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

• ChemBase编号: 106017
• 分子式: C21H34O2
• 平均质量: 318.49346
• 单一同位素质量: 318.25588033
• SMILES: O=C(C)[C@@H]1[C@]2(CC[C@H]3[C@H]([C@@H]2CC1)CC[C@H]1C[C@H](O)CC[C@]31C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: AURFZBICLPNKBZ-SYBPFIFISA-N

名称和登记号

名称

• IUPAC标准名: 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethan-1-one; 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
• IUPAC传统名: 3a-hydroxy-5a-pregnan-20-one; 3α-hydroxy-5α-pregnan-20-one
• 别名: 3α-Hydroxy-5α-pregnan-20-one; 3α-OH-DHP; Allopregnan-3α-ol-20-one; Allopregnanolone; 5α-Pregnan-3α-ol-20-one; Allopregnan-3α-ol-20-one; 3α-Hydroxy-5α-20-one; ALLOPREGNANOLONE; (+)-3α-Hydroxy-5α-pregnan-20-one; (3α,5α)-3-Hydroxypregnan-20-one; 3α,5α-THP; 3α,5α-Tetrahydroprogesterone; 3α-Hydroxy-5α-dihydroprogesterone; 3α-Hydroxy-5α-pregnane-20-one; 5α-Pregnan-3α-ol-20-one; 5α-Pregnane-3α-ol-20-one; Allotetrahydroprogesterone; (3α)-Allopregnanolone

登记号

• CAS号: 516-54-1
• MDL号: MFCD00003677
• Beilstein号: 3211363
• PubChem SID: 24278659; 162089001
• PubChem CID: 92786

理论计算性质

• Acid pKa: 18.296396
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.986938
• LogD (pH = 7.4): 3.986938
• Log P: 3.986938
• 摩尔折射率: 92.9067 cm^3
• 极化性: 37.18642 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

分子性质

理化性质

• 溶解度: chloroform: soluble20 mg/mL, clear, colorless; DMSO: soluble5 mg/mL; methanol: soluble
• 外观: white solid

安全信息

• 保存条件: Room Temperature (15-30°C), Protect from light, Avoid excess heat
• RTECS编号: TU4383000
• 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

• 相关基因信息: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)mouse ... Gabrg2(14406)rat ... Gabra1(29705), Gabra2(29706), Gabrg2(29709)

产品相关信息

• 纯度: ≥95%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C21H34O2

详细说明

MP Biomedicals - 02195886

Purity: >95%
A neurosteroid with potent ligand properties against GABA Type A receptor complexes in mammalian CNS potentiating the GABA receptor-mediated chloride uptake in synaptoneurosomes.

Sigma Aldrich - P8887

Biochem/physiol Actions
Positive allosteric modulator of GABAA chloride channel.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P8887.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A547100

(3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain.

参考文献

• Puja, G. et al.: Neuron, 4, 759 (1990)
• Belelli, D. et ael. Neurosteroid, 6, 565 (1990)
• Viapiano, M. et al.: Neurochem. Res., 23, 155 (1990)