NP-MRD: Showing NP-Card for ent-1beta-hydroxy-9(11),16-kauradien-15-one (NP0026628)

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Record Information

Version

2.0

Created at

2021-06-19 18:28:04 UTC

Updated at

2021-06-29 23:52:17 UTC

NP-MRD ID

NP0026628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-1beta-hydroxy-9(11),16-kauradien-15-one

Provided By

JEOL Database JEOL Logo

Description

ent-1beta-hydroxy-9(11),16-kauradien-15-one is found in Jungermannia. ent-1beta-hydroxy-9(11),16-kauradien-15-one was first documented in 2003 (Nagashima, F., et al.). Based on a literature review very few articles have been published on 1alpha-Hydroxykaura-9(11),16-diene-15-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120283D          

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     RDKit          3D

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  Mrv1652306192120283D          

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  9 12  1  0  0  0  0
 16 14  1  0  0  0  0
 14 13  1  0  0  0  0
 19 20  1  0  0  0  0
 16 17  1  1  0  0  0
  5 22  1  0  0  0  0
 21  2  1  0  0  0  0
 21 20  1  0  0  0  0
  8 29  1  6  0  0  0
 13 12  1  0  0  0  0
 21 22  1  0  0  0  0
  5  3  1  6  0  0  0
  2  3  1  0  0  0  0
 19 18  2  0  0  0  0
  2  1  2  3  0  0  0
  5  6  1  0  0  0  0
  3  4  2  0  0  0  0
 18 16  1  0  0  0  0
  9 10  1  1  0  0  0
 16  8  1  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
  9 11  1  0  0  0  0
 14 40  1  6  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 21 48  1  1  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 15 41  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]34C(=O)C(=C([H])[H])[C@@]([H])(C3([H])[H])C([H])([H])C([H])=C4[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-12-13-5-6-15-19(4)14(18(2,3)9-8-16(19)21)7-10-20(15,11-13)17(12)22/h6,13-14,16,21H,1,5,7-11H2,2-4H3/t13-,14-,16+,19-,20-/m1/s1

> <INCHI_KEY>
IOZJOYCLUFVWGD-NTNYXWSSSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.77086187981524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,8S,9R,13R)-8-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-15-one

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.824398619666668

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5524606189701459

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.75689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,8S,9R,13R)-8-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-15-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -4.9928    0.5246    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6975    0.7805    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.0791    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391   -0.7451   -0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    0.5950    0.7231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1591   -0.4638    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737   -0.7926   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.2904   -1.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1846    0.0086   -2.9276 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7013   -0.0507   -2.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7965   -1.3592   -3.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880    1.0831   -3.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0467    2.4969   -3.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391    2.7740   -2.2710 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4161    4.1208   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    1.7588   -1.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6073    2.1052   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608    1.8627   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    2.9942    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    3.0742    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0418    1.7224    1.8534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7356    0.9745    2.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642    1.0416    1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   -0.2105   -0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6296   -0.1290    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -1.3924    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.0183   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -1.7271   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270    0.1588   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -0.2411   -3.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.8760   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652   -0.8602   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -2.1945   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821   -1.4224   -3.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022   -1.5146   -4.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    0.9482   -4.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    0.9630   -4.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    3.2052   -4.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    2.7077   -3.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041    2.7461   -2.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    4.7005   -2.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    2.9773    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    1.2899    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    2.3645   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196    3.9306   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    3.4903    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080    3.7841    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439    1.8615    2.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.5928    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    0.0796    2.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  8  9  1  0
  5 18  1  0
  9 12  1  0
 16 14  1  0
 14 13  1  0
 19 20  1  0
 16 17  1  1
  5 22  1  0
 21  2  1  0
 21 20  1  0
  8 29  1  6
 13 12  1  0
 21 22  1  0
  5  3  1  6
  2  3  1  0
 19 18  2  0
  2  1  2  3
  5  6  1  0
  3  4  2  0
 18 16  1  0
  9 10  1  1
 16  8  1  0
 14 15  1  0
  8  7  1  0
  9 11  1  0
 14 40  1  6
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  0
 22 50  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
  1 23  1  0
  1 24  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 15 41  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.993   0.525   0.675  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.697   0.781   0.875  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.576   0.079   0.164  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.739  -0.745  -0.722  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.245   0.595   0.723  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.159  -0.464   0.791  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.474  -0.793  -0.561  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.302   0.290  -1.655  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.185   0.009  -2.928  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.701  -0.051  -2.656  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.797  -1.359  -3.546  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.888   1.083  -3.995  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.047   2.497  -3.470  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.139   2.774  -2.271  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.416   4.121  -1.861  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.315   1.759  -1.080  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.607   2.105  -0.301  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.861   1.863  -0.053  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.560   2.994   0.205  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.701   3.074   1.197  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.042   1.722   1.853  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.736   0.975   2.145  0.00  0.00           C+0
HETATM   23  H   UNK     0      -5.764   1.042   1.234  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.307  -0.211  -0.062  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.630  -0.129   1.477  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.549  -1.392   1.228  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.530  -1.018  -0.385  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.026  -1.727  -0.922  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.727   0.159  -2.027  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.251  -0.241  -3.586  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.101   0.876  -2.247  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.965  -0.860  -1.969  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.078  -2.195  -2.897  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.282  -1.422  -3.729  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.302  -1.515  -4.507  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.542   0.948  -4.865  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.139   0.963  -4.365  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.805   3.205  -4.273  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.093   2.708  -3.220  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.904   2.746  -2.613  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.215   4.700  -2.616  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.460   2.977   0.348  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.953   1.290   0.339  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.435   2.365  -0.965  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.320   3.931  -0.289  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.584   3.490   0.699  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.408   3.784   1.981  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.644   1.861   2.757  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.012   1.593   2.690  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.932   0.080   2.753  0.00  0.00           H+0
CONECT    1    2   23   24                                                  
CONECT    2   21    3    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   18   22    3    6                                             
CONECT    6    7    5   25   26                                             
CONECT    7    6    8   27   28                                             
CONECT    8    9   29   16    7                                             
CONECT    9    8   12   10   11                                             
CONECT   10    9   30   31   32                                             
CONECT   11    9   33   34   35                                             
CONECT   12    9   13   36   37                                             
CONECT   13   14   12   38   39                                             
CONECT   14   16   13   15   40                                             
CONECT   15   14   41                                                       
CONECT   16   14   17   18    8                                             
CONECT   17   16   42   43   44                                             
CONECT   18    5   19   16                                                  
CONECT   19   20   18   45                                                  
CONECT   20   19   21   46   47                                             
CONECT   21    2   20   22   48                                             
CONECT   22    5   21   49   50                                             
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    6                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
   -4.9928    0.5246    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6975    0.7805    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.0791    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391   -0.7451   -0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    0.5950    0.7231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1591   -0.4638    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737   -0.7926   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.2904   -1.6551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1846    0.0086   -2.9276 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7013   -0.0507   -2.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7965   -1.3592   -3.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8880    1.0831   -3.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0467    2.4969   -3.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391    2.7740   -2.2710 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4161    4.1208   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145    1.7588   -1.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6073    2.1052   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608    1.8627   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    2.9942    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    3.0742    1.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0418    1.7224    1.8534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7356    0.9745    2.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642    1.0416    1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   -0.2105   -0.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6296   -0.1290    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -1.3924    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.0183   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -1.7271   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7270    0.1588   -2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -0.2411   -3.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.8760   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652   -0.8602   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -2.1945   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821   -1.4224   -3.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022   -1.5146   -4.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    0.9482   -4.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    0.9630   -4.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    3.2052   -4.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    2.7077   -3.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041    2.7461   -2.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145    4.7005   -2.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    2.9773    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9526    1.2899    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    2.3645   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196    3.9306   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    3.4903    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080    3.7841    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439    1.8615    2.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    1.5928    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    0.0796    2.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  8  9  1  0
  5 18  1  0
  9 12  1  0
 16 14  1  0
 14 13  1  0
 19 20  1  0
 16 17  1  1
  5 22  1  0
 21  2  1  0
 21 20  1  0
  8 29  1  6
 13 12  1  0
 21 22  1  0
  5  3  1  6
  2  3  1  0
 19 18  2  0
  2  1  2  3
  5  6  1  0
  3  4  2  0
 18 16  1  0
  9 10  1  1
 16  8  1  0
 14 15  1  0
  8  7  1  0
  9 11  1  0
 14 40  1  6
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  0
 22 50  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
  1 23  1  0
  1 24  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 15 41  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
1a-Hydroxykaura-9(11),16-diene-15-one	Generator
1Α-hydroxykaura-9(11),16-diene-15-one	Generator

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

(1R,4R,8S,9R,13R)-8-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-15-one

Traditional Name

(1R,4R,8S,9R,13R)-8-hydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-15-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]34C(=O)C(=C([H])[H])[C@@]([H])(C3([H])[H])C([H])([H])C([H])=C4[C@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C20H28O2/c1-12-13-5-6-15-19(4)14(18(2,3)9-8-16(19)21)7-10-20(15,11-13)17(12)22/h6,13-14,16,21H,1,5,7-11H2,2-4H3/t13-,14-,16+,19-,20-/m1/s1

InChI Key

IOZJOYCLUFVWGD-NTNYXWSSSA-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, 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
Jungermannia	JEOL database	Nagashima, F., et al, Chem. Pharm. Bull. 51, 1189 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	3.65	ALOGPS
logP	3.82	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.76 m³·mol⁻¹	ChemAxon
Polarizability	34.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9956250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11781569

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nagashima, F., et al. (2003). Nagashima, F., et al, Chem. Pharm. Bull. 51, 1189 (2003). Chem. Pharm. Bull..

Showing NP-Card for ent-1beta-hydroxy-9(11),16-kauradien-15-one (NP0026628)

MOL for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

3D MOL for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

3D SDF for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

3D-SDF for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

PDB for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

3D PDB for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

SMILES for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

INCHI for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

Structure for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)

3D Structure for NP0026628 (ent-1beta-hydroxy-9(11),16-kauradien-15-one)