(1S,2R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-3-en-5-one

• ChemBase编号: 1278
• 分子式: C19H28O2
• 平均质量: 288.42442
• 单一同位素质量: 288.20893014
• SMILES: O[C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)CC(=O)C=C4)C)CC2)CC1)C
• Canonical SMILES: O=C1C=C[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H28O2/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/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: OKJCFMUGMSVJBG-ABEVXSGRSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-5-one; (1S,2R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-one
• IUPAC传统名: 1-testosterone; delta1-dihydrotestosterone
• 别名: 1-Testosterone; 17beta-hydroxy-5alpha-androst-1-en-3-one; 1-testosterone; 1-Testo; 1-T; Delta1-dihydrotestosterone

登记号

• CAS号: 65-06-5
• PubChem SID: 46507716; 160964738
• PubChem CID: 236666; 579094
• CHEBI ID: 59714
• Chemspider ID: 206590
• DrugBank ID: DB01481
• 维基百科标题: 1-Testosterone

理论计算性质

JChem

• Acid pKa: 19.377705
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.409081
• LogD (pH = 7.4): 3.4090812
• Log P: 3.4090812
• 摩尔折射率: 84.6964 cm^3
• 极化性: 33.260063 Å^3
• 极化表面积: 37.3 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: 3.38
• LOG S: -4.35
• 溶解度: 1.28e-02 g/l

分子性质

药理学性质

• 代谢: Liver
• 法定药品分级: Schedule III (US)

详细说明

DrugBank - DB01481

• Drug Groups: illicit; experimental
• Description: Delta1-dihydrotestosterone is an anabolic steroid that differs from testosterone by having a 1,2-double bond instead of 4,5-double bond in its A ring. [Wikipedia]
• Pharmacology: Delta1-dihydrotestosterone binds to the androgen receptor, a nuclear receptor which binds the androgenic hormones testosterone and dihydrotestosterone. Once bound, the receptor/ligand complex localizes to the nucleus and acts as a DNA binding transcription factor, regulating gene expression. In animals, Delta1-dihydrotestosterone stimulates the growth of the prostate as well as the seminal vesicles.
• Affected Organisms: Humans and other mammals
• References: Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. [Pubmed]

参考文献

• Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. Pubmed