5173    1.3161    0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857    0.3201   -0.8332 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032202142D          

 44 46  0  0  1  0            999 V2000
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   -0.0456   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2831   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456    0.2293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2701   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.8486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0323   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -2.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -1.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779    1.5749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323    1.3072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0323    2.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    2.5447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4612    2.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    2.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    2.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    1.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    2.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    3.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323    3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954    0.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    1.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 29 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  2  0  0  0  0
 29 42  1  0  0  0  0
  6 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@@H](C[C@@]12C(=O)C(=C(O)C3=CC=C(O)C(O)=C3)C(=O)[C@@](CCC(C)=C)(C[C@@H](CCC(C)=C)C1(C)C)C2=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-38-34(43)31(32(41)26-14-16-29(39)30(40)19-26)33(42)37(35(38)44,18-17-24(5)6)21-28(36(38,9)10)15-12-23(3)4/h11,14,16,19,27-28,39-41H,3,5,7,12-13,15,17-18,20-21H2,1-2,4,6,8-10H3/t27-,28+,37+,38-/m0/s1

> <INCHI_KEY>
WGOHAYATHRNCBR-SMDXAGPFSA-N

> <FORMULA>
C38H50O6

> <MOLECULAR_WEIGHT>
602.812

> <EXACT_MASS>
602.36073933

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
67.59246812193399

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
9.733662763333331

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.51169486921832

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.96406103760224

> <JCHEM_PKA_STRONGEST_BASIC>
-6.319325089807994

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
178.34570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.395  -3.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.625  -2.239   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.085  -2.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.395  -0.906   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.625   0.428   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.085   0.428   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.504  -0.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.927  -1.584   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.927  -3.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.593  -3.894   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.593  -5.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.927  -6.204   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.740  -6.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.350  -0.995   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.439  -2.084   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.939   0.428   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.479   0.428   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.249   1.762   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.249  -0.906   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.789  -0.906   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.559  -2.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.789  -3.573   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.559  -4.907   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.249  -3.573   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.479  -4.907   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.479  -2.239   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.350   1.851   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.439   2.940   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.927   2.440   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.927   3.980   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.261   4.750   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.594   3.980   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.928   4.750   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.262   3.980   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.262   2.440   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.595   4.750   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.261   6.290   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.594   7.060   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.927   7.060   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.424   0.428   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.178   1.333   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.504   1.851   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.009   3.309   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.954   2.346   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14   40                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19                                                       
CONECT   27   16   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   40   42                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   31   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   29    8   41                                                  
CONECT   41   40                                                            
CONECT   42   29    6   43   44                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₅₀O₆

Average Mass

602.8120 Da

Monoisotopic Mass

602.36074 Da

IUPAC Name

(1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

Traditional Name

(1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@@H](C[C@@]12C(=O)C(=C(O)C3=CC=C(O)C(O)=C3)C(=O)[C@@](CCC(C)=C)(C[C@@H](CCC(C)=C)C1(C)C)C2=O)C(C)=C

InChI Identifier

InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-38-34(43)31(32(41)26-14-16-29(39)30(40)19-26)33(42)37(35(38)44,18-17-24(5)6)21-28(36(38,9)10)15-12-23(3)4/h11,14,16,19,27-28,39-41H,3,5,7,12-13,15,17-18,20-21H2,1-2,4,6,8-10H3/t27-,28+,37+,38-/m0/s1

InChI Key

WGOHAYATHRNCBR-SMDXAGPFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Moronobea coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Enol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.35	ALOGPS
logP	9.73	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	5.96	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	178.35 m³·mol⁻¹	ChemAxon
Polarizability	67.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

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KNApSAcK ID

C00048359

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PubChem Compound

102283887

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References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione (NP0165189)

MOL for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D MOL for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D SDF for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D-SDF for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

PDB for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D PDB for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

SMILES for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

INCHI for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

Structure for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)

3D Structure for NP0165189 ((1s,5r,7r)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-5-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-1,7-bis(3-methylbut-3-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione)