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Showing NP-Card for Tetrahydrogestrinone (NP0334731)

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Record Information
Version2.0
Created at2024-09-10 19:43:09 UTC
Updated at2024-09-10 19:43:09 UTC
NP-MRD IDNP0334731
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetrahydrogestrinone
DescriptionTetrahydrogestrinone, also known as THG, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. In 2003, whistleblower Trevor Graham passed a spent syringe containing a small amount of the drug to the United States Anti-Doping Agency. THG, possessing a high affinity, establishes more van der Waals contacts with the receptor than with many other steroids. Tetrahydrogestrinone is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a modification of gestrinone (17α-ethynyl-18-methyl-19-nor-δ9,11-testosterone) in which the ethynyl group has been hydrogenated into an ethyl group, thereby converting the steroid from a norethisterone (17α-ethynyl-19-nortestosterone) derivative with weak AR activity into a norethandrolone (17α-ethyl-19-nortestosterone) derivative with powerful AR activity. Here it changes the expression of a variety of genes, turning on several anabolic and androgenic functions. Unlike most other anabolic steroids, THG also binds with high affinity to the glucocorticoid receptor, and while this effect may cause additional weight loss, it is also likely to cause additional side effects such as immunosuppression that are not seen with most other steroids. Tetrahydrogestrinone was first documented in 2004 (PMID: 15292520). It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Marion Jones and Dwain Chambers (PMID: 15934041).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334731 (Tetrahydrogestrinone)


  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
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   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
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   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
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 18 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END
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3D MOL for NP0334731 (Tetrahydrogestrinone)

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3D SDF for NP0334731 (Tetrahydrogestrinone)

  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
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  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>
NP0334731

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0334731 (Tetrahydrogestrinone)
Download
PDB for NP0334731 (Tetrahydrogestrinone)
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

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3D PDB for NP0334731 (Tetrahydrogestrinone)
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SMILES for NP0334731 (Tetrahydrogestrinone)
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]
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INCHI for NP0334731 (Tetrahydrogestrinone)
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
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Synonyms
ValueSource
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-3-oneHMDB
THGHMDB
17-HYDROXY-18a-homo-19-nor-17a-pregna-4,9,11-trien-3-oneHMDB
17-HYDROXY-18a-homo-19-nor-17α-pregna-4,9,11-trien-3-oneHMDB
TetrahydrogestrinoneMeSH
Chemical FormulaC21H28O2
Average Mass312.4458 Da
Monoisotopic Mass312.20893 Da
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 Nametetrahydrogestrinone
CAS Registry NumberNot Available
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 KeyOXHNQTSIKGHVBH-ANULTFPQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassEstrane steroids  
Direct ParentEstrogens 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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.95ALOGPS
logP3.5ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.9ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.42 m³·mol⁻¹ChemAxon
Polarizability37.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004626  
DrugBank IDDB06870  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023385  
KNApSAcK IDNot Available
Chemspider ID5257020  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrogestrinone  
METLIN IDNot Available
PubChem Compound6857686  
PDB ID17H  
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1002/jms.873. [PubMed:15934041  ] 
  2. Handelsman DJ: Designer androgens in sport: when too much is never enough. Sci STKE. 2004 Jul 27;2004(244):pe41. doi: 10.1126/stke.2442004pe41. [PubMed:15292520  ]