3α-ヒドロキシ-5β-プレグナ-20-オン

Pregnanolone

HCID 31402CAS 128-20-1

基本情報

標準SMILES: CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: AURFZBICLPNKBZ-YZRLXODZSA-N
分子式: C21H34O2
平均分子量: 318.5 g/mol
単同位体質量: 318.25588033

概要

3alpha-hydroxy-5beta-pregnan-20-one is the 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one. It has a role as a sedative, an intravenous anaesthetic and a human metabolite. It is a 3alpha-hydroxy steroid and a 3-hydroxy-5beta-pregnan-20-one.

名称と識別子

優先名称: Pregnanolone
IUPAC: 1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
現地名: 3α-ヒドロキシ-5β-プレグナ-20-オン
英語名: Eltanolone
分子式: C21H34O2
分子量: 318.49

名称と別名

PregnanoloneELTANOLONE128-20-13alpha-Hydroxy-5beta-pregnan-20-oneEltanolonaPregnan-3alpha-ol-20-oneEltanolonumDTXSID1046342Pregnan-20-one, 3-hydroxy-, (3alpha,5beta)-(3alpha,5beta)-3-hydroxypregnan-20-oneBXO86P3XXWKabi 2213

名称をさらに表示

エルタノロンプレグナノロンII3α-ヒドロキシ-5β-プレグナ-20-オン5β-プレグナン-3α-オール-20-オン3α-ヒドロキシ-5β-プレグナン-20-オンプレグナノロン20-オキソ-5β-プレグナン-3α-オール3α,5β-テトラヒドロプロゲステロンプレグナン-3α-オール-20-オン5β-Pregnan-3α-ol-20-oneSKF 6455Kabi2213NSC 82867Pregnanolone IIEPIPREGNANOLONE

Kabi-2213SKF-6455NSC-82867Allopregnan-3 beta-ol-20-one1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone3 Hydroxypregnan 20 onePregnan 3alpha ol 20 one3 alpha, 5 beta-Tetrahydroprogesterone

データベース識別子

CAS: 128-20-1
PubChem CID: 31402
DTXSID: DTXSID1046342
ChEMBL: CHEMBL210952
ChEBI: CHEBI:1712
UNII: BXO86P3XXW
EC Number: 634-188-6
Nikkaji: J6.567F

物性

構造計算による物性

XLogP: 4.9
極性表面積: 37.3 Å²
水素結合供与体数: 1
水素結合受容体数: 2
回転可能結合数: 1
重原子数: 23
形式電荷: 0
複雑度: 500

実験および物理化学的性質

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点: 149 °C · 149°C
比旋光度: 23 · D23 +59.6° (c = 0.3 in chloroform); D26 +108.5 ±1° (c = 9.23 mg/1.23 ml abs ethanol)
沸点: 397.64 °C · 397.64°C (rough estimate)
比重(密度): 1.0234 · 1.0234 (rough estimate)
屈折率: 1.5344 · 1.5344 (estimate)
貯蔵温度: Store at RT
溶解性: クロロホルム（微量）、エタノール（微量）、メタノール（微量）
酸解離定数(Pka): 15.12 · 15.12±0.70(Predicted)
外見: 個体
色: ホワイトからオフホワイト
由来生物: synthetic (organic)
水溶解度: 8 mg/L · 8mg/L(室温)
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
InChIKey: AURFZBICLPNKBZ-UHFFFAOYSA-N
SMILES: [H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2
NISTの化学物質情報: 3 Alpha-hydroxy-5beta-pregnan-20-one · 3Alpha-hydroxy-5beta-pregnan-20-one(128-20-1)

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesCarc. 2 (100%)

安全データ

wgk: 3
rtecs: TU4384000
毒性: LD50 in mice, rats (mg/kg): 66 ± 10, 27.5 ± 2.4 i.v. (Gyermek)
risk_code: 40
hazard_code: Xn
safety_code: 22-36
Hazard Classifications: Carc. 2
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological Classification · 1 件

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.