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

• ChemBase编号: 2503
• 分子式: C21H32O2
• 平均质量: 316.47758
• 单一同位素质量: 316.24023026
• SMILES: C1C[C@H](O)CC2=CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
• InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: ORNBQBCIOKFOEO-QGVNFLHTSA-N

名称和登记号

名称

• IUPAC标准名: 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethan-1-one; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
• IUPAC传统名: pregnenolone
• 别名: 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone; 3-Hydroxypregn-5-en-20-one; Pregnenolone; Pregnenolone; 3β-Hydroxy-5-pregnen-20-one; Pregnenolone; 5-Pregnen-3β-ol-20-one; (3β)-3-Hydroxy-pregn-5-en-20-one; (3β)-3-Hydroxypregn-5-en-20-one; 5-Pregnenolone; Arthenolone; Bina-Skin; Enelone; NSC 1616; Pregnolon; Prenolon; Regnosone; Skinostelon

登记号

• CAS号: 145-13-1
• EC号: 205-647-4
• MDL号: MFCD00003628
• Beilstein号: 2059026
• PubChem SID: 160965953; 24899008; 46506718; 24887880
• PubChem CID: 8955

理论计算性质

JChem

• Acid pKa: 18.20429
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.5813584
• LogD (pH = 7.4): 3.5813584
• Log P: 3.5813584
• 摩尔折射率: 93.7567 cm^3
• 极化性: 36.94731 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.06
• LOG S: -4.37
• 溶解度: 1.36e-02 g/l

分子性质

理化性质

• 溶解度: Chlorform; Ethanol
• 外观: Cryst.; White Solid
• 熔点: 174-177°C; 188-190 °C
• 比旋光度: [α]20/D +27±1°, c = 1% in ethanol

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: TU5560700
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Estrogen receptor
• 相关基因信息: human ... SERPINA6(866)rat ... Ar(24208)

产品相关信息

• 纯度: ≥98%
• 级别: purum
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C21H32O2

详细说明

DrugBank - DB02789

• Drug Groups: experimental
• Description: A 21-carbon steroid, derived from CHOLESTEROL and found in steroid hormone-producing tissues. Pregnenolone is the precursor to GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS. [PubChem]

Selleck Chemicals - S1914

Biological Activity:

Sigma Aldrich - P9129

Biochem/physiol Actions
One of a small number of "neurosteroids," steroids synthesized in the brain rather than peripheral sources. Decreased levels of these neurosteroids has been implicated in rodent cognitive decline with age, but studies in humans have been contradictory.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P9129.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 81630

Biochem/physiol Actions
One of a small number of "neurosteroids," steroids synthesized in the brain rather than peripheral sources. Decreased levels of these neurosteroids has been implicated in rodent cognitive decline with age, but studies in humans have been contradictory.1

Toronto Research Chemicals - P712200

Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA antagonist and increases neurogenesis in the hippocampus.

参考文献

• Geick, A., et al.: J. Biol. Chem., 276, 14581 (1976)
• Johnson, D., et al.: Toxicol. Sci., 66, 16 (1976)
• Abe, C., et al.: Lipids, 42, 637 (1976)
• Bjondahl, K., et al.: Med. Biol., 54, 454 (1976)