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

• ChemBase编号: 5024
• 分子式: C19H24O2
• 平均质量: 284.39266
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: androsta-1,4-diene-3,17-dione; boldione
• 别名: 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

登记号

• CAS号: 897-06-3
• EC号: 212-977-2
• MDL号: MFCD00003614
• PubChem SID: 160968456; 99443844; 24891245
• PubChem CID: 13472
• Chemspider ID: 12893
• 维基百科标题: Boldione

理论计算性质

JChem

• Acid pKa: 18.826239
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.9267745
• LogD (pH = 7.4): 3.9267745
• Log P: 3.9267745
• 摩尔折射率: 84.7008 cm^3
• 极化性: 32.47242 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.78
• LOG S: -4.23
• 溶解度: 1.69e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 137-140°C

安全信息

• 保存条件: Refrigerator
• RTECS编号: BV7988000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 相关基因信息: human ... CYP19A1(1588)

详细说明

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.

参考文献

• 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)