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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015316

Secondary Accession Numbers

HMDB15316

Metabolite Identification

Common Name

Fluoxymesterone

Description

Fluoxymesterone is only found in individuals that have used or taken this drug. It is an anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem]Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.

Structure

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

1185
  Mrv0541 02231215182D          

 26 29  0  0  1  0            999 V2000
    4.1396    0.5667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555    1.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3607    0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    0.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  1  0  0  0
 12  3  1  1  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 25  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 26  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 20  1  0  0  0  0
 10 12  1  0  0  0  0
 11 17  1  0  0  0  0
 11 19  1  0  0  0  0
 11 21  1  1  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  2  0  0  0  0
 19 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
M  END

HMDB0015316
     RDKit          3D
Fluoxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.3956    1.9930    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560    0.5137    0.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5085    0.2675   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -0.2649    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968   -0.9840    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -0.2062    0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0500   -0.7934    0.4901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6638   -1.0195    1.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -1.6777    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -0.6570    0.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0271   -0.4732    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.4986    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1109    0.5113    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2694    1.4223   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.4924   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    0.1019   -0.3858 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -0.5401   -1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.3098   -0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4545    1.4744    0.4671 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    0.5019   -1.5861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1535   -0.5576   -2.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.8723   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991   -0.0545   -0.4968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5333   -1.3839   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3440    2.2848    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201    2.4899   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    2.3335    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -0.0582   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452   -1.0027    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8573    0.4241    2.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -0.8800    2.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -2.0393    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    0.8216    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -1.7389   -0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.6239    2.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -0.0226    2.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295   -2.5165    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -2.0333    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4385   -1.0617    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    2.4579   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    1.2351   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060    2.1338   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.9014    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -1.5740   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147   -0.6096   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866    0.1274   -2.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    1.3893   -2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1255   -1.4226   -2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823    1.8873   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9704    0.9463   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -2.2174   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5182   -1.2818   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941   -1.6972   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  6
 23  2  1  0
 23  6  1  0
 18  7  1  0
 16 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  6
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 20 47  1  6
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END

1185
  Mrv0541 02231215182D          

 26 29  0  0  1  0            999 V2000
    4.1396    0.5667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555    1.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3607    0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    0.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  1  0  0  0
 12  3  1  1  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 25  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 26  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 20  1  0  0  0  0
 10 12  1  0  0  0  0
 11 17  1  0  0  0  0
 11 19  1  0  0  0  0
 11 21  1  1  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  2  0  0  0  0
 19 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015316

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
YLRFCQOZQXIBAB-RBZZARIASA-N

> <FORMULA>
C20H29FO3

> <MOLECULAR_WEIGHT>
336.4409

> <EXACT_MASS>
336.210072999

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.63289533679136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.3808420980000005

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.619128292066843

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.601726563596163

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9899243323854225

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.18849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluoxymesterone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015316
     RDKit          3D
Fluoxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.3956    1.9930    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560    0.5137    0.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5085    0.2675   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -0.2649    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968   -0.9840    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -0.2062    0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0500   -0.7934    0.4901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6638   -1.0195    1.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -1.6777    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -0.6570    0.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0271   -0.4732    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.4986    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1109    0.5113    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2694    1.4223   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.4924   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    0.1019   -0.3858 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -0.5401   -1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.3098   -0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4545    1.4744    0.4671 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    0.5019   -1.5861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1535   -0.5576   -2.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.8723   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991   -0.0545   -0.4968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5333   -1.3839   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3440    2.2848    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201    2.4899   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    2.3335    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -0.0582   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452   -1.0027    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8573    0.4241    2.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -0.8800    2.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -2.0393    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    0.8216    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -1.7389   -0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.6239    2.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -0.0226    2.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295   -2.5165    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -2.0333    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4385   -1.0617    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    2.4579   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    1.2351   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060    2.1338   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.9014    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -1.5740   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147   -0.6096   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866    0.1274   -2.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    1.3893   -2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1255   -1.4226   -2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823    1.8873   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9704    0.9463   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -2.2174   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5182   -1.2818   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941   -1.6972   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  6
 23  2  1  0
 23  6  1  0
 18  7  1  0
 16 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  6
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 20 47  1  6
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1185                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       7.727   1.058   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      14.088   2.790   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.384   2.188   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -3.282   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.384   1.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.384  -0.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.051  -0.892   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.717  -0.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.841   1.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.051   2.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.316  -0.902   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.717   1.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.841  -0.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.740   0.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.075  -2.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.384   2.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.304  -2.506   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.693  -3.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.889  -0.034   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.368   3.353   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.800   0.549   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.429  -0.847   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.863  -3.353   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.416  -2.517   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      11.514  -1.347   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      11.122  -1.499   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   12                                                            
CONECT    4   24                                                            
CONECT    5    6    9   10   16                                             
CONECT    6    5    7   13   25                                             
CONECT    7    6    8   15   26                                             
CONECT    8    1    7   11   12                                             
CONECT    9    2    5   14   20                                             
CONECT   10    5   12                                                       
CONECT   11    8   17   19   21                                             
CONECT   12    3    8   10                                                  
CONECT   13    6   14                                                       
CONECT   14    9   13                                                       
CONECT   15    7   18                                                       
CONECT   16    5                                                            
CONECT   17   11   18   23                                                  
CONECT   18   15   17                                                       
CONECT   19   11   22                                                       
CONECT   20    9                                                            
CONECT   21   11                                                            
CONECT   22   19   24                                                       
CONECT   23   17   24                                                       
CONECT   24    4   22   23                                                  
CONECT   25    6                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0015316
HETATM    1  C1  UNL     1      -3.396   1.993   0.325  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.456   0.514   0.098  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.509   0.267  -0.788  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.631  -0.265   1.385  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.297  -0.984   1.633  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.376  -0.206   0.791  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.050  -0.793   0.490  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.664  -1.019   1.829  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.981  -1.678   1.467  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.754  -0.657   0.711  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.027  -0.473   1.085  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.885   0.499   0.420  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.111   0.511   0.694  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.269   1.422  -0.545  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.791   1.492  -0.369  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.141   0.102  -0.386  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.590  -0.540  -1.686  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.684   0.310  -0.283  1.00  0.00           C  
HETATM   19  F1  UNL     1       0.454   1.474   0.467  1.00  0.00           F  
HETATM   20  C17 UNL     1      -0.027   0.502  -1.586  1.00  0.00           C  
HETATM   21  O3  UNL     1       0.153  -0.558  -2.465  1.00  0.00           O  
HETATM   22  C18 UNL     1      -1.460   0.872  -1.387  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.199  -0.054  -0.497  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.533  -1.384  -1.105  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.344   2.285   0.833  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.420   2.490  -0.665  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.578   2.334   0.957  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.270  -0.058  -0.263  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.445  -1.003   1.335  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.857   0.424   2.213  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.038  -0.880   2.701  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.349  -2.039   1.301  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.227   0.822   1.180  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.048  -1.739  -0.050  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.039  -1.624   2.485  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.936  -0.023   2.278  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.729  -2.516   0.782  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.509  -2.033   2.355  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.439  -1.062   1.907  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.661   2.458  -0.320  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.583   1.235  -1.597  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.306   2.134  -1.107  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.589   1.901   0.646  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.245  -1.574  -1.801  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.715  -0.610  -1.606  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.387   0.127  -2.522  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.466   1.389  -2.085  1.00  0.00           H  
HETATM   48  H24 UNL     1      -0.126  -1.423  -2.130  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.482   1.887  -0.925  1.00  0.00           H  
HETATM   50  H26 UNL     1      -1.970   0.946  -2.374  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.908  -2.217  -0.737  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.518  -1.282  -2.216  1.00  0.00           H  
HETATM   53  H29 UNL     1      -3.594  -1.697  -0.873  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   23
CONECT    3   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   23   33
CONECT    7    8   18   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   11   16
CONECT   11   12   39
CONECT   12   13   13   14
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   18
CONECT   17   44   45   46
CONECT   18   19   20
CONECT   20   21   22   47
CONECT   21   48
CONECT   22   23   49   50
CONECT   23   24
CONECT   24   51   52   53
END

HMDB0015316
     RDKit          3D
Fluoxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.3956    1.9930    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4560    0.5137    0.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5085    0.2675   -0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -0.2649    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968   -0.9840    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -0.2062    0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0500   -0.7934    0.4901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6638   -1.0195    1.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -1.6777    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538   -0.6570    0.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0271   -0.4732    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845    0.4986    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1109    0.5113    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2694    1.4223   -0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.4924   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    0.1019   -0.3858 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -0.5401   -1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    0.3098   -0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4545    1.4744    0.4671 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    0.5019   -1.5861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1535   -0.5576   -2.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.8723   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991   -0.0545   -0.4968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5333   -1.3839   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3440    2.2848    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4201    2.4899   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    2.3335    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -0.0582   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452   -1.0027    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8573    0.4241    2.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -0.8800    2.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -2.0393    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    0.8216    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -1.7389   -0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.6239    2.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -0.0226    2.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7295   -2.5165    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -2.0333    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4385   -1.0617    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610    2.4579   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    1.2351   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060    2.1338   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.9014    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -1.5740   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147   -0.6096   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866    0.1274   -2.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4659    1.3893   -2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1255   -1.4226   -2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823    1.8873   -0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9704    0.9463   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -2.2174   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5182   -1.2818   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941   -1.6972   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  6
 23  2  1  0
 23  6  1  0
 18  7  1  0
 16 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  1
  7 34  1  6
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 20 47  1  6
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one	ChEBI
17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone	ChEBI
9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one	ChEBI
9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone	ChEBI
Fluoximesterona	ChEBI
Fluoxymesteronum	ChEBI
Androxy	Kegg
Halotestin	Kegg
11b,17b-Dihydroxy-9a-fluoro-17a-methyl-4-androster-3-one	Generator
11Β,17β-dihydroxy-9α-fluoro-17α-methyl-4-androster-3-one	Generator
17a-Methyl-9a-fluoro-11b-hydroxytesterone	Generator
17Α-methyl-9α-fluoro-11β-hydroxytesterone	Generator
9-Fluoro-11b,17b-dihydroxy-17-methylandrost-4-en-3-one	Generator
9-Fluoro-11β,17β-dihydroxy-17-methylandrost-4-en-3-one	Generator
9a-Fluoro-11b-hydroxy-17-methyltestosterone	Generator
9Α-fluoro-11β-hydroxy-17-methyltestosterone	Generator
Androfluorene	HMDB
Androfluorone	HMDB
Fluossimesterone	HMDB
Fluoximesterone	HMDB
Fluoximesteronum	HMDB
Fluoxymestrone	HMDB
Fluoximesteron	HMDB
Android-F	HMDB
Android F	HMDB
Atlantis brand OF fluoxymesterone	HMDB
Pharmacia brand OF fluoxymesterone	HMDB
Stenox	HMDB

Chemical Formula

C₂₀H₂₉FO₃

Average Molecular Weight

336.4409

Monoisotopic Molecular Weight

336.210072999

IUPAC Name

(1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

fluoxymesterone

CAS Registry Number

76-43-7

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1

InChI Key

YLRFCQOZQXIBAB-RBZZARIASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
9-halo-steroid
Halo-steroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Fluorohydrin
Halohydrin
Ketone
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Organooxygen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:5120 )
3-oxo Delta(4)-steroid (CHEBI:5120 )
17beta-hydroxy steroid (CHEBI:5120 )
fluorinated steroid (CHEBI:5120 )
anabolic androgenic steroid (CHEBI:5120 )
C19 steroids (androgens) and derivatives (LMST02020025 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antineoplastic agent (HMDB: HMDB0015316)

Biological role

anabolic agent (HMDB: HMDB0015316)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	270 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.045 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.38	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	36.63 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]-	212.495	30932474
DeepCCS	[M+Na]+	187.622	30932474
AllCCS	[M+H]+	182.7	32859911
AllCCS	[M+H-H2O]+	179.9	32859911
AllCCS	[M+NH4]+	185.3	32859911
AllCCS	[M+Na]+	186.0	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	187.5	32859911
AllCCS	[M+HCOO]-	188.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluoxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3870.8	Standard polar	33892256
Fluoxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2690.6	Standard non polar	33892256
Fluoxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2648.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluoxymesterone,1TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	2964.5	Semi standard non polar	33892256
Fluoxymesterone,1TMS,isomer #2	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2920.1	Semi standard non polar	33892256
Fluoxymesterone,1TMS,isomer #3	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	2843.4	Semi standard non polar	33892256
Fluoxymesterone,2TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2912.6	Semi standard non polar	33892256
Fluoxymesterone,2TMS,isomer #2	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	2832.7	Semi standard non polar	33892256
Fluoxymesterone,2TMS,isomer #3	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2779.5	Semi standard non polar	33892256
Fluoxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2776.1	Semi standard non polar	33892256
Fluoxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2902.1	Standard non polar	33892256
Fluoxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2836.0	Standard polar	33892256
Fluoxymesterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3208.7	Semi standard non polar	33892256
Fluoxymesterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(C)O)[C@@H]2CCC3=CC(=O)CC[C@]3(C)[C@@]12F	3164.6	Semi standard non polar	33892256
Fluoxymesterone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)C[C@H](O)[C@@]12F	3099.2	Semi standard non polar	33892256
Fluoxymesterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(C)O[Si](C)(C)C(C)(C)C)[C@@H]2CCC3=CC(=O)CC[C@]3(C)[C@@]12F	3374.9	Semi standard non polar	33892256
Fluoxymesterone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O)[C@@]12F	3294.3	Semi standard non polar	33892256
Fluoxymesterone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]12F	3224.9	Semi standard non polar	33892256
Fluoxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]12F	3411.5	Semi standard non polar	33892256
Fluoxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]12F	3593.5	Standard non polar	33892256
Fluoxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]12F	3114.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxymesterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1934000000-8eb342128d6bf9311319	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxymesterone GC-MS (2 TMS) - 70eV, Positive	splash10-00ou-0951400000-91106f5e4565733878fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxymesterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-5951000000-4c37d94fe4ed0b343941	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 10V, Positive-QTOF	splash10-014r-0019000000-48934627a15489915ee8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 20V, Positive-QTOF	splash10-014r-0289000000-97f81d1c3434cd2ebf78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 40V, Positive-QTOF	splash10-0udi-3294000000-6727e66346d908d21d94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 10V, Negative-QTOF	splash10-000i-0009000000-8fa1a3bcb20d7e11f56c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 20V, Negative-QTOF	splash10-00kr-0009000000-e763c698cec90ff489d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 40V, Negative-QTOF	splash10-00mo-0596000000-4dd2e6ac91164ea740ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 10V, Positive-QTOF	splash10-00kr-0019000000-e06c0ac56f323c20416a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 20V, Positive-QTOF	splash10-004u-2594000000-7ce7c92338e057214383	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 40V, Positive-QTOF	splash10-05ec-5940000000-063fa6a84fc098f79fca	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 10V, Negative-QTOF	splash10-000i-0009000000-f77bab0fc5505f2a76bd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 20V, Negative-QTOF	splash10-000i-0029000000-47936a6dd33f48e53957	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxymesterone 40V, Negative-QTOF	splash10-014r-2239000000-4e814ffc32e746f27d3f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01185	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01185	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01185

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluoxymesterone

METLIN ID

Not Available

PubChem Compound

6446

PDB ID

Not Available

ChEBI ID

5120

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)

Download (PDF)

General References

Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. [PubMed:17023534 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Fernandez L, Chirino R, Boada LD, Navarro D, Cabrera N, del Rio I, Diaz-Chico BN: Stanozolol and danazol, unlike natural androgens, interact with the low affinity glucocorticoid-binding sites from male rat liver microsomes. Endocrinology. 1994 Mar;134(3):1401-8. [PubMed:8119180 ]
Kasperk CH, Wergedal JE, Farley JR, Linkhart TA, Turner RT, Baylink DJ: Androgens directly stimulate proliferation of bone cells in vitro. Endocrinology. 1989 Mar;124(3):1576-8. [PubMed:2521824 ]
Smallridge RC, Vigersky R, Glass AR, Griffin JE, White BJ, Eil C: Androgen receptor abnormalities in identical twins with oligospermia. Clinical and biochemical studies. Am J Med. 1984 Dec;77(6):1049-54. [PubMed:6439037 ]
Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. [PubMed:17023534 ]
Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM: Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Mol Endocrinol. 1999 Mar;13(3):440-54. [PubMed:10077001 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Ingle JN, Suman VJ, Mailliard JA, Kugler JW, Krook JE, Michalak JC, Pisansky TM, Wold LE, Donohue JH, Goetz MP, Perez EA: Randomized trial of tamoxifen alone or combined with fluoxymesterone as adjuvant therapy in postmenopausal women with resected estrogen receptor positive breast cancer. North Central Cancer Treatment Group Trial 89-30-52. Breast Cancer Res Treat. 2006 Jul;98(2):217-22. Epub 2006 Mar 15. [PubMed:16538529 ]
Sledge GW Jr, Hu P, Falkson G, Tormey D, Abeloff M: Comparison of chemotherapy with chemohormonal therapy as first-line therapy for metastatic, hormone-sensitive breast cancer: An Eastern Cooperative Oncology Group study. J Clin Oncol. 2000 Jan;18(2):262-6. [PubMed:10637238 ]
Pearson OH, Manni A, Arafah BM: Antiestrogen treatment of breast cancer: an overview. Cancer Res. 1982 Aug;42(8 Suppl):3424s-3429s. [PubMed:7044524 ]
Perloff M, Norton L, Korzun AH, Wood WC, Carey RW, Gottlieb A, Aust JC, Bank A, Silver RT, Saleh F, Canellos GP, Perry MC, Weiss RB, Holland JF: Postsurgical adjuvant chemotherapy of stage II breast carcinoma with or without crossover to a non-cross-resistant regimen: a Cancer and Leukemia Group B study. J Clin Oncol. 1996 May;14(5):1589-98. [PubMed:8622076 ]
Swain SM, Steinberg SM, Bagley C, Lippman ME: Tamoxifen and fluoxymesterone versus tamoxifen and danazol in metastatic breast cancer--a randomized study. Breast Cancer Res Treat. 1988 Sep;12(1):51-7. [PubMed:3058238 ]

Showing metabocard for Fluoxymesterone (HMDB0015316)

MOL for HMDB0015316 (Fluoxymesterone)

3D MOL for HMDB0015316 (Fluoxymesterone)

3D SDF for HMDB0015316 (Fluoxymesterone)

3D-SDF for HMDB0015316 (Fluoxymesterone)

PDB for HMDB0015316 (Fluoxymesterone)

3D PDB for HMDB0015316 (Fluoxymesterone)

SMILES for HMDB0015316 (Fluoxymesterone)

INCHI for HMDB0015316 (Fluoxymesterone)

Structure for HMDB0015316 (Fluoxymesterone)

3D Structure for HMDB0015316 (Fluoxymesterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References