7-オキソデヒドロエピアンドロステロン

7-Keto-dehydroepiandrosterone

HCID 193313CAS 566-19-8

基本情報

標準SMILES: C[C@]12CC[C@H](O)CC1=CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey: KPRGOTLNGIBVFL-GINZOMEDSA-N
分子式: C19H26O3
平均分子量: 302.4 g/mol
単同位体質量: 302.18819469

概要

7-ketodehydroepiandrosterone is a 3beta-hydroxy-5-steroid that is dehydroepiandrosterone carrying an additional oxo group at position 7. It has a role as a nutraceutical, a prohormone and a human blood serum metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 17-oxo steroid, a 7-oxo steroid and an androstanoid. It is functionally related to a dehydroepiandrosterone.

名称と識別子

優先名称: 7-Keto-dehydroepiandrosterone
IUPAC: (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
現地名: 7-オキソデヒドロエピアンドロステロン
英語名: 7-Keto-dehydroepiandrosterone
分子式: C19H26O3
分子量: 302.41

名称と別名

7-Keto-dehydroepiandrosterone7-Keto-DHEA7-Oxodehydroepiandrosterone7-oxo-dehydroepiandrosterone2334LJD2E9RefChem:1065273 beta-hydroxyandrost-5-ene-7,17-dione566-19-87-Ketodehydroepiandrosterone7-Oxo-DHEA7-Keto Dehydro Epiandrosterone3beta-Hydroxyandrost-5-ene-7,17-dione

名称をさらに表示

7-オキソ-デヒドロエピアンドロステロン7-オキソ-DHEA(3aS,3bR,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-1,4-ジオン7-オキソデヒドロエピアンドロステロン3β-ヒドロキシ-5-アンドロステン-7,17-ジオン3β-ヒドロキシアンドロスタ-5-エン-7,17-ジオン7-ケトデヒドロエピアンドロステロン7-Ketoprasterone7-KETO DHEA, HPLC 98%ABiraterone Impurity I7-Keto DHEA (Standard)7-keto DHEA(7-Oxo DHEA)7-Keto-dehydroepiandrosteKetodehydroepiandrosterone7-keto DHEA Acetate Powder

MFCD00198500(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dioneAndrost-5-ene-7,17-dione, 3-hydroxy-, (3b)-7-keto DHEA7-KetoDHEA, 7-keto-3-Hydroxy-10,13-dimethyl-3,4,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17(2H,8H)-dione7-Keto Dehydro Epiandrosterone (1.0mg/ml in Methanol)

データベース識別子

CAS: 566-19-8
PubChem CID: 193313
DTXSID: DTXSID801024029
ChEMBL: CHEMBL1875999
ChEBI: CHEBI:183808
UNII: 2334LJD2E9
EC Number: 111-754-6
Nikkaji: J672.472H

物性

構造計算による物性

XLogP: 2
極性表面積: 54.4 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 0
重原子数: 22
形式電荷: 0
複雑度: 577

物理化学的性質

融点: 245 · 245-248 °C
沸点: 477.1 · 477.1±45.0 °C(Predicted)
比重(密度): 1.19 · 1.19±0.1 g/cm3(Predicted)
溶解性: 25 mg/ml; · DMF: 25 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 15 mg/ml; Ethanol: 10 mg/ml
外見: A crystalline solid
酸解離定数(Pka): 14.67 · 14.67±0.60(Predicted)
InChI: InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/s3
InChIKey: KPRGOTLNGIBVFL-YQJRJXGQNA-N
SMILES: C[C@]12CC[C@H](O)CC1=CC(=O)[C@@]1([H])[C@]3([H])CCC(=O)[C@@]3(C)CC[C@]21[H] |&1:1,4,11,13,19,23,r|
CAS データベース: 566 · 566-19-8(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

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

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

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesCarc. 2 (100%)

化学と産業

応用分野 · 1 件

説明7-Ketodehydroepiandrosterone (7-Keto-dehydroepiandrosterone; 7-keto-DHEA), chemically known under 3-acetyl-7-oxo-dehydroepiandrosterone, is a naturally occurring metabolite of the steroid hormone dehydroepiandrosterone (DHEA) and is marketed as such an anti-obesity dietary supplement. The synthesis of 7-keto-DHEA begins with an irreversible hydroxylation of DHEA in the position C7 by cytochrome P450 7B1 (CYP7B1) under the formation of 7 α-hydroxy-dehydroepiandrosterone (7 α-OH-DHEA). β-hydroxysteroid dehydrogenase type 1 (11 β-HSD 1) then catalyzes the interconversion of 7 α-OH-DHEA and 7 β-hydroxy-dehydroepiandrosterone (7 β-OH-DHEA) through a 7-keto-DHEA intermediary. DHEA is a "parent hormone" produced by glands near the kidneys. However, unlike DHEA, 7-keto-DHEA is not converted to steroid hormones such as androgen and estrogen. Taking 7-keto-DHEA by mouth or applying it to the skin does not increase the level of steroid hormones in the blood. People take 7-keto-DHEA for obesity, muscle strength, anxiety, depression, and other conditions. However, there is no good scientific evidence to support these uses[1].

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