(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,14-dione

• ChemBase ID: 5024
• Molecular Formular: C19H24O2
• Molecular Mass: 284.39266
• Monoisotopic Mass: 284.17763001
• SMILES: C1=CC(=O)C=C2[C@@]1(C)[C@H]1CC[C@]3([C@@H](CCC3=O)[C@@H]1CC2)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
• InChIKey: LUJVUUWNAPIQQI-QAGGRKNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione; (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione
• IUPAC Traditional name: androsta-1,4-diene-3,17-dione; boldione
• Synonyms: Androsta-1,4-diene-3,17-dione; Δ1,4-Androstadiene-3,17-dione; NSC 49080; (8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione; ANDROSTA-1,4-DIENE-3,17-DIONE; 1,4-ANDROSTADIEN-3,17-DIENE; 1-Dehydroandrostenedione; Androstadienedione; 1,4-Androstadiene-3,17-dione; 1,4-Androstadiene-3,17-dione; Androsta-1,4-diene-dione, Androsta-1,4-diene,3,17-dione; Boldione

Database IDs

• CAS Number: 897-06-3
• EC Number: 212-977-2
• MDL Number: MFCD00003614
• PubChem SID: 160968456; 99443844; 24891245
• PubChem CID: 13472
• Chemspider ID: 12893
• Wikipedia Title: Boldione

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.826239
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.9267745
• LogD (pH = 7.4): 3.9267745
• Log P: 3.9267745
• Molar Refractivity: 84.7008 cm^3
• Polarizability: 32.47242 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.78
• LOG S: -4.23
• Solubility (Water): 1.69e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 137-140°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: BV7988000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: human ... CYP19A1(1588)

DETAILS

MP Biomedicals - 05203976

MP Biomedicals Rare Chemical collection

DrugBank - DB07373

Drug information: experimental

Sigma Aldrich - A7505

Application
1,4-Androstadiene-3,17-dione is a prohormone that converts to an active steroid through the 17bHSD enzyme. 1,4-Androstadiene-3,17-dione is a metabolite of progesterone.

Toronto Research Chemicals - B675200

Boldenone related steroid; anabolic androgenic steroid.

REFERENCES

• Watanabe, K., et al.: J. Appl. Bacteriol., 62, 1511 (1987)
• Barthakur, S., et al.: J. Basic Microbiol., 36, 383 (1987)
• Grinenko, G., et al.: Pharmaceut. Chem. J., 36, 510 (1987)
• Bhat, S., et al.: J. Biol. Chem., 280, 33015 (1987)