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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-29 06:03:27 UTC

Update Date

2021-09-26 22:48:55 UTC

HMDB ID

HMDB0242295

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol

Description

(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol, also known as 17 alpha-ethinylestriol 3-cyclopentyl ether or EE3CPE, belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. Based on a literature review very few articles have been published on (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (16r,17r)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-16,17-diol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 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

  Mrv1652308292108132D          

 28 32  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
    5.5484   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927    0.9312    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
   -1.1901    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826    1.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    2.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    2.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271    2.1617    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
M  END

HMDB0242295
     RDKit          3D
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydr...
 60 64  0  0  0  0  0  0  0  0999 V2000
   -4.9806    0.5289    3.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0591    0.1628    2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1520   -0.2959    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118   -1.2506    0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248    0.9329   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1695    1.8664    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9099    1.4818   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    0.5403    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216    0.5027   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155    0.9840   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.1554   -1.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.2178   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843    0.3874   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921   -0.4043    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653   -0.2928    0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984    0.6215   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2886    1.3721    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5844    0.6240    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4989   -0.5285   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4318   -0.0534   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -1.4132    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -1.5800    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.7776    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -0.9202    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.6323    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -1.7989    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -0.7743    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.1721   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8936    0.8468    4.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8396   -0.9661   -0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523    0.5460   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264    2.3346   -0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    2.4739    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.6113   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    0.7964    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    1.1017    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    1.9922   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596    0.2531   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    2.1895   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    1.0131   -2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    1.1792   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322    1.3091   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4338    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4768    2.3746    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4617    1.2479    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109    0.2516    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1502   -1.4551    0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4567   -0.6764   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0296   -0.9218   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654    0.6412   -1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789   -2.0642    1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575   -2.3743    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -1.4192   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217   -1.0706    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -2.6398    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -2.8370    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662   -1.7448    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -0.3624   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -2.1318   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825   -1.4168   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27  3  1  0
 27  8  1  0
 24  9  1  0
 23 12  1  0
 20 16  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

  Mrv1652308292108132D          

 28 32  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
    5.5484   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927    0.9312    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
   -1.1901    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826    1.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    2.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    2.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271    2.1617    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242295

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=C3C=CC(OC3CCCC3)=C4)C1CC(O)C2(O)C#C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O3/c1-3-25(27)23(26)15-22-21-10-8-16-14-18(28-17-6-4-5-7-17)9-11-19(16)20(21)12-13-24(22,25)2/h1,9,11,14,17,20-23,26-27H,4-8,10,12-13,15H2,2H3

> <INCHI_KEY>
CHZJRGNDJLJLAW-UHFFFAOYSA-N

> <FORMULA>
C25H32O3

> <MOLECULAR_WEIGHT>
380.528

> <EXACT_MASS>
380.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.93611455549419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-13,14-diol

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
4.323045403666668

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.477498357609665

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.0126546926785

> <JCHEM_PKA_STRONGEST_BASIC>
-3.39224443766924

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
109.63149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-13,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242295
     RDKit          3D
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydr...
 60 64  0  0  0  0  0  0  0  0999 V2000
   -4.9806    0.5289    3.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0591    0.1628    2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1520   -0.2959    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118   -1.2506    0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248    0.9329   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1695    1.8664    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9099    1.4818   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    0.5403    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216    0.5027   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155    0.9840   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.1554   -1.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.2178   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843    0.3874   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921   -0.4043    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653   -0.2928    0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984    0.6215   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2886    1.3721    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5844    0.6240    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4989   -0.5285   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4318   -0.0534   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -1.4132    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -1.5800    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.7776    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -0.9202    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.6323    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -1.7989    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -0.7743    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.1721   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8936    0.8468    4.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8396   -0.9661   -0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523    0.5460   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264    2.3346   -0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    2.4739    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.6113   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    0.7964    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    1.1017    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    1.9922   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596    0.2531   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    2.1895   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    1.0131   -2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    1.1792   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322    1.3091   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4338    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4768    2.3746    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4617    1.2479    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109    0.2516    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1502   -1.4551    0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4567   -0.6764   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0296   -0.9218   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654    0.6412   -1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789   -2.0642    1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575   -2.3743    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -1.4192   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217   -1.0706    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -2.6398    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -2.8370    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662   -1.7448    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -0.3624   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -2.1318   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825   -1.4168   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27  3  1  0
 27  8  1  0
 24  9  1  0
 23 12  1  0
 20 16  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

HEADER    PROTEIN                                 29-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-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  C   UNK     0      10.357  -0.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.777  -1.455   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.163  -1.787   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.813   1.738   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.701   3.189   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.751   4.728   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.302   5.251   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.357   4.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    2   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    9                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0242745
HETATM    1  C1  UNL     1      -6.955   0.754   1.577  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.136   0.129   0.941  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.133  -0.626   0.178  1.00  0.00           C  
HETATM    4  O1  UNL     1      -5.437  -1.971   0.244  1.00  0.00           O  
HETATM    5  C4  UNL     1      -5.163  -0.180  -1.249  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.639  -1.133  -2.129  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.691   0.138  -1.553  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.269   0.735  -0.245  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.801   0.931  -0.083  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.231   2.010  -0.941  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.087   2.420  -0.268  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.957   1.184  -0.230  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.317   1.302  -0.166  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.178   0.189  -0.131  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.527   0.464  -0.066  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.517  -0.506  -0.025  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.385  -0.314   1.226  1.00  0.00           C  
HETATM   18  C15 UNL     1       7.784  -0.553   0.720  1.00  0.00           C  
HETATM   19  C16 UNL     1       7.749   0.227  -0.598  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.467  -0.309  -1.196  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.618  -1.068  -0.165  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.236  -1.171  -0.230  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.403  -0.072  -0.263  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.056  -0.348  -0.333  1.00  0.00           C  
HETATM   25  C22 UNL     1      -1.450  -1.284   0.817  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.941  -1.528   0.780  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.772  -0.293   0.741  1.00  0.00           C  
HETATM   28  C25 UNL     1      -3.930   0.312   2.125  1.00  0.00           C  
HETATM   29  H1  UNL     1      -7.682   1.298   2.149  1.00  0.00           H  
HETATM   30  H2  UNL     1      -5.679  -2.196   1.176  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.693   0.804  -1.367  1.00  0.00           H  
HETATM   32  H4  UNL     1      -6.133  -0.760  -2.895  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.611   0.846  -2.403  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.229  -0.848  -1.770  1.00  0.00           H  
HETATM   35  H7  UNL     1      -3.850   1.651  -0.086  1.00  0.00           H  
HETATM   36  H8  UNL     1      -1.639   1.163   1.013  1.00  0.00           H  
HETATM   37  H9  UNL     1      -1.876   2.892  -1.020  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.960   1.580  -1.931  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.544   3.211  -0.884  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.096   2.770   0.762  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.736   2.311  -0.140  1.00  0.00           H  
HETATM   42  H14 UNL     1       5.151  -1.545  -0.048  1.00  0.00           H  
HETATM   43  H15 UNL     1       6.114  -1.062   2.002  1.00  0.00           H  
HETATM   44  H16 UNL     1       6.325   0.724   1.574  1.00  0.00           H  
HETATM   45  H17 UNL     1       8.564  -0.181   1.384  1.00  0.00           H  
HETATM   46  H18 UNL     1       7.871  -1.647   0.492  1.00  0.00           H  
HETATM   47  H19 UNL     1       8.620   0.018  -1.228  1.00  0.00           H  
HETATM   48  H20 UNL     1       7.617   1.296  -0.338  1.00  0.00           H  
HETATM   49  H21 UNL     1       6.632  -1.249  -1.720  1.00  0.00           H  
HETATM   50  H22 UNL     1       6.057   0.414  -1.935  1.00  0.00           H  
HETATM   51  H23 UNL     1       3.243  -1.941  -0.140  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.869  -2.203  -0.256  1.00  0.00           H  
HETATM   53  H25 UNL     1      -1.245  -0.801  -1.315  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.110  -0.836   1.753  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.953  -2.246   0.612  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.192  -2.100   1.700  1.00  0.00           H  
HETATM   57  H29 UNL     1      -3.151  -2.204  -0.076  1.00  0.00           H  
HETATM   58  H30 UNL     1      -3.959   1.421   2.078  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.043   0.070   2.775  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.862  -0.086   2.586  1.00  0.00           H  
CONECT    1    2    2    2   29
CONECT    2    3
CONECT    3    4    5   27
CONECT    4   30
CONECT    5    6    7   31
CONECT    6   32
CONECT    7    8   33   34
CONECT    8    9   27   35
CONECT    9   10   24   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   13   23
CONECT   13   14   41
CONECT   14   15   21   21
CONECT   15   16
CONECT   16   17   20   42
CONECT   17   18   43   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   49   50
CONECT   21   22   51
CONECT   22   23   23   52
CONECT   23   24
CONECT   24   25   53
CONECT   25   26   54   55
CONECT   26   27   56   57
CONECT   27   28
CONECT   28   58   59   60
END

HMDB0242295
     RDKit          3D
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydr...
 60 64  0  0  0  0  0  0  0  0999 V2000
   -4.9806    0.5289    3.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0591    0.1628    2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1520   -0.2959    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118   -1.2506    0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248    0.9329   -0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1695    1.8664    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9099    1.4818   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    0.5403    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216    0.5027   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155    0.9840   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    1.1554   -1.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.2178   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843    0.3874   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921   -0.4043    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5653   -0.2928    0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984    0.6215   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2886    1.3721    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5844    0.6240    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4989   -0.5285   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4318   -0.0534   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -1.4132    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1912   -1.5800    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -0.7776    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -0.9202    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.6323    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -1.7989    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -0.7743    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9954   -1.1721   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8936    0.8468    4.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8396   -0.9661   -0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6523    0.5460   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264    2.3346   -0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    2.4739    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.6113   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    0.7964    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    1.1017    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    1.9922   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596    0.2531   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    2.1895   -1.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    1.0131   -2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    1.1792   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322    1.3091   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4338    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4768    2.3746    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4617    1.2479    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8109    0.2516    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1502   -1.4551    0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4567   -0.6764   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0296   -0.9218   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8654    0.6412   -1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789   -2.0642    1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575   -2.3743    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2848   -1.4192   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217   -1.0706    2.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -2.6398    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201   -2.8370    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662   -1.7448    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -0.3624   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669   -2.1318   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825   -1.4168   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27  3  1  0
 27  8  1  0
 24  9  1  0
 23 12  1  0
 20 16  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
EE3cpe	HMDB
17 alpha-Ethinylestriol 3-cyclopentyl ether	HMDB
17 alpha-Ethynylestriol 3-cyclopentyl ether	HMDB
Lilly 49825	HMDB
Nylestriol	HMDB

Chemical Formula

C₂₅H₃₂O₃

Average Molecular Weight

380.528

Monoisotopic Molecular Weight

380.23514489

IUPAC Name

5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-13,14-diol

Traditional Name

5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-13,14-diol

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=C3C=CC(OC3CCCC3)=C4)C1CC(O)C2(O)C#C

InChI Identifier

InChI=1S/C25H32O3/c1-3-25(27)23(26)15-22-21-10-8-16-14-18(28-17-6-4-5-7-17)9-11-19(16)20(21)12-13-24(22,25)2/h1,9,11,14,17,20-23,26-27H,4-8,10,12-13,15H2,2H3

InChI Key

CHZJRGNDJLJLAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
16-hydroxysteroid
17-hydroxysteroid
Phenanthrene
Tetralin
Alkyl aryl ether
Ynone
Benzenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
1,2-diol
Ether
Acetylide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	4.24	ALOGPS
logP	4.32	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.63 m³·mol⁻¹	ChemAxon
Polarizability	44.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	231.658	30932474
DeepCCS	[M+Na]+	207.419	30932474
AllCCS	[M+H]+	197.7	32859911
AllCCS	[M+H-H2O]+	195.3	32859911
AllCCS	[M+NH4]+	199.8	32859911
AllCCS	[M+Na]+	200.4	32859911
AllCCS	[M-H]-	191.4	32859911
AllCCS	[M+Na-2H]-	191.8	32859911
AllCCS	[M+HCOO]-	192.5	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3349.7	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3230.3	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3753.8	Standard polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #2	C#CC1(O[Si](C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3334.4	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #2	C#CC1(O[Si](C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3262.7	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TMS,isomer #2	C#CC1(O[Si](C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3679.7	Standard polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TMS,isomer #1	C#CC1(O[Si](C)(C)C)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3337.2	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TMS,isomer #1	C#CC1(O[Si](C)(C)C)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3328.4	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TMS,isomer #1	C#CC1(O[Si](C)(C)C)C(O[Si](C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3590.8	Standard polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3591.0	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3501.4	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #1	C#CC1(O)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3912.0	Standard polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #2	C#CC1(O[Si](C)(C)C(C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3594.1	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #2	C#CC1(O[Si](C)(C)C(C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3530.5	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,1TBDMS,isomer #2	C#CC1(O[Si](C)(C)C(C)(C)C)C(O)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3804.7	Standard polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TBDMS,isomer #1	C#CC1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3813.4	Semi standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TBDMS,isomer #1	C#CC1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3824.4	Standard non polar	33892256
(16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol,2TBDMS,isomer #1	C#CC1(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC2C3CCC4=CC(OC5CCCC5)=CC=C4C3CCC21C	3783.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0094000000-44cb080d2e66471a3ef9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 10V, Positive-QTOF	splash10-000t-1069000000-478fd86c8b190f641465	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 20V, Positive-QTOF	splash10-001s-1295000000-4eceece96345c4301779	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 40V, Positive-QTOF	splash10-016u-1694000000-2d6a91e383c42b3352e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 10V, Negative-QTOF	splash10-004i-0009000000-0b10c6ff06519d7a5bd9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 20V, Negative-QTOF	splash10-004j-0049000000-3964062a5d3039a76c2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 40V, Negative-QTOF	splash10-02t9-0193000000-83d23d2b4b9934eed933	2021-10-12	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

11644606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12889492

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 (16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol (HMDB0242295)

MOL for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

3D MOL for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

3D SDF for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

3D-SDF for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

PDB for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

3D PDB for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

SMILES for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

INCHI for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

Structure for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

3D Structure for HMDB0242295 ((16R,17R)-3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra