(10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one

• ChemBase ID: 4525
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C1CC2=C3C=C[C@]4([C@H]([C@@H]3CCC2=CC1=O)CC[C@]4(CC)O)CC
• Canonical SMILES: CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@]2(O)CC
• InChI: 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
• InChIKey: OXHNQTSIKGHVBH-ANULTFPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one; (10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6,16-trien-5-one
• IUPAC Traditional name: tetrahydrogestrinone
• Synonyms: 17-HYDROXY-18A-HOMO-19-NOR-17ALPHA-PREGNA-4,9,11-TRIEN-3-ONE; (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-3-one; THG; Tetrahydrogestrinone 90%

Database IDs

• CAS Number: 618903-56-3
• PubChem SID: 99443341; 160967957
• PubChem CID: 6857686

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.90325
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.5018842
• LogD (pH = 7.4): 3.501885
• Log P: 3.501885
• Molar Refractivity: 95.4179 cm^3
• Polarizability: 36.470516 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.95
• LOG S: -4.2
• Solubility (Water): 1.99e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 60-62°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

DrugBank - DB06870

Drug information: experimental

Toronto Research Chemicals - T293600

Androgen and progestin; hydrogenation product of Gestrinone. (anabolic steroid).

REFERENCES

• Labrie, F., et al.: Steroids, 62, 148 (1997)
• Death, A.K., et al.: J. Clin. Endocrinol. Metab., 89, 2498 (1997)
• Labrie, F., et al.: J. Endocrinol., 187, 169 (1997)
• Wang, Y., et al.: Lancet, 365, 671 (1997)