プレグネノロン

Pregnenolone

HCID 8955CAS 145-13-1

基本情報

標準SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-N
分子式
C21H32O2
平均分子量
316.5 g/mol
単同位体質量
316.24023026

概要

Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-oxo steroid and a C21-steroid. It derives from a hydride of a pregnane.

名称と識別子

優先名称
Pregnenolone
IUPAC
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
現地名
プレグネノロン
英語名
Pregnenolone
分子式
C21H32O2
分子量
316.48

名称と別名

pregnenolone145-13-13beta-Hydroxypregn-5-en-20-oneArthenoloneRegnosoneSkinostelonEneloneNatoloneBina-Skin5-Pregnen-3beta-ol-20-onedelta5-Pregnenolone5-Pregnen-3-beta-ol-20-one
名称をさらに表示
プレグネノロン3β-ヒドロキシプレグン-5-エン-20-オンプレノロン3β-ヒドロキシ-5-プレグネン-20-オン3β-ヒドロキシプレグナ-5-エン-20-オン20-オキソプレグナ5-エン-3β-オール20-オキソプレグナ-5-エン-3β-オールΔ5-プレグネン-3β-オール-20-オン5-プレグネン-3Β-オール-20-オンプレグネノロン (JAN)1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-ヒドロキシ-9a,11a-ジメチル-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-1-イル]エタン-1-オン1-[(1S,3aS,3bS,9aR,9bS,11aS)-7-ヒドロキシ-9a,11a-ジメチル-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-1-イル]エタン-1-オン3-ヒドロキシ-プレグナ-5-エン-20-オン3-ヒドロキシプレグナ-5-エン-20-オン3β-Hydroxypregn-5-en-20-onePregneloneprenenolone5-pregnen-3B-ol-20-one5-pregnen-3β-ol-20-oneDELTA5-PREGNEN-3BETA-OL-20-ONE5-PregZK-5553-20-oneprenolon
PregnenolonaPregnenolonumDTXSID10365413-beta-Hydroxypregn-5-en-20-onePregn-5-en-20-one, 3-hydroxy-, (3beta)-73R90F7MQ81-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanoneDTXCID9016541

データベース識別子

CAS
145-13-1
PubChem CID
8955
DTXSID
DTXSID1036541
ChEMBL
CHEMBL253363
ChEBI
CHEBI:16581
UNII
73R90F7MQ8
EC Number
205-647-4
Nikkaji
J11.381F

物性

構造計算による物性

XLogP
4.2
極性表面積
37.3 Ų
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

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
LogP · 2 件

4.22

4.22

Solubility0.00706 mg/mL at 37 °C
Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点
188 · 188-190 °C
比旋光度
28.5 · 28.5 º (c=1, EtOH)
沸点
395.89 °C · 395.89°C (rough estimate)
比重(密度)
1.0382 · 1.0382 (rough estimate)
蒸気圧
0 · 0-0Pa at 20-25℃
屈折率
1.5344 · 1.5344 (estimate)

化学的性質

化学的特性white to off-white powder

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.

Warning

H302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationStatus: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422
Hazard Classes and CategoriesAcute Tox. 4 (87%)

安全データ

wgk
3
rtecs
TU5560700
ridadr
UN 1648 3 / PGII
hs_code
29372900
safety_code
22-24/25
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, Pregn-5-en-20-on-3b-yl sulfurate, and 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone.

Tissue LocationsAdrenal Cortex
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
応用分野 · 6 件

解説(3β)-3-hydroxypregn-5-en-20-one.C21H32O2(316.48).プレグネノロンは,コレステロール,ジオスゲニン,スチグマステロールなどから合成される.無色の針状結晶.融点190 ℃.[α]D+28°(エタノール).クロロホルムに可溶,エタノールに微溶,ベンゼン,石油エーテルに難溶.副じん皮質ホルモン,プロゲステロンなどの合成で重要な中間体である.森北出版「化学辞典(第2版)

用途プレグネノロン (pregnenolone) は、プロゲステロン、コルチコイド、アンドロゲン、およびエストロゲンのステロイド生成にかかわるプロホルモンである。

用途プレグネノロンは体内であらゆるホルモンに変換されるプロホルモンである。

説明Pregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.

使用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 an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A

一般的な説明Pregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

補足説明

定義ChEBI: A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20.

関連反応

11 件

関連ノート

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