NP-MRD: Showing NP-Card for totarol (NP0040648)

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Record Information

Version

2.0

Created at

2021-06-20 22:45:16 UTC

Updated at

2021-06-30 00:14:40 UTC

NP-MRD ID

NP0040648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

totarol

Provided By

JEOL Database JEOL Logo

Description

totarol is found in Afrocarpus gracilior, Apis mellifera, Biota orientalis, Callitropsis nootkatensis, Chamaecyparis formosensis, Chamaecyparis pisifera, Cryptomeria japonica, Cupressus sempervirens, Dacrycarpus vieillardii, Juniperus chinensis, Juniperus communis, Juniperus formosana, Juniperus phoenicea, Juniperus rigida, Nageia nagi, Platycladus orientalis, Podocarpus gnidioides, Podocarpus macrophyllus , Podocarpus sylvestris, Podocarpus totara, Podocarpus totara L. , Retrophyllum comptonii, Retrophyllum minus, Schistochila acuminata, Tetraclinis articulata, Thuja occidentalis, Thuja plicata, Thuja standishii and Thujopsis dolabrata. totarol was first documented in 2021 (PMID: 34227213). Based on a literature review a small amount of articles have been published on (+)-totarol (PMID: 33568294) (PMID: 34299601) (PMID: 34298240) (PMID: 34077024).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306212100453D          

 51 53  0  0  0  0            999 V2000
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    5.2784   -1.3470   -0.3932 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv1652306212100453D          

 51 53  0  0  0  0            999 V2000
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   -1.1729    2.3655    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    1.7425    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    0.0789    2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297    0.3317    3.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705    1.5617    2.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -2.6527    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -1.8841    2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063   -2.0668    3.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 13  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  2  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 17 14  1  0  0  0  0
 20 21  1  1  0  0  0
 20  9  1  0  0  0  0
 14 15  1  6  0  0  0
 13 12  1  0  0  0  0
 14 16  1  0  0  0  0
 12 11  1  0  0  0  0
 13 36  1  6  0  0  0
 11 10  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
  4  2  1  0  0  0  0
 14 13  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  1  0  0  0  0
  2  3  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
  6 29  1  0  0  0  0
  2 25  1  6  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(=C1C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1

> <INCHI_KEY>
ZRVDANDJSTYELM-FXAWDEMLSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.459

> <EXACT_MASS>
286.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.44705297771703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.253506807333332

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.767814295710068

> <JCHEM_PKA_STRONGEST_BASIC>
-5.204691040030707

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
89.7077

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
totarol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    6.3201   -0.2531   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -1.3470   -0.3932 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9249   -2.7338   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960   -1.0507    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -0.9058    2.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3213   -1.0552    2.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -0.6209    3.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8238   -0.4677    3.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847   -0.5935    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755   -0.9165    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -1.0844   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034   -1.0538   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596   -0.0214    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2310    0.3988    0.0244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2229   -0.7772   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.1410   -1.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819    1.4048    1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    0.9470    2.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.6337    2.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -0.4529    1.7490 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0927   -1.8330    2.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -0.4230   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082   -0.2236    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.7351   -0.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6643   -1.3622   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -2.9653   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673   -3.5086   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6590   -2.8108    0.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -0.9223    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470   -0.5182    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.2643    3.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -2.0370   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949   -0.2714   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064   -0.8304   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045   -2.0514   -0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.9040    0.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -1.2589    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -1.5409   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067   -0.4295   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618    0.4703   -2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.5816   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    1.9565   -1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    1.6115    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    2.3655    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    1.7425    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    0.0789    2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297    0.3317    3.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705    1.5617    2.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -2.6527    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -1.8841    2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063   -2.0668    3.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 13  1  0
  9  8  2  0
 10  4  2  0
  5  7  2  0
  7  8  1  0
  5  4  1  0
 18 17  1  0
 18 19  1  0
 17 14  1  0
 20 21  1  1
 20  9  1  0
 14 15  1  6
 13 12  1  0
 14 16  1  0
 12 11  1  0
 13 36  1  6
 11 10  1  0
  5  6  1  0
  9 10  1  0
  4  2  1  0
 14 13  1  0
  2  1  1  0
 20 19  1  0
  2  3  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 19 47  1  0
 19 48  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
 11 33  1  0
  7 30  1  0
  8 31  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
  6 29  1  0
  2 25  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 26  1  0
  3 27  1  0
  3 28  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       6.320  -0.253  -0.659  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.278  -1.347  -0.393  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.925  -2.734  -0.316  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.396  -1.051   0.825  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.971  -0.906   2.100  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.321  -1.055   2.260  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.199  -0.621   3.219  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.824  -0.468   3.088  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.185  -0.594   1.841  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.975  -0.917   0.703  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.328  -1.084  -0.659  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.803  -1.054  -0.705  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.260  -0.021   0.287  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.231   0.399   0.024  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.223  -0.777  -0.054  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.331   1.141  -1.336  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.682   1.405   1.109  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.385   0.947   2.528  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.096   0.634   2.720  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.640  -0.453   1.749  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.093  -1.833   2.191  0.00  0.00           C+0
HETATM   22  H   UNK     0       6.810  -0.423  -1.624  0.00  0.00           H+0
HETATM   23  H   UNK     0       7.108  -0.224   0.099  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.848   0.735  -0.693  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.664  -1.362  -1.297  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.445  -2.965  -1.252  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.167  -3.509  -0.154  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.659  -2.811   0.492  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.546  -0.922   3.194  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.647  -0.518   4.202  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.257  -0.264   3.992  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.644  -2.037  -1.100  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.695  -0.271  -1.299  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.506  -0.830  -1.734  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.405  -2.051  -0.494  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.832   0.904   0.101  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.394  -1.259   0.908  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.894  -1.541  -0.765  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.207  -0.430  -0.393  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.162   0.470  -2.184  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.326   1.582  -1.471  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.602   1.956  -1.401  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.756   1.611   1.015  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.173   2.365   0.950  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.673   1.742   3.226  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.000   0.079   2.788  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.230   0.332   3.766  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.671   1.562   2.592  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.465  -2.653   1.567  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.994  -1.884   2.195  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.406  -2.067   3.217  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    4    1    3   25                                             
CONECT    3    2   26   27   28                                             
CONECT    4   10    5    2                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   29                                                       
CONECT    7    5    8   30                                                  
CONECT    8    9    7   31                                                  
CONECT    9    8   20   10                                                  
CONECT   10    4   11    9                                                  
CONECT   11   12   10   32   33                                             
CONECT   12   13   11   34   35                                             
CONECT   13   20   12   36   14                                             
CONECT   14   17   15   16   13                                             
CONECT   15   14   37   38   39                                             
CONECT   16   14   40   41   42                                             
CONECT   17   18   14   43   44                                             
CONECT   18   17   19   45   46                                             
CONECT   19   18   20   47   48                                             
CONECT   20   13   21    9   19                                             
CONECT   21   20   49   50   51                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
    6.3201   -0.2531   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784   -1.3470   -0.3932 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9249   -2.7338   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960   -1.0507    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -0.9058    2.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3213   -1.0552    2.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -0.6209    3.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8238   -0.4677    3.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847   -0.5935    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755   -0.9165    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -1.0844   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034   -1.0538   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596   -0.0214    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2310    0.3988    0.0244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2229   -0.7772   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.1410   -1.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819    1.4048    1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3852    0.9470    2.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.6337    2.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -0.4529    1.7490 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0927   -1.8330    2.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -0.4230   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082   -0.2236    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    0.7351   -0.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6643   -1.3622   -1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -2.9653   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1673   -3.5086   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6590   -2.8108    0.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -0.9223    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470   -0.5182    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.2643    3.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -2.0370   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949   -0.2714   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064   -0.8304   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045   -2.0514   -0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.9040    0.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -1.2589    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -1.5409   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067   -0.4295   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618    0.4703   -2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.5816   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    1.9565   -1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    1.6115    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    2.3655    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    1.7425    3.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    0.0789    2.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297    0.3317    3.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6705    1.5617    2.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -2.6527    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942   -1.8841    2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063   -2.0668    3.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 13  1  0
  9  8  2  0
 10  4  2  0
  5  7  2  0
  7  8  1  0
  5  4  1  0
 18 17  1  0
 18 19  1  0
 17 14  1  0
 20 21  1  1
 20  9  1  0
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 13 12  1  0
 14 16  1  0
 12 11  1  0
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  5  6  1  0
  9 10  1  0
  4  2  1  0
 14 13  1  0
  2  1  1  0
 20 19  1  0
  2  3  1  0
 18 45  1  0
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 17 43  1  0
 17 44  1  0
 19 47  1  0
 19 48  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
 11 33  1  0
  7 30  1  0
  8 31  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
  6 29  1  0
  2 25  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
M  END

View in JSmol

Synonyms

Value	Source
4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol	MeSH
14-Isopropylpodocarpa-8,11,13-trien-13-ol	MeSH

Chemical Formula

C₂₀H₃₀O

Average Mass

286.4590 Da

Monoisotopic Mass

286.22967 Da

IUPAC Name

(4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol

Traditional Name

totarol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C(=C1C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1

InChI Key

ZRVDANDJSTYELM-FXAWDEMLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Afrocarpus gracilior	LOTUS Database	35616633
Apis mellifera	LOTUS Database	35616633
Biota orientalis	JEOL database	Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011)
Callitropsis nootkatensis	LOTUS Database	35616633
Chamaecyparis formosensis	Plant	KNApSAcK
Chamaecyparis pisifera	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cupressus sempervirens	LOTUS Database	35616633
Dacrycarpus vieillardii	Plant	KNApSAcK
Juniperus chinensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Juniperus formosana	LOTUS Database	35616633
Juniperus phoenicea	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Nageia nagi	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Podocarpus gnidioides	Plant	KNApSAcK
Podocarpus macrophyllus	Plant	KNApSAcK
Podocarpus sylvestris	Plant	KNApSAcK
Podocarpus totara	LOTUS Database	35616633
Podocarpus totara L.	Plant	KNApSAcK
Retrophyllum comptonii	Plant	KNApSAcK
Retrophyllum minus	LOTUS Database	35616633
Schistochila acuminata	LOTUS Database	35616633
Tetraclinis articulata	Plant	KNApSAcK
Thuja occidentalis	LOTUS Database	35616633
Thuja plicata	LOTUS Database	35616633
Thuja standishii	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	6.62	ALOGPS
logP	6.25	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	10.77	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.71 m³·mol⁻¹	ChemAxon
Polarizability	35.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

83757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ribeiro VP, Arruda C, Aldana-Mejia JA, Bastos JK, Tripathi SK, Khan SI, Khan IA, Ali Z: Phytochemical, Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees. Chem Biodivers. 2021 Jul 5. doi: 10.1002/cbdv.202100288. [PubMed:34227213 ]
Ma LT, Wang CH, Hon CY, Lee YR, Chu FH: Discovery and characterization of diterpene synthases in Chamaecyparis formosensis Matsum. which participated in an unprecedented diterpenoid biosynthesis route in conifer. Plant Sci. 2021 Mar;304:110790. doi: 10.1016/j.plantsci.2020.110790. Epub 2020 Dec 9. [PubMed:33568294 ]
Kim C, Le D, Lee M: Diterpenoids Isolated from Podocarpus macrophyllus Inhibited the Inflammatory Mediators in LPS-Induced HT-29 and RAW 264.7 Cells. Molecules. 2021 Jul 17;26(14). pii: molecules26144326. doi: 10.3390/molecules26144326. [PubMed:34299601 ]
Laamari Y, Oubella A, Bimoussa A, El Mansouri AE, Ketatni EM, Mentre O, Ait Itto MY, Morjani H, Khouili M, Auhmani A: Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol. Bioorg Chem. 2021 Oct;115:105165. doi: 10.1016/j.bioorg.2021.105165. Epub 2021 Jul 14. [PubMed:34298240 ]
Xu T, Huang L, Liu Z, Ma D, Zhang G, Ning X, Lu X, Liu H, Jiang B: Totarol, a natural diterpenoid, induces selective antitumor activity in SGC-7901 human gastric carcinoma cells by triggering apoptosis, cell cycle disruption and suppression of cancer cell migration. J BUON. 2021 Mar-Apr;26(2):640. [PubMed:34077024 ]
Zaugg, J., et al. (2011). Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011). J. Nat. Prod..

Showing NP-Card for totarol (NP0040648)

MOL for NP0040648 (totarol)

3D MOL for NP0040648 (totarol)

3D SDF for NP0040648 (totarol)

3D-SDF for NP0040648 (totarol)

PDB for NP0040648 (totarol)

3D PDB for NP0040648 (totarol)

SMILES for NP0040648 (totarol)

INCHI for NP0040648 (totarol)

Structure for NP0040648 (totarol)

3D Structure for NP0040648 (totarol)