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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:43:49 UTC

Update Date

2021-09-26 23:18:08 UTC

HMDB ID

HMDB0260178

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

Description

(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Based on a literature review very few articles have been published on (8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (8r,9s,13s,14s)-3-hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6h-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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-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


  Mrv1652309122101442D          

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M  END

HMDB0260178
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-oc...
 93 96  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309122101442D          

 39 42  0  0  0  0            999 V2000
   -5.9410   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0260178

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O)=CC2=C1C1CCC3(C)C(CCC3=O)C1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C36H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-33(38)31-26-28(37)25-27-19-20-29-30(35(27)31)23-24-36(2)32(29)21-22-34(36)39/h10-11,25-26,29-30,32,37H,3-9,12-24H2,1-2H3

> <INCHI_KEY>
JWLQYWPSIIMIFS-UHFFFAOYSA-N

> <FORMULA>
C36H54O3

> <MOLECULAR_WEIGHT>
534.825

> <EXACT_MASS>
534.407295599

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
68.36038104413876

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-15-methyl-3-(octadec-9-enoyl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
8.96

> <JCHEM_LOGP>
10.873820718

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.326680441101722

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.319909229899645

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9598082341962675

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
164.24370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-15-methyl-3-(octadec-9-enoyl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0260178
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-oc...
 93 96  0  0  0  0  0  0  0  0999 V2000
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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     -11.090  -1.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.586  -3.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.073  -3.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.569  -4.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.057  -5.166   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.553  -6.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.041  -6.912   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.537  -8.367   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.024  -8.658   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.520 -10.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.008 -10.404   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.512  -9.531   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.520  -8.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.033  -8.658   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.041  -7.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.553  -7.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.057  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.569  -9.531   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.049 -10.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.537 -10.113   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.529 -11.277   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.033 -12.732   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.545 -13.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.553 -11.859   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.065 -12.150   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.073 -10.986   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.586 -11.277   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.090 -12.732   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.082 -13.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.569 -13.605   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.561 -14.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.049 -14.479   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.877 -15.215   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.377 -14.866   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.509 -13.331   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.827 -12.536   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.214 -11.680   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.016 -10.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   39                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36   38                                             
CONECT   30   29   31   34                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   24                                                       
CONECT   34   30   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   29   37                                                  
CONECT   37   36                                                            
CONECT   38   29                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0260178
HETATM    1  C1  UNL     1       8.370   3.622  -0.985  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.039   2.854   0.128  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.011   1.357  -0.192  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.595   0.887  -0.332  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.553  -0.573  -0.670  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.213  -1.367   0.425  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.171  -2.851   0.177  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.726  -3.315   0.162  1.00  0.00           C  
HETATM    9  C9  UNL     1       6.054  -3.056   1.441  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.999  -2.372   1.655  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.191  -1.674   0.649  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.737  -2.166   0.667  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.022  -1.380  -0.411  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.069   0.099  -0.185  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.445   0.560   1.092  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.002   0.253   1.207  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.857   0.882   0.141  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.265   0.502   0.426  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.679   1.021   1.476  1.00  0.00           O  
HETATM   20  C19 UNL     1      -2.983  -0.378  -0.488  1.00  0.00           C  
HETATM   21  C20 UNL     1      -2.237  -1.167  -1.379  1.00  0.00           C  
HETATM   22  C21 UNL     1      -2.792  -2.051  -2.261  1.00  0.00           C  
HETATM   23  O2  UNL     1      -1.982  -2.792  -3.108  1.00  0.00           O  
HETATM   24  C22 UNL     1      -4.160  -2.186  -2.287  1.00  0.00           C  
HETATM   25  C23 UNL     1      -4.901  -1.419  -1.419  1.00  0.00           C  
HETATM   26  C24 UNL     1      -4.347  -0.529  -0.533  1.00  0.00           C  
HETATM   27  C25 UNL     1      -5.195   0.316   0.359  1.00  0.00           C  
HETATM   28  C26 UNL     1      -5.053   1.761   0.024  1.00  0.00           C  
HETATM   29  C27 UNL     1      -6.164   2.177  -0.941  1.00  0.00           C  
HETATM   30  C28 UNL     1      -7.392   2.195  -0.060  1.00  0.00           C  
HETATM   31  C29 UNL     1      -7.244   3.203   1.065  1.00  0.00           C  
HETATM   32  C30 UNL     1      -8.548   2.612  -0.885  1.00  0.00           C  
HETATM   33  O3  UNL     1      -8.580   3.472  -1.725  1.00  0.00           O  
HETATM   34  C31 UNL     1      -9.680   1.726  -0.447  1.00  0.00           C  
HETATM   35  C32 UNL     1      -8.902   0.406  -0.312  1.00  0.00           C  
HETATM   36  C33 UNL     1      -7.708   0.841   0.480  1.00  0.00           C  
HETATM   37  C34 UNL     1      -6.582  -0.132   0.570  1.00  0.00           C  
HETATM   38  C35 UNL     1      -6.994  -1.402  -0.126  1.00  0.00           C  
HETATM   39  C36 UNL     1      -6.379  -1.604  -1.470  1.00  0.00           C  
HETATM   40  H1  UNL     1       8.275   2.963  -1.890  1.00  0.00           H  
HETATM   41  H2  UNL     1       8.974   4.504  -1.284  1.00  0.00           H  
HETATM   42  H3  UNL     1       7.332   3.925  -0.724  1.00  0.00           H  
HETATM   43  H4  UNL     1       8.419   3.003   1.050  1.00  0.00           H  
HETATM   44  H5  UNL     1      10.083   3.155   0.281  1.00  0.00           H  
HETATM   45  H6  UNL     1       9.493   0.839   0.674  1.00  0.00           H  
HETATM   46  H7  UNL     1       9.540   1.201  -1.143  1.00  0.00           H  
HETATM   47  H8  UNL     1       7.079   1.516  -1.088  1.00  0.00           H  
HETATM   48  H9  UNL     1       7.061   1.051   0.649  1.00  0.00           H  
HETATM   49  H10 UNL     1       6.534  -0.895  -0.867  1.00  0.00           H  
HETATM   50  H11 UNL     1       8.127  -0.769  -1.634  1.00  0.00           H  
HETATM   51  H12 UNL     1       9.289  -1.112   0.538  1.00  0.00           H  
HETATM   52  H13 UNL     1       7.649  -1.118   1.371  1.00  0.00           H  
HETATM   53  H14 UNL     1       8.744  -3.420   0.912  1.00  0.00           H  
HETATM   54  H15 UNL     1       8.543  -3.008  -0.869  1.00  0.00           H  
HETATM   55  H16 UNL     1       6.696  -4.435   0.014  1.00  0.00           H  
HETATM   56  H17 UNL     1       6.170  -2.896  -0.689  1.00  0.00           H  
HETATM   57  H18 UNL     1       6.552  -3.532   2.322  1.00  0.00           H  
HETATM   58  H19 UNL     1       4.632  -2.278   2.702  1.00  0.00           H  
HETATM   59  H20 UNL     1       4.536  -1.887  -0.372  1.00  0.00           H  
HETATM   60  H21 UNL     1       4.242  -0.588   0.897  1.00  0.00           H  
HETATM   61  H22 UNL     1       2.285  -2.072   1.659  1.00  0.00           H  
HETATM   62  H23 UNL     1       2.768  -3.225   0.341  1.00  0.00           H  
HETATM   63  H24 UNL     1       1.014  -1.749  -0.608  1.00  0.00           H  
HETATM   64  H25 UNL     1       2.605  -1.573  -1.359  1.00  0.00           H  
HETATM   65  H26 UNL     1       1.468   0.549  -1.031  1.00  0.00           H  
HETATM   66  H27 UNL     1       3.087   0.514  -0.346  1.00  0.00           H  
HETATM   67  H28 UNL     1       1.694   1.625   1.278  1.00  0.00           H  
HETATM   68  H29 UNL     1       1.958  -0.022   1.916  1.00  0.00           H  
HETATM   69  H30 UNL     1      -0.346   0.631   2.211  1.00  0.00           H  
HETATM   70  H31 UNL     1      -0.152  -0.834   1.227  1.00  0.00           H  
HETATM   71  H32 UNL     1      -0.745   2.006   0.328  1.00  0.00           H  
HETATM   72  H33 UNL     1      -0.528   0.756  -0.880  1.00  0.00           H  
HETATM   73  H34 UNL     1      -1.138  -1.048  -1.338  1.00  0.00           H  
HETATM   74  H35 UNL     1      -2.369  -3.456  -3.773  1.00  0.00           H  
HETATM   75  H36 UNL     1      -4.646  -2.888  -2.984  1.00  0.00           H  
HETATM   76  H37 UNL     1      -4.677   0.196   1.370  1.00  0.00           H  
HETATM   77  H38 UNL     1      -4.124   2.025  -0.524  1.00  0.00           H  
HETATM   78  H39 UNL     1      -5.068   2.353   0.950  1.00  0.00           H  
HETATM   79  H40 UNL     1      -6.012   3.202  -1.318  1.00  0.00           H  
HETATM   80  H41 UNL     1      -6.284   1.416  -1.707  1.00  0.00           H  
HETATM   81  H42 UNL     1      -8.192   3.695   1.314  1.00  0.00           H  
HETATM   82  H43 UNL     1      -6.476   3.957   0.874  1.00  0.00           H  
HETATM   83  H44 UNL     1      -6.970   2.612   1.989  1.00  0.00           H  
HETATM   84  H45 UNL     1     -10.027   2.063   0.536  1.00  0.00           H  
HETATM   85  H46 UNL     1     -10.472   1.666  -1.194  1.00  0.00           H  
HETATM   86  H47 UNL     1      -8.716   0.092  -1.333  1.00  0.00           H  
HETATM   87  H48 UNL     1      -9.588  -0.231   0.285  1.00  0.00           H  
HETATM   88  H49 UNL     1      -8.130   1.022   1.510  1.00  0.00           H  
HETATM   89  H50 UNL     1      -6.628  -0.467   1.680  1.00  0.00           H  
HETATM   90  H51 UNL     1      -8.084  -1.437  -0.205  1.00  0.00           H  
HETATM   91  H52 UNL     1      -6.725  -2.300   0.510  1.00  0.00           H  
HETATM   92  H53 UNL     1      -6.557  -2.659  -1.760  1.00  0.00           H  
HETATM   93  H54 UNL     1      -6.764  -0.973  -2.282  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   49   50
CONECT    6    7   51   52
CONECT    7    8   53   54
CONECT    8    9   55   56
CONECT    9   10   10   57
CONECT   10   11   58
CONECT   11   12   59   60
CONECT   12   13   61   62
CONECT   13   14   63   64
CONECT   14   15   65   66
CONECT   15   16   67   68
CONECT   16   17   69   70
CONECT   17   18   71   72
CONECT   18   19   19   20
CONECT   20   21   21   26
CONECT   21   22   73
CONECT   22   23   24   24
CONECT   23   74
CONECT   24   25   75
CONECT   25   26   26   39
CONECT   26   27
CONECT   27   28   37   76
CONECT   28   29   77   78
CONECT   29   30   79   80
CONECT   30   31   32   36
CONECT   31   81   82   83
CONECT   32   33   33   34
CONECT   34   35   84   85
CONECT   35   36   86   87
CONECT   36   37   88
CONECT   37   38   89
CONECT   38   39   90   91
CONECT   39   92   93
END

HMDB0260178
     RDKit          3D
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-oc...
 93 96  0  0  0  0  0  0  0  0999 V2000
    8.3703    3.6220   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0387    2.8541    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0112    1.3565   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5954    0.8872   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5531   -0.5728   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2129   -1.3666    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1712   -2.8508    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7257   -3.3147    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0539   -3.0563    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9991   -2.3719    1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914   -1.6739    0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -2.1664    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217   -1.3800   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.0989   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450    0.5601    1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0021    0.2526    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    0.8824    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650    0.5021    0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790    1.0209    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -0.3775   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -1.1665   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7918   -2.0510   -2.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9824   -2.7917   -3.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1605   -2.1859   -2.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9008   -1.4186   -1.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3466   -0.5290   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1953    0.3163    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0531    1.7610    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1635    2.1767   -0.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3924    2.1949   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2435    3.2028    1.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5480    2.6120   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5795    3.4717   -1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6804    1.7263   -0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9024    0.4056   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7079    0.8409    0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5818   -0.1317    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9940   -1.4018   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3793   -1.6040   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750    2.9633   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9739    4.5041   -1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3320    3.9249   -0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4187    3.0028    1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0830    3.1546    0.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4932    0.8388    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5399    1.2011   -1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0785    1.5156   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0611    1.0514    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5344   -0.8950   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1270   -0.7685   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893   -1.1117    0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6494   -1.1179    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7439   -3.4197    0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5426   -3.0077   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6958   -4.4349    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1699   -2.8960   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5519   -3.5320    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318   -2.2783    2.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -1.8867   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420   -0.5880    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2852   -2.0720    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682   -3.2251    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142   -1.7488   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050   -1.5733   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    0.5490   -1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874    0.5137   -0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937    1.6252    1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -0.0220    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    0.6313    2.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525   -0.8339    1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450    2.0060    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5280    0.7556   -0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -1.0482   -1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -3.4556   -3.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457   -2.8881   -2.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6769    0.1955    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237    2.0246   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.3532    0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0119    3.2025   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2838    1.4157   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1924    3.6952    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4764    3.9572    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9704    2.6124    1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0275    2.0632    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4717    1.6659   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7164    0.0921   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5878   -0.2312    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1297    1.0221    1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6279   -0.4666    1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0840   -1.4368   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7246   -2.3004    0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5565   -2.6593   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7644   -0.9731   -2.2821 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
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  8  9  1  0
  9 10  2  3
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 39 93  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₆H₅₄O₃

Average Molecular Weight

534.825

Monoisotopic Molecular Weight

534.407295599

IUPAC Name

5-hydroxy-15-methyl-3-(octadec-9-enoyl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

Traditional Name

5-hydroxy-15-methyl-3-(octadec-9-enoyl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O)=CC2=C1C1CCC3(C)C(CCC3=O)C1CC2

InChI Identifier

InChI=1S/C36H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-33(38)31-26-28(37)25-27-19-20-29-30(35(27)31)23-24-36(2)32(29)21-22-34(36)39/h10-11,25-26,29-30,32,37H,3-9,12-24H2,1-2H3

InChI Key

JWLQYWPSIIMIFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
Oxosteroid
17-oxosteroid
Hydroxysteroid
3-hydroxysteroid
Phenanthrene
Butyrophenone
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	8.96	ALOGPS
logP	10.87	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	164.24 m³·mol⁻¹	ChemAxon
Polarizability	68.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	237.982	32859911
AllCCS	[M+H-H2O]+	236.727	32859911
AllCCS	[M+Na]+	239.441	32859911
AllCCS	[M+NH4]+	239.119	32859911
AllCCS	[M-H]-	230.254	32859911
AllCCS	[M+Na-2H]-	234.752	32859911
AllCCS	[M+HCOO]-	239.827	32859911
DeepCCS	[M+H]+	231.69	30932474
DeepCCS	[M-H]-	229.332	30932474
DeepCCS	[M-2H]-	262.215	30932474
DeepCCS	[M+Na]+	238.719	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.53 minutes	32390414
Predicted by Siyang on May 30, 2022	32.6174 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4345.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	832.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	369.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	363.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	918.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1549.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1163.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3062.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	914.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2705.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1049.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	709.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	486.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	658.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O)=CC2=C1C1CCC3(C)C(CCC3=O)C1CC2	3812.5	Standard polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O)=CC2=C1C1CCC3(C)C(CCC3=O)C1CC2	4615.7	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O)=CC2=C1C1CCC3(C)C(CCC3=O)C1CC2	4449.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C)=CCC3C1CC2	4252.9	Semi standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C)=CCC3C1CC2	4052.3	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C)=CCC3C1CC2	4535.3	Standard polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C(C)(C)C)=CCC3C1CC2	4693.8	Semi standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C(C)(C)C)=CCC3C1CC2	4329.8	Standard non polar	33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1CCC3(C)C(O[Si](C)(C)C(C)(C)C)=CCC3C1CC2	4664.0	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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-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

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73719245

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one (HMDB0260178)

MOL for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

3D MOL for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

3D SDF for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

3D-SDF for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

PDB for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

3D PDB for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

SMILES for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

INCHI for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

Structure for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

3D Structure for HMDB0260178 ((8R,9S,13S,14S)-3-Hydroxy-13-methyl-1-octadec-9-enoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra