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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:54:19 UTC

Update Date

2021-09-26 22:52:44 UTC

HMDB ID

HMDB0244769

Secondary Accession Numbers

None

Metabolite Identification

Common Name

17-Ethynyl-16-fluoroestradiol

Description

17-Ethynyl-16-fluoroestradiol 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 17-Ethynyl-16-fluoroestradiol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 17-ethynyl-16-fluoroestradiol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 17-Ethynyl-16-fluoroestradiol 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

HMDB0244769
     RDKit          3D
17-Ethynyl-16-fluoroestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.4809    1.4865    2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554    0.9515    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    0.3044    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945    0.6959   -0.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637   -1.1886    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475   -1.5317    1.3220 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491   -1.6592    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303   -0.7673   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2349   -0.7608   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263   -2.1417   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -2.2324    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905   -0.9077    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225   -0.7887   -0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.4687   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    0.5583   -0.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847    1.5903    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.4564    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.2217    0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.0494    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.0656    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.6082    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.5739   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592    1.0903   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064    1.9587    3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    1.5086   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -1.6450   -0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9271   -2.7246   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -1.5394    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472   -1.2289   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -0.2254   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -2.8807   -0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -2.5436   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201   -2.4801    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -2.9947   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110   -1.6777   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250    1.4719   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    2.5638    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981    2.3730    0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -0.8662    1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    0.7403    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.8946    1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937    2.2787    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5264    2.2487   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    0.4274   -2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.0803   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    1.2158   -2.5910 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22  3  1  0
 22  8  1  0
 19  9  1  0
 18 12  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END


  Mrv1533004241523582D          

 23 26  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 F   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
  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
M  END
> <DATABASE_ID>
HMDB0244769

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H23FO2/c1-3-20(23)18(21)11-17-16-6-4-12-10-13(22)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,22-23H,4,6,8-9,11H2,2H3

> <INCHI_KEY>
IFDRGXJMFGLUCN-UHFFFAOYSA-N

> <FORMULA>
C20H23FO2

> <MOLECULAR_WEIGHT>
314.4

> <EXACT_MASS>
314.168208144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.5623657379238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethynyl-13-fluoro-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.713541255000001

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.773247795208471

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.311216208116189

> <JCHEM_PKA_STRONGEST_BASIC>
-4.217105334419032

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
87.04390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethynyl-13-fluoro-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244769
     RDKit          3D
17-Ethynyl-16-fluoroestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.4809    1.4865    2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554    0.9515    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    0.3044    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945    0.6959   -0.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637   -1.1886    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475   -1.5317    1.3220 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491   -1.6592    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303   -0.7673   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2349   -0.7608   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263   -2.1417   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -2.2324    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905   -0.9077    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225   -0.7887   -0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.4687   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    0.5583   -0.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847    1.5903    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.4564    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.2217    0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.0494    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.0656    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.6082    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.5739   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592    1.0903   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064    1.9587    3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    1.5086   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -1.6450   -0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9271   -2.7246   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -1.5394    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472   -1.2289   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -0.2254   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -2.8807   -0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -2.5436   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201   -2.4801    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -2.9947   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110   -1.6777   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250    1.4719   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    2.5638    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981    2.3730    0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -0.8662    1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    0.7403    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.8946    1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937    2.2787    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5264    2.2487   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    0.4274   -2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.0803   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    1.2158   -2.5910 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22  3  1  0
 22  8  1  0
 19  9  1  0
 18 12  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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  F   UNK     0      10.813   1.738   0.000  0.00  0.00           F+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
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                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0244769
HETATM    1  C1  UNL     1      -3.481   1.487   2.374  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.355   0.951   1.305  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.228   0.304   0.001  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.294   0.696  -0.844  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.364  -1.189   0.164  1.00  0.00           C  
HETATM    6  F1  UNL     1      -4.048  -1.532   1.322  1.00  0.00           F  
HETATM    7  C5  UNL     1      -1.949  -1.659   0.246  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.230  -0.767  -0.766  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.235  -0.761  -0.585  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.826  -2.142  -0.591  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.169  -2.232   0.101  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.890  -0.908   0.107  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.222  -0.789  -0.159  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.817   0.469  -0.137  1.00  0.00           C  
HETATM   15  O2  UNL     1       6.191   0.558  -0.414  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.085   1.590   0.148  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.719   1.456   0.418  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.137   0.222   0.396  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.710  -0.049   0.660  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.131   1.066   1.093  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.080   1.608   0.069  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.886   0.574  -0.645  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.159   1.090  -2.045  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.606   1.959   3.332  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.692   1.509  -0.434  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.930  -1.645  -0.672  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.927  -2.725  -0.072  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.544  -1.539   1.264  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.447  -1.229  -1.754  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.683  -0.225  -1.465  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.161  -2.881  -0.066  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.958  -2.544  -1.612  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.020  -2.480   1.182  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.806  -2.995  -0.381  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.811  -1.678  -0.386  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.625   1.472  -0.398  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.555   2.564   0.163  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.198   2.373   0.630  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.732  -0.866   1.450  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.704   0.740   2.020  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.485   1.895   1.476  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.794   2.279   0.596  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.526   2.249  -0.649  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.852   0.427  -2.591  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.616   2.080  -1.950  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.192   1.216  -2.591  1.00  0.00           H  
CONECT    1    2    2    2   24
CONECT    2    3
CONECT    3    4    5   22
CONECT    4   25
CONECT    5    6    7   26
CONECT    7    8   27   28
CONECT    8    9   22   29
CONECT    9   10   19   30
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   13   18
CONECT   13   14   35
CONECT   14   15   16   16
CONECT   15   36
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19
CONECT   19   20   39
CONECT   20   21   40   41
CONECT   21   22   42   43
CONECT   22   23
CONECT   23   44   45   46
END

HMDB0244769
     RDKit          3D
17-Ethynyl-16-fluoroestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.4809    1.4865    2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554    0.9515    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    0.3044    0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945    0.6959   -0.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637   -1.1886    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0475   -1.5317    1.3220 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491   -1.6592    0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303   -0.7673   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2349   -0.7608   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263   -2.1417   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -2.2324    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905   -0.9077    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225   -0.7887   -0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    0.4687   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1915    0.5583   -0.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847    1.5903    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.4564    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.2217    0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.0494    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.0656    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798    1.6082    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.5739   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592    1.0903   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064    1.9587    3.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    1.5086   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -1.6450   -0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9271   -2.7246   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440   -1.5394    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472   -1.2289   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -0.2254   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -2.8807   -0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -2.5436   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201   -2.4801    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -2.9947   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110   -1.6777   -0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250    1.4719   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    2.5638    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981    2.3730    0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -0.8662    1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    0.7403    2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850    1.8946    1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937    2.2787    0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5264    2.2487   -0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    0.4274   -2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164    2.0803   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    1.2158   -2.5910 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22  3  1  0
 22  8  1  0
 19  9  1  0
 18 12  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃FO₂

Average Molecular Weight

314.4

Monoisotopic Molecular Weight

314.168208144

IUPAC Name

14-ethynyl-13-fluoro-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol

Traditional Name

14-ethynyl-13-fluoro-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H23FO2/c1-3-20(23)18(21)11-17-16-6-4-12-10-13(22)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,22-23H,4,6,8-9,11H2,2H3

InChI Key

IFDRGXJMFGLUCN-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
3-hydroxysteroid
16-halo-steroid
Halo-steroid
17-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ynone
Cyclic alcohol
Tertiary alcohol
Halohydrin
Fluorohydrin
Acetylide
Organofluoride
Organohalogen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Alkyl halide
Alkyl fluoride
Organooxygen 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	3.46	ALOGPS
logP	3.71	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	10.31	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.04 m³·mol⁻¹	ChemAxon
Polarizability	34.56 Å³	ChemAxon
Number of Rings	4	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]-	211.855	30932474
DeepCCS	[M+Na]+	187.42	30932474
AllCCS	[M+H]+	178.1	32859911
AllCCS	[M+H-H2O]+	174.9	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	181.9	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	182.8	32859911
AllCCS	[M+HCOO]-	182.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.0154 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2299.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	364.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	445.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	760.6 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	714.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1341.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.0 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	1525.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	443.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	314.6 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	33.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17-Ethynyl-16-fluoroestradiol	CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(F)C2(O)C#C	4232.7	Standard polar	33892256
17-Ethynyl-16-fluoroestradiol	CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(F)C2(O)C#C	2679.6	Standard non polar	33892256
17-Ethynyl-16-fluoroestradiol	CC12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(F)C2(O)C#C	2663.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-0390000000-f536398e2d765253a202	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-Ethynyl-16-fluoroestradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 17-Ethynyl-16-fluoroestradiol 10V, Positive-QTOF	splash10-014i-0029000000-83aac8c3f6c41e778ca8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Ethynyl-16-fluoroestradiol 20V, Positive-QTOF	splash10-00kr-0693000000-e24e55f584061bf85412	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Ethynyl-16-fluoroestradiol 40V, Positive-QTOF	splash10-03fr-0980000000-68b7140b9336f75ff328	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Ethynyl-16-fluoroestradiol 10V, Negative-QTOF	splash10-03dl-0079000000-9004d416060a31788070	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Ethynyl-16-fluoroestradiol 20V, Negative-QTOF	splash10-03di-0097000000-d6da1694e0e8600bfd52	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-Ethynyl-16-fluoroestradiol 40V, Negative-QTOF	splash10-0cdl-2392000000-b6cb73d7787ba0d7338c	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

26502284

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14728728

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 17-Ethynyl-16-fluoroestradiol (HMDB0244769)

MOL for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

3D MOL for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

3D SDF for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

3D-SDF for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

PDB for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

3D PDB for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

SMILES for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

INCHI for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

Structure for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

3D Structure for HMDB0244769 (17-Ethynyl-16-fluoroestradiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra