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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 550
実験および物理化学的性質
LogP
4.22
4.22
Collision Cross Section
172.95 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
177.25 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
174 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
214.8 Ų [M+Na]+
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)
- 闪点
- 9 ℃ · 9℃
- 貯蔵温度
- Refrigerator
- 溶解性
- 10 mg/mL · エタノール:可溶 10mg/mL 無色透明~微黄色
- 外見
- 粉
- 酸解離定数(Pka)
- 15 · 15.00±0.70(Predicted)
- 色
- ホワイトからオフホワイト
- 水溶解度
- 41 mg/L · 41mg/L(室温)
- Merck
- 7733 · 7733
- BRN
- 2059026 · 2059026
- 主な用途
- 臨床検査臨床検査
- 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
- SMILES
- O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C
- LogP
- 4.4 at · 4.4 at 20℃
- CAS データベース
- 145 · 145-13-1(CAS DataBase Reference)
- NISTの化学物質情報
- Pregnenolone(145-13-1)
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
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
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
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
Metabolism/Metabolites
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.
応用分野
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.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
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
関連ノート
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