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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:43:54 UTC

Update Date

2021-09-26 23:18:08 UTC

HMDB ID

HMDB0260179

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one

Description

5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3-dien-14-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Based on a literature review very few articles have been published on 5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3-dien-14-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (8r,9s,13s,14s)-3-hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3h-cyclopenta[a]phenanthren-17-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0260179
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyc...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.8114   -1.4101    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.5771   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -1.3867   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -1.2280   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.8287    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.5805   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    0.5297    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    1.3437    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    1.5171    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    0.2622    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    0.6687   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5335    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    1.3052   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186   -0.0197   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5923   -0.5268   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263    0.9004   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4670   -0.2583   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780   -0.0397   -1.1864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8007   -1.4932   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.6321   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -1.8286    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8452   -0.8112    1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1315   -2.4439   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -1.0639   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2785    2.0687    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -0.0761    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    1.0851   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    2.5937    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240    1.2237    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975    1.3892    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    2.1121   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    1.2605   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9598    1.7816    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154   -0.3521    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592    0.5926   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -2.3480   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -2.5909   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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M  END


  Mrv1652309122101442D          

 20 23  0  0  0  0            999 V2000
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
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 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0260179

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,12,14-16,19H,2,4,6-10H2,1H3

> <INCHI_KEY>
PPVLHOVXXOMTJL-UHFFFAOYSA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.388

> <EXACT_MASS>
272.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.635453021859377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.811985914000001

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957539207973408

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.43565010494848

> <JCHEM_PKA_STRONGEST_BASIC>
-1.733445857813296

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
80.8798

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0260179
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyc...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.8114   -1.4101    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.5771   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -1.3867   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -1.2280   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.8287    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.5805   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    0.5297    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    1.3437    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    1.5171    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    0.2622    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    0.6687   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5335    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    1.3052   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186   -0.0197   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5923   -0.5268   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263    0.9004   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4670   -0.2583   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780   -0.0397   -1.1864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8007   -1.4932   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.6321   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -1.8286    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8452   -0.8112    1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -2.3023    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1315   -2.4439   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -1.0639   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.5002   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1139   -2.2104   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390   -1.7524    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616    0.8136    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    2.3385    1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1460    2.1616    0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785    2.0687    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -0.0761    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    1.0851   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    2.5937    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240    1.2237    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975    1.3892    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    2.1121   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    1.2605   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9598    1.7816    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154   -0.3521    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592    0.5926   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -2.3480   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -2.5909   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
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  9 10  1  0
 10 11  1  0
 11 12  1  0
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 13 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  2  1  0
 14  2  1  0
 10  5  1  0
 20  6  1  0
  1 21  1  0
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 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.882  -1.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0260179
HETATM    1  C1  UNL     1      -2.811  -1.410   0.942  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.553  -0.577  -0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.815  -1.387  -1.290  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.327  -1.228  -1.222  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.206  -0.829   0.116  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.656  -0.581  -0.024  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.273   0.530   0.325  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.674   1.344   1.390  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.227   1.517   1.065  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.535   0.262   0.796  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.748   0.669  -0.013  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.717   1.534   0.716  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.000   1.305  -0.093  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.819  -0.020  -0.740  1.00  0.00           C  
HETATM   15  O1  UNL     1      -4.592  -0.527  -1.516  1.00  0.00           O  
HETATM   16  C15 UNL     1       3.526   0.900  -0.377  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.467  -0.258  -0.335  1.00  0.00           C  
HETATM   18  O2  UNL     1       5.578  -0.040  -1.186  1.00  0.00           O  
HETATM   19  C17 UNL     1       3.801  -1.493  -0.734  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.497  -1.632  -0.584  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.857  -1.829   0.836  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.845  -0.811   1.895  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.172  -2.302   1.043  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.131  -2.444  -1.170  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.174  -1.064  -2.290  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.025  -0.500  -1.985  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.114  -2.210  -1.501  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.139  -1.752   0.766  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.762   0.814   2.359  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.128   2.339   1.474  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.146   2.162   0.143  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.278   2.069   1.912  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.949  -0.076   1.794  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.466   1.085  -1.001  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.402   2.594   0.669  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.824   1.224   1.755  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.897   1.389   0.514  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.983   2.112  -0.881  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.328   1.260  -1.414  1.00  0.00           H  
HETATM   40  H20 UNL     1       3.960   1.782   0.153  1.00  0.00           H  
HETATM   41  H21 UNL     1       4.815  -0.352   0.716  1.00  0.00           H  
HETATM   42  H22 UNL     1       6.159   0.593  -0.681  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.346  -2.348  -1.169  1.00  0.00           H  
HETATM   44  H24 UNL     1       2.071  -2.591  -0.905  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   11   14
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   10   28
CONECT    6    7    7   20
CONECT    7    8   16
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   33
CONECT   11   12   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   15   15
CONECT   16   17   39   40
CONECT   17   18   19   41
CONECT   18   42
CONECT   19   20   20   43
CONECT   20   44
END

HMDB0260179
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyc...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.8114   -1.4101    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -0.5771   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -1.3867   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -1.2280   -1.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.8287    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556   -0.5805   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    0.5297    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    1.3437    1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267    1.5171    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    0.2622    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    0.6687   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    1.5335    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    1.3052   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186   -0.0197   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5923   -0.5268   -1.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5263    0.9004   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4670   -0.2583   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780   -0.0397   -1.1864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8007   -1.4932   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.6321   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567   -1.8286    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8452   -0.8112    1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -2.3023    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1315   -2.4439   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -1.0639   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.5002   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1139   -2.2104   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390   -1.7524    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616    0.8136    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    2.3385    1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1460    2.1616    0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2785    2.0687    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -0.0761    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    1.0851   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    2.5937    0.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240    1.2237    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8975    1.3892    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    2.1121   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    1.2605   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9598    1.7816    0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154   -0.3521    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592    0.5926   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -2.3480   -1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -2.5909   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  2  1  0
 14  2  1  0
 10  5  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄O₂

Average Molecular Weight

272.388

Monoisotopic Molecular Weight

272.177630013

IUPAC Name

5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one

Traditional Name

5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O

InChI Identifier

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,12,14-16,19H,2,4,6-10H2,1H3

InChI Key

PPVLHOVXXOMTJL-UHFFFAOYSA-N

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

Oxosteroid
17-oxosteroid
Hydroxysteroid
3-hydroxysteroid
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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.1	ALOGPS
logP	2.81	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.44	ChemAxon
pKa (Strongest Basic)	-1.7	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	80.88 m³·mol⁻¹	ChemAxon
Polarizability	31.64 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	169.552	32859911
AllCCS	[M+H-H2O]+	166.198	32859911
AllCCS	[M+Na]+	173.556	32859911
AllCCS	[M+NH4]+	172.662	32859911
AllCCS	[M-H]-	174.266	32859911
AllCCS	[M+Na-2H]-	174.129	32859911
AllCCS	[M+HCOO]-	174.109	32859911
DeepCCS	[M-2H]-	198.573	30932474
DeepCCS	[M+Na]+	174.101	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one	CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O	3275.6	Standard polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one	CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O	2446.4	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one	CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O	2556.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C4	2635.1	Semi standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C4	2531.2	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C4	3004.1	Standard polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C4	3135.4	Semi standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C4	2921.1	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C4	3264.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ox-0590000000-d754fc3aec6e8e2ffb0b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

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DrugBank ID

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Phenol Explorer Compound ID

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FooDB ID

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KNApSAcK ID

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Chemspider ID

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KEGG Compound ID

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BioCyc ID

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BiGG ID

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METLIN ID

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PDB ID

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ChEBI ID

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Food Biomarker Ontology

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VMH ID

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Good Scents ID

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References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one (HMDB0260179)

MOL for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

3D MOL for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

3D SDF for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

3D-SDF for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

PDB for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

3D PDB for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

SMILES for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

INCHI for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

Structure for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

3D Structure for HMDB0260179 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra