ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
  1. ホーム
  2. /化合物

3-beta-Hydroxyandrost-5-en-17-one 3-sulfate

HCID 20057076
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
129509-11-1
標準SMILES
C[C@]12CC[C@H](OS(=O)(=O)[O-])CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey
CZWCKYRVOZZJNM-USOAJAOKSA-M
分子式
C19H27O5S-
平均分子量
367.5 g/mol
単同位体質量
367.15792013

概要

Dehydroepiandrosterone sulfate(1-) is the conjugate base of 3beta-hydroxyandrost-5-en-17-one 3-sulfate arising from deprotonation of the sulfate OH group; major species at pH 7.3. It has a role as a human metabolite. It is a conjugate base of a dehydroepiandrosterone sulfate.

名称と識別子

優先名称
3-beta-Hydroxyandrost-5-en-17-one 3-sulfate
IUPAC
[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] sulfate

名称と別名

3-beta-hydroxyandrost-5-en-17-one 3-sulfateRefChem:1067400[3H]dehydroepiandrosterone sulfateCCG-20447317-oxoandrost-5-en-3beta-yl sulfate[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] sulfate[3H]dehydroepiandrosterone sulphate[3H]DHEASGTPL4528GTPL5577CHEBI:57905dehydroepiandrosterone sulfate(1-)
名称をさらに表示
DTXSID4012266073beta-sulfooxy-androst-5-en-17-oneNCGC00162137-02129509-11-1PD0483213beta-hydroxyandrost-5-en-17-one 3-sulfate anion3beta-hydroxyandrost-5-en-17-one 3-sulfate(1-)Q27077014

データベース識別子

CAS
129509-11-1
PubChem CID
20057076
DTXSID
DTXSID401226607
ChEBI
CHEBI:57905

物性

構造計算による物性

XLogP
2.8
極性表面積
91.9 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
1
重原子数
25
形式電荷
-1
複雑度
707

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全と保護具

Minimum Risk LevelDehydroepiandrosterone sulfate levels above 1890 micromol/L or 700-800 µg/dL are highly suggestive of adrenal dysfunction.

毒性情報

Health Effects · 1 件

Some researchers believe DHEAS supplements might actually raise the risk of breast cancer, prostate cancer, heart disease, diabetes and stroke. DHEAS may stimulate tumor growth in types of cancer that are sensitive to hormones, such as some types of breast, uterine, and prostate cancer. DHEAS may increase prostate swelling in men with benign prostatic hyperplasia (BPH), an enlarged prostate gland. High doses of DHEAS may cause aggressiveness, irritability, trouble sleeping, and the growth of body or facial hair on women. It also may stop menstruation and lower the levels of HDL ('good' cholesterol), which could raise the risk of heart disease. Other reported side effects include acne, heart rhythm problems, liver problems, hair loss (from the scalp), and oily skin. In women, DHEA may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency. DHEAS may interfere with the way the body processes certain agents using the liver's cytochrome P450 enzyme system. Chronically high levels of Dehydroepiandrosterone sulfate are associated with male pseudohermaphrodism with gynecomastia.

Exposure RoutesEndogenous, ingestion
Toxicity Summary · 1 件

Although it predominantly functions as an endogenous precursor to more potent androgens such as testosterone and dihydroxytestosterone, DHEA (which is produced from DHEAS) has been found to possess some degree of androgenic activity in its own right, acting as a low affinity (Ki = 1 μM), weak partial agonist of the androgen receptor. DHEA has also been found to bind to and activate the ERα and ERβ estrogen receptors with Ki values of 1.1 μM and 0.5 μM, respectively. When taken in sufficient quantities DHEAS can cause masculinizing effects. DHEAS is considered an androgenic steroid precursor because testosterone (its product) is an androgen or male hormone. In males and females, conversion of DHEAS to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. Testosterone plays a key role in the development of male reproductive tissues such as the testis and prostate as well as promoting secondary sexual characteristics such as increased muscle, bone mass, and the growth of body hair. High levels of testosterone can lead to masculinization in females or premature puberty in young boys. Chronically high levels in adults increase the incidence of heart attack, stroke and blood clots by lowering the level of HDL (good cholesterol). The development of breast tissue in males, a condition called gynecomastia (which is usually caused by high levels of circulating estradiol), arises because of increased conversion of testosterone to estradiol by the enzyme aromatase. Reduced sexual function and temporary infertility can also occur in males.

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Dehydroepiandrosterone sulfate (DHEAS) is the sulfate ester of DHEA. This conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestine. DHEA sulfate can also be back-converted to DHEA through the action of steroid sulfatase. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally ingested DHEA is converted to its sulfate when passing through intestines and liver. DHEAS levels show no diurnal variation. In males and females, conversion of DHEAS to DHEA and then to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase.

用途と製造

UsesInvestigated for use/treatment in asthma and burns and burn infections.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Signs and Symptoms · 1 件

In women, DHEAS may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).