(2S,4E,7S,14S,15S)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 119808
• Molecular Formular: C21H32O3
• Molecular Mass: 332.47698
• Monoisotopic Mass: 332.23514488
• SMILES: [C@@]12(C3C(C4[C@@]([C@](CC4)(O)C)(CC3)C)CC[C@H]2CC(=O)/C(=C/O)/C1)C
• Canonical SMILES: O/C=C/1\C[C@@]2(C)[C@H](CC1=O)CCC1C2CC[C@]2(C1CC[C@]2(C)O)C
• InChI: InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12+/t14-,15?,16?,17?,19-,20-,21-/m0/s1
• InChIKey: ICMWWNHDUZJFDW-XROWNTGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4E,7S,14S,15S)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: (2S,4E,7S,14S,15S)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• Synonyms: (5S,10S,13S,17S,E)-17-hydroxy-2-(hydroxymethylene)-10,13,17-trimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; Adroyd; Anapolon; Anadrol; Anasterone; Synasteron; Oxymetholone

Database IDs

• CAS Number: 434-07-1
• PubChem SID: 162107925
• PubChem CID: 17571563

CALCULATED PROPERTIES

• Acid pKa: 8.519246
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.552314
• LogD (pH = 7.4): 3.5209312
• Log P: 3.5527294
• Molar Refractivity: 94.5969 cm^3
• Polarizability: 37.560345 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Anabolic steroid; Protein synthesis stimulator

Product Information

• Application(s): Active in treating HIV wasting syndrome

REFERENCES

• Ringold, H.J. et al., J.A.C.S., 1959, 81, 427, (synth)
• Clinton, R.O. et al., J.A.C.S., 1959, 81, 1513, (synth, uv)
• Ger. Pat., 1961, 1 070 632; CA, 55, 8480, (synth)
• Junkmann, K. et al., Arzneim.-Forsch., 1962, 12, 214, (pharmacol)
• Clinton, R.O. et al., J.O.C., 1962, 27, 2800, (synth, uv)
• Volovel'skii, L.N. et al., Zh. Obshch. Khim., 1963, 33, 676, (synth, uv)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6370, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1193
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PAN100