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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 22:34:37 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004626

Secondary Accession Numbers

HMDB04626

Metabolite Identification

Common Name

Tetrahydrogestrinone

Description

The identification of tetrahydrogestrinone (THG), the first true "designer androgen," as a sports doping agent reflects both an alarmingly sophisticated illicit manufacturing facility and an underground network of androgen abusers in elite sports, as well as the still untapped potential for designer androgens in medicine. Never marketed, THG was apparently developed as a potent androgen that was undetectable by conventional International Olympic Committee-mandated urinary sports doping tests. As a potent androgen and progestin with unspecified contaminants, its distribution for use at high doses without any prior biological or toxicological evaluation poses significant health risks. Yet this diversion of science also highlights the prospect of designer androgens for use in human medicine. Designer androgens also offer the possibility of tissue-specific effects enhancing the beneficial effects of androgens while mitigating the undesirable ones. Further developments require better understanding of the post receptor tissue selectivity of androgens, comparable to the mechanism underlying that of partial estrogen agonists (SERMs). This experience highlights the ongoing need for vigilance to detect novel drug doping strategies in order to maintain fairness and safety in elite sports. This will require the deployment of generic catch-all tests, such as sensitive and specific in vitro androgen bioassays, coupled with the development of mass spectrometry-based tests for specific doping agents. Starting from gestrinone, chemists can synthesize THG in one reaction step. (PMID: 15934041 , 15292520 ).

Structure

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

  Mrv0541 02231219572D          

 25 28  0  0  1  0            999 V2000
   10.4746   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4746   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7601   -7.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7601   -9.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9036   -7.8095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9036   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890   -7.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890   -9.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6182   -6.5720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6182   -7.3970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9036   -6.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1892   -6.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3329   -6.1493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0555   -6.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0461   -7.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5987   -5.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5987   -8.1381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8995   -7.0474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4737   -8.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -5.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7733   -5.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1373   -5.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -5.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  2  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  2  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  6  5  1  0  0  0  0
 11 18  1  1  0  0  0
 12 19  1  6  0  0  0
  7 20  1  1  0  0  0
  6 21  2  0  0  0  0
 15 22  1  6  0  0  0
 15 23  1  1  0  0  0
 18 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END

HMDB0004626
     RDKit          3D
Tetrahydrogestrinone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0672    1.7597    0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    0.3758    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260   -0.3819    0.3049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5323   -0.4419   -0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638   -1.8732    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -2.3071    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061   -1.0415    0.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7390   -0.9522   -0.0111 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7354   -1.9605    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -1.8329   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -0.3857   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -0.0475   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8481    1.3741   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.7551   -1.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    2.4254   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1459    1.9012    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.6406    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.4045    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239    1.3830    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.2703    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.0803    0.0769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2094    0.4663   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -0.5605   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666    1.8406    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    2.5399    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554    2.1272   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.4821    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -0.1615    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093   -0.8183   -0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486   -1.8708    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123   -2.4796    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -2.9406    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -2.9904   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292   -0.8353    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -1.0833   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3218   -2.9679    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -1.7217    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -2.3918    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -2.2760   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.8027   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943    3.3334   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    2.6577   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.6443    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    1.6515    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    2.2151    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.9754    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.9750   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115    1.3015   -1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -1.5786   -2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -0.2879   -3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -0.5887   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  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  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

  Mrv0541 02231219572D          

 25 28  0  0  1  0            999 V2000
   10.4746   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4746   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7601   -7.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7601   -9.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9036   -7.8095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9036   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890   -7.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890   -9.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6182   -6.5720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6182   -7.3970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9036   -6.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1892   -6.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3329   -6.1493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0555   -6.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0461   -7.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5987   -5.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5987   -8.1381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8995   -7.0474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4737   -8.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -5.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7733   -5.5652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1373   -5.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -5.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  2  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  2  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  6  5  1  0  0  0  0
 11 18  1  1  0  0  0
 12 19  1  6  0  0  0
  7 20  1  1  0  0  0
  6 21  2  0  0  0  0
 15 22  1  6  0  0  0
 15 23  1  1  0  0  0
 18 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004626

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h9,11,13,18-19,23H,3-8,10,12H2,1-2H3/t18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
OXHNQTSIKGHVBH-ANULTFPQSA-N

> <FORMULA>
C21H28O2

> <MOLECULAR_WEIGHT>
312.4458

> <EXACT_MASS>
312.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.020863814178554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.5018849433333337

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.903249710660603

> <JCHEM_PKA_STRONGEST_BASIC>
-0.14423085676789704

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
95.41789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrogestrinone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0004626
     RDKit          3D
Tetrahydrogestrinone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0672    1.7597    0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    0.3758    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260   -0.3819    0.3049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5323   -0.4419   -0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638   -1.8732    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -2.3071    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061   -1.0415    0.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7390   -0.9522   -0.0111 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7354   -1.9605    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -1.8329   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -0.3857   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -0.0475   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8481    1.3741   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.7551   -1.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    2.4254   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1459    1.9012    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.6406    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.4045    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239    1.3830    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.2703    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.0803    0.0769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2094    0.4663   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -0.5605   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666    1.8406    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    2.5399    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554    2.1272   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.4821    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -0.1615    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093   -0.8183   -0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486   -1.8708    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123   -2.4796    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -2.9406    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -2.9904   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292   -0.8353    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -1.0833   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3218   -2.9679    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -1.7217    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -2.3918    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -2.2760   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.8027   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943    3.3334   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    2.6577   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.6443    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    1.6515    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    2.2151    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.9754    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.9750   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115    1.3015   -1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -1.5786   -2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -0.2879   -3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -0.5887   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  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  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      19.553 -14.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.553 -16.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.219 -13.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.219 -16.888   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.885 -14.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.885 -16.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.220 -14.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.220 -16.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.886 -13.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.886 -16.888   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.554 -12.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.554 -13.808   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.220 -11.498   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.887 -12.268   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.888 -11.479   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.237 -12.307   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.219 -13.814   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.518 -11.067   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      23.518 -15.191   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      22.212 -13.155   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      15.818 -16.783   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      24.405 -10.597   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.710 -10.388   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.656 -10.493   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.405  -9.631   0.000  0.00  0.00           C+0
CONECT    1    3    9    2                                                  
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   21                                                  
CONECT    7    8   12    9   20                                             
CONECT    8    7   10                                                       
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   18                                             
CONECT   12    7   11   17   19                                             
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   22   23                                             
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   11   24                                                       
CONECT   19   12                                                            
CONECT   20    7                                                            
CONECT   21    6                                                            
CONECT   22   15   25                                                       
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0004626
HETATM    1  C1  UNL     1      -4.067   1.760   0.775  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.709   0.376   1.231  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.826  -0.382   0.305  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.532  -0.442  -0.930  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.764  -1.873   0.735  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.342  -2.307   0.551  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.606  -1.041   0.607  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.739  -0.952  -0.011  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.735  -1.961   0.581  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.991  -1.833  -0.246  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.381  -0.386  -0.314  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.535  -0.047  -0.924  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.848   1.374  -0.952  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.017   1.755  -1.300  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.861   2.425  -0.589  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.146   1.901   0.648  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.532   0.641   0.268  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.249   0.404   0.429  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.324   1.383   1.006  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.002   1.270   0.864  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.463   0.080   0.077  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.209   0.466  -1.353  1.00  0.00           C  
HETATM   23  C21 UNL     1      -1.397  -0.560  -2.387  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.167   1.841   0.541  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.935   2.540   1.583  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.555   2.127  -0.109  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.182   0.482   2.206  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.679  -0.162   1.430  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.409  -0.818  -0.723  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.049  -1.871   1.820  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.512  -2.480   0.223  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.099  -2.941   1.465  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.150  -2.990  -0.280  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.429  -0.835   1.715  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.799  -1.083  -1.093  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.322  -2.968   0.441  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.951  -1.722   1.629  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.796  -2.392   0.310  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.881  -2.276  -1.250  1.00  0.00           H  
HETATM   40  H17 UNL     1       5.174  -0.803  -1.361  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.394   3.333  -0.280  1.00  0.00           H  
HETATM   42  H19 UNL     1       3.159   2.658  -1.409  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.582   2.644   1.173  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.005   1.652   1.351  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.731   2.215   1.562  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.666   1.975   1.286  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.202   0.975  -1.438  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.912   1.301  -1.577  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.604  -1.579  -2.104  1.00  0.00           H  
HETATM   50  H27 UNL     1      -2.209  -0.288  -3.134  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.477  -0.589  -3.046  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    5   21
CONECT    4   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   21   34
CONECT    8    9   18   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   12   17
CONECT   12   13   40
CONECT   13   14   14   15
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   18
CONECT   18   19
CONECT   19   20   20   45
CONECT   20   21   46
CONECT   21   22
CONECT   22   23   47   48
CONECT   23   49   50   51
END

HMDB0004626
     RDKit          3D
Tetrahydrogestrinone
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0672    1.7597    0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    0.3758    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8260   -0.3819    0.3049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5323   -0.4419   -0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638   -1.8732    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -2.3071    0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061   -1.0415    0.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7390   -0.9522   -0.0111 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7354   -1.9605    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -1.8329   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -0.3857   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -0.0475   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8481    1.3741   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    1.7551   -1.3002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    2.4254   -0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1459    1.9012    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318    0.6406    0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486    0.4045    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3239    1.3830    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024    1.2703    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4629    0.0803    0.0769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2094    0.4663   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3967   -0.5605   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666    1.8406    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    2.5399    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554    2.1272   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.4821    2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -0.1615    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093   -0.8183   -0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486   -1.8708    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123   -2.4796    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -2.9406    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -2.9904   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292   -0.8353    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -1.0833   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3218   -2.9679    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -1.7217    1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7963   -2.3918    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -2.2760   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -0.8027   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943    3.3334   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588    2.6577   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.6443    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0047    1.6515    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    2.2151    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    1.9754    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.9750   -1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115    1.3015   -1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -1.5786   -2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -0.2879   -3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -0.5887   -3.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  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  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-3-one	HMDB
THG	HMDB
Tetrahydrogestrinone	MeSH
17-HYDROXY-18a-homo-19-nor-17a-pregna-4,9,11-trien-3-one	Generator, HMDB
17-HYDROXY-18a-homo-19-nor-17α-pregna-4,9,11-trien-3-one	Generator, HMDB

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Weight

312.4458

Monoisotopic Molecular Weight

312.20893014

IUPAC Name

(10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one

Traditional Name

tetrahydrogestrinone

CAS Registry Number

618903-56-3

SMILES

[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h9,11,13,18-19,23H,3-8,10,12H2,1-2H3/t18-,19+,20+,21+/m1/s1

InChI Key

OXHNQTSIKGHVBH-ANULTFPQSA-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-oxosteroid
Hydroxysteroid
17-hydroxysteroid
Oxosteroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004626)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004626)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004626)

Source

Exogenous

Exogenous (HMDB: HMDB0004626)

Food

Food (HMDB: HMDB0004626)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004626)

Molecular messenger

Hormone (HMDB: HMDB0004626)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004626)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0004626)

Physical Properties

State

Solid

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
Water Solubility	0.02 g/L	ALOGPS
logP	3.95	ALOGPS
logP	3.5	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.9	ChemAxon
pKa (Strongest Basic)	-0.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.42 m³·mol⁻¹	ChemAxon
Polarizability	37.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.707	31661259
DarkChem	[M-H]-	170.434	31661259
DeepCCS	[M-2H]-	207.98	30932474
DeepCCS	[M+Na]+	182.986	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	183.0	32859911
AllCCS	[M+Na]+	183.8	32859911
AllCCS	[M-H]-	185.6	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	186.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrogestrinone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]	4160.4	Standard polar	33892256
Tetrahydrogestrinone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]	2863.3	Standard non polar	33892256
Tetrahydrogestrinone	[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]	2879.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrogestrinone,1TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21CC	2947.6	Semi standard non polar	33892256
Tetrahydrogestrinone,1TMS,isomer #2	CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC	2952.7	Semi standard non polar	33892256
Tetrahydrogestrinone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC	2978.0	Semi standard non polar	33892256
Tetrahydrogestrinone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC	2975.4	Standard non polar	33892256
Tetrahydrogestrinone,2TMS,isomer #1	CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC	3315.3	Standard polar	33892256
Tetrahydrogestrinone,1TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21CC	3203.8	Semi standard non polar	33892256
Tetrahydrogestrinone,1TBDMS,isomer #2	CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC	3187.1	Semi standard non polar	33892256
Tetrahydrogestrinone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC	3473.4	Semi standard non polar	33892256
Tetrahydrogestrinone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC	3489.0	Standard non polar	33892256
Tetrahydrogestrinone,2TBDMS,isomer #1	CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC	3511.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrogestrinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1190000000-df8a155fb516cec4576a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrogestrinone GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-2029000000-895175c474d195f98cc4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrogestrinone 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 - Tetrahydrogestrinone 10V, Positive-QTOF	splash10-01ot-0095000000-8cbb62095c5e14373a79	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 20V, Positive-QTOF	splash10-01ot-0191000000-e69b0d42106f07a3727c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 40V, Positive-QTOF	splash10-0umi-1490000000-96c8e821e03405188c49	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 10V, Negative-QTOF	splash10-03di-0029000000-c002fd210563a9508a67	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 20V, Negative-QTOF	splash10-03di-0089000000-1b89e06ba01d60280bdd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 40V, Negative-QTOF	splash10-00lr-0090000000-e424a28e9a87e909dcf0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 10V, Negative-QTOF	splash10-03di-0009000000-152b659b4891e36b54f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 20V, Negative-QTOF	splash10-03di-0029000000-5372cd42b1affac2ac15	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 40V, Negative-QTOF	splash10-014i-0091000000-94f3485bb8e82ec323c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 10V, Positive-QTOF	splash10-03di-0059000000-a33ccf5f4a2ed5241d04	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 20V, Positive-QTOF	splash10-014i-0490000000-e755336609970c5c9e52	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrogestrinone 40V, Positive-QTOF	splash10-00te-1930000000-224c330abfdea1cfae22	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06870

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023385

KNApSAcK ID

Not Available

Chemspider ID

5257020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrahydrogestrinone

METLIN ID

Not Available

PubChem Compound

6857686

PDB ID

17H

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

Labrie, Fernand; Luu-The, Van; Calvo, Ezequiel; Martel, Celine; Cloutier, Julie; Gauthier, Sylvain; Belleau, Pascal; Morissette, Jean; Levesque, Marie-Helene; Labrie, Claude. Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid. J Endocrinol. 2005 Feb;184(2):427-33. Pubmed: 15684350

Material Safety Data Sheet (MSDS)

Not Available

General References

Thevis M, Geyer H, Mareck U, Schanzer W: Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2005 Jul;40(7):955-62. [PubMed:15934041 ]
Handelsman DJ: Designer androgens in sport: when too much is never enough. Sci STKE. 2004 Jul 27;2004(244):pe41. [PubMed:15292520 ]

Showing metabocard for Tetrahydrogestrinone (HMDB0004626)

MOL for HMDB0004626 (Tetrahydrogestrinone)

3D MOL for HMDB0004626 (Tetrahydrogestrinone)

3D SDF for HMDB0004626 (Tetrahydrogestrinone)

3D-SDF for HMDB0004626 (Tetrahydrogestrinone)

PDB for HMDB0004626 (Tetrahydrogestrinone)

3D PDB for HMDB0004626 (Tetrahydrogestrinone)

SMILES for HMDB0004626 (Tetrahydrogestrinone)

INCHI for HMDB0004626 (Tetrahydrogestrinone)

Structure for HMDB0004626 (Tetrahydrogestrinone)

3D Structure for HMDB0004626 (Tetrahydrogestrinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra