NP-MRD: Showing NP-Card for Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene (NP0027481)

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Record Information

Version

2.0

Created at

2021-06-19 19:37:36 UTC

Updated at

2021-06-29 23:53:37 UTC

NP-MRD ID

NP0027481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene

Provided By

JEOL Database JEOL Logo

Description

Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene is found in Siegesbeckia orientalis. Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene was first documented in 2004 (Xiang, Y., et al.). Based on a literature review very few articles have been published on 15-keto-kirenol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121373D          

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     RDKit          3D

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M  END


  Mrv1652306192121373D          

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   -0.5960   -1.1371   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -0.3932   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.7757   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9099   -1.4163    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0453   -0.2684    3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533   -1.8537    3.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.3732    3.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -2.3339    2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -0.8335    3.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2651   -3.0337    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -3.4487    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -4.2739    2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994    2.0236    0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692    1.5986   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766    2.8131   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430    3.8694   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328    3.7775   -3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 22  1  0  0  0  0
 11 10  1  0  0  0  0
 18 20  1  0  0  0  0
 10  9  1  0  0  0  0
 11 36  1  1  0  0  0
 24  2  1  0  0  0  0
  9  8  1  0  0  0  0
 22  8  1  0  0  0  0
 18 11  1  0  0  0  0
 12 14  1  0  0  0  0
  2  3  1  6  0  0  0
  3  5  1  0  0  0  0
 12 11  1  0  0  0  0
  3  4  2  0  0  0  0
  2  7  1  0  0  0  0
  2  1  1  0  0  0  0
 22 23  1  0  0  0  0
 15 16  1  0  0  0  0
  8  7  2  0  0  0  0
 20 21  1  0  0  0  0
 24 23  1  0  0  0  0
 12 13  1  6  0  0  0
 15 17  1  0  0  0  0
 22 52  1  1  0  0  0
 15 14  1  0  0  0  0
  5  6  1  0  0  0  0
 15 42  1  6  0  0  0
 17 44  1  0  0  0  0
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  9 32  1  0  0  0  0
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  7 31  1  0  0  0  0
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  5 28  1  0  0  0  0
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  1 25  1  0  0  0  0
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  1 27  1  0  0  0  0
 16 43  1  0  0  0  0
 21 51  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
  6 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=O)[C@@]1(C([H])=C2C([H])([H])C([H])([H])[C@]3([H])[C@](C([H])([H])[H])(C([H])([H])O[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]2([H])C([H])([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-16,21-23H,4-7,9-12H2,1-3H3/t14-,15-,16-,18+,19+,20+/m1/s1

> <INCHI_KEY>
LODMADPUDAMZJC-LFMXGZDGSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.10397741966489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl]-2-hydroxyethan-1-one

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
1.7714916933333331

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.888150129318063

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.807131950777567

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7022592252013062

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
94.38719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]-2-hydroxyethanone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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    1.0074   -1.8052    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229   -3.0424    1.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -3.9765    2.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    1.3679   -0.7472 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1683    2.2201   -1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    3.1661   -2.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    3.9287   -3.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    4.1621   -4.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1911    1.1010   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5960   -1.1371   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -0.3932   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.7757   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755    1.3732    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9099   -1.4163    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -0.7837    3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -0.2684    3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533   -1.8537    3.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.3732    3.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -2.3339    2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -0.8335    3.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2651   -3.0337    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -3.4487    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -4.2739    2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994    2.0236    0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692    1.5986   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766    2.8131   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430    3.8694   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328    3.7775   -3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  1
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 11 10  1  0
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 10  9  1  0
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 24  2  1  0
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 22  8  1  0
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 12 11  1  0
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  2  7  1  0
  2  1  1  0
 22 23  1  0
 15 16  1  0
  8  7  2  0
 20 21  1  0
 24 23  1  0
 12 13  1  6
 15 17  1  0
 22 52  1  1
 15 14  1  0
  5  6  1  0
 15 42  1  6
 17 44  1  0
 17 45  1  0
 14 40  1  0
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 23 53  1  0
 23 54  1  0
 19 46  1  0
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  5 28  1  0
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  1 25  1  0
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 16 43  1  0
 21 51  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
  6 30  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       1.262   3.405  -4.326  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.397   2.398  -3.550  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.431   1.600  -4.588  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.093   0.484  -5.003  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.687   2.251  -5.166  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.160   1.542  -6.305  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.299   1.434  -2.804  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.082   1.000  -1.548  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.106   0.150  -0.835  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.504  -1.028  -0.067  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.322  -0.577   0.817  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.805   0.087  -0.069  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.355  -0.856  -1.172  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.979   0.517   0.842  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.477  -0.597   1.760  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.522  -0.061   2.570  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.356  -1.098   2.663  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.127  -1.640   1.889  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.007  -1.805   2.941  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.423  -3.042   1.302  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.778  -3.977   2.320  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.160   1.368  -0.747  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.168   2.220  -1.554  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.477   3.166  -2.535  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.961   3.929  -3.663  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.646   4.162  -4.822  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.852   2.908  -5.106  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.478   2.247  -4.413  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.469   3.274  -5.478  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.764   0.648  -6.250  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.191   1.101  -3.335  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.640   0.795  -0.124  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.861  -0.233  -1.532  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.192  -1.809  -0.770  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.300  -1.468   0.543  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.716   0.254   1.427  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.596  -1.137  -1.907  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.177  -0.393  -1.727  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.777  -1.776  -0.774  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.676   1.373   1.461  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.824   0.885   0.245  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.910  -1.416   1.178  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.846  -0.784   3.136  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.045  -0.268   3.315  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.753  -1.854   3.352  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.667  -2.373   3.815  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.872  -2.334   2.527  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.354  -0.834   3.311  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.265  -3.034   0.616  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.439  -3.449   0.763  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.044  -4.274   2.747  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.199   2.024   0.061  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.869   1.599  -2.116  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.777   2.813  -0.860  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.143   3.869  -1.961  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.233   3.777  -3.041  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2   24    3    7    1                                             
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6   28   29                                             
CONECT    6    5   30                                                       
CONECT    7    2    8   31                                                  
CONECT    8    9   22    7                                                  
CONECT    9   10    8   32   33                                             
CONECT   10   11    9   34   35                                             
CONECT   11   10   36   18   12                                             
CONECT   12   22   14   11   13                                             
CONECT   13   12   37   38   39                                             
CONECT   14   12   15   40   41                                             
CONECT   15   16   17   14   42                                             
CONECT   16   15   43                                                       
CONECT   17   18   15   44   45                                             
CONECT   18   17   19   20   11                                             
CONECT   19   18   46   47   48                                             
CONECT   20   18   21   49   50                                             
CONECT   21   20   51                                                       
CONECT   22   12    8   23   52                                             
CONECT   23   22   24   53   54                                             
CONECT   24    2   23   55   56                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
    1.2622    3.4045   -4.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    2.3983   -3.5497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4309    1.5997   -4.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6865    2.2506   -5.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0824    1.0000   -1.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0074   -1.8052    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1683    2.2201   -1.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    3.1661   -2.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    3.9287   -3.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    4.1621   -4.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.9077   -5.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775    2.2466   -4.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4692    3.2743   -5.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637    0.6480   -6.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1911    1.1010   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398    0.7947   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615   -0.2329   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -1.8086   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -1.4677    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156    0.2542    1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -1.1371   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -0.3932   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.7757   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755    1.3732    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8236    0.8851    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099   -1.4163    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -0.7837    3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0453   -0.2684    3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533   -1.8537    3.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.3732    3.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -2.3339    2.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -0.8335    3.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2651   -3.0337    0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4386   -3.4487    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -4.2739    2.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994    2.0236    0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692    1.5986   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766    2.8131   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430    3.8694   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328    3.7775   -3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  1
 12 22  1  0
 11 10  1  0
 18 20  1  0
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 11 36  1  1
 24  2  1  0
  9  8  1  0
 22  8  1  0
 18 11  1  0
 12 14  1  0
  2  3  1  6
  3  5  1  0
 12 11  1  0
  3  4  2  0
  2  7  1  0
  2  1  1  0
 22 23  1  0
 15 16  1  0
  8  7  2  0
 20 21  1  0
 24 23  1  0
 12 13  1  6
 15 17  1  0
 22 52  1  1
 15 14  1  0
  5  6  1  0
 15 42  1  6
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 14 40  1  0
 14 41  1  0
 10 34  1  0
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  9 32  1  0
  9 33  1  0
 23 53  1  0
 23 54  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
  7 31  1  0
 24 55  1  0
 24 56  1  0
  5 28  1  0
  5 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 16 43  1  0
 21 51  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
  6 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl]-2-hydroxyethan-1-one

Traditional Name

1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]-2-hydroxyethanone

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(=O)[C@@]1(C([H])=C2C([H])([H])C([H])([H])[C@]3([H])[C@](C([H])([H])[H])(C([H])([H])O[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]2([H])C([H])([H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H32O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-16,21-23H,4-7,9-12H2,1-3H3/t14-,15-,16-,18+,19+,20+/m1/s1

InChI Key

LODMADPUDAMZJC-LFMXGZDGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sigesbeckia orientalis	JEOL database	Xiang, Y., et al, J. Nat. Prod. 67, 1517 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Pimarane diterpenoid
18-oxosteroid
Oxosteroid
Hydrophenanthrene
Phenanthrene
Alpha-hydroxy ketone
Cyclic alcohol
Ketone
Secondary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Primary 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	1.86	ALOGPS
logP	1.77	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.39 m³·mol⁻¹	ChemAxon
Polarizability	38.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

9647992

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11473162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiang, Y., et al. (2004). Xiang, Y., et al, J. Nat. Prod. 67, 1517 (2004). J. Nat. Prod..

Showing NP-Card for Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene (NP0027481)

MOL for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

3D MOL for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

3D SDF for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

3D-SDF for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

PDB for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

3D PDB for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

SMILES for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

INCHI for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

Structure for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)

3D Structure for NP0027481 (Ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene)