(1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 1241
• Molecular Formular: C18H24O2
• Molecular Mass: 272.38196
• Monoisotopic Mass: 272.17763001
• SMILES: [C@]12(C(=O)CC[C@H]1[C@H]1[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC1)C
• Canonical SMILES: O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1
• InChIKey: JRIZOGLBRPZBLQ-QXUSFIETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione; (1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: 19-norandrostenedione
• Brand Name: Bolandione; 19-N-Andro; Proven Pure 19-Norandrostenedione
• Synonyms: delta4-Estrene-3,17-dione; 19-norandrostenedione; Estr-4-ene-3,17-dione; 9-Nor-4-androstenedione; 19-Norandrost-4-ene-3,17-dione; 3,17-Dioxo-19-norandrost-4-ene; NSC 12164; d-19-Norandrost-4-ene-3,17-dione; (+)-19-Norandrost-4-ene-3,17-dione

Database IDs

• CAS Number: 734-32-7
• PubChem SID: 46505377; 160964701
• PubChem CID: 92834
• Chemspider ID: 83803
• DrugBank ID: DB01434
• Wikipedia Title: 19-Norandrostenedione

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.19337
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.6289039
• LogD (pH = 7.4): 3.6289039
• Log P: 3.6289039
• Molar Refractivity: 79.1324 cm^3
• Polarizability: 30.86945 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -3.78
• Solubility (Water): 4.54e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 169-172°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Schedule III (US)

DETAILS

DrugBank - DB01434

• Drug Groups: experimental; nutraceutical
• Description: 19-Norandrostenedione refers to two steroid isomers that are marketed as dietary supplements and mainly used by body builders.
• Indication: The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.
• Affected Organisms: Humans and other mammals
• Biotransformation: Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.
• Absorption: Absorption appears variable, but some absorption does occur
• External Links: PDRhealth

Toronto Research Chemicals - N661000

Norethindrone intermediate.

REFERENCES

• Carlin, J., et al.: Drug Metab. Dispos., 20, 148 (1982)
• Hoffmann, R., et al.: Clin. Exp. Dermatol., 27, 373 (1982)
• Tarter, T., et al.: Curr. Pharm. Des., 2, 775(1982)