基本情報
- CAS
81-23-2- 標準SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(=O)C[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC(=O)[C@]12C- InChIKey
OHXPGWPVLFPUSM-KLRNGDHRSA-N- 分子式
- C24H34O5
- 平均分子量
- 402.5 g/mol
- 単同位体質量
- 402.24062418
概要
3,7,12-trioxo-5beta-cholanic acid is an oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton. It has a role as a gastrointestinal drug. It is a 3-oxo-5beta-steroid, an oxo-5beta-cholanic acid, a 7-oxo steroid and a 12-oxo steroid. It is a conjugate acid of a 3,7,12-trioxo-5beta-cholan-24-oate.
名称と識別子
- 優先名称
- Dehydrocholic Acid
- IUPAC
- (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
- 現地名
- デヒドロコール酸
- 英語名
- Dehydrocholic acid
- 分子式
- C24H34O5
- 分子量
- 402.53
名称と別名
dehydrocholic acid81-23-2DecholinDilabilProcholonKetocholanic acidTriketocholanic acid3,7,12-Trioxocholanic acid3,7,12-Triketocholanic acid3,7,12-Trioxo-5beta-cholan-24-oic acid3,7,12-Triketo-5beta-cholanoic acid3,7,12-Trioxo-5beta-cholanic acid
名称をさらに表示
デヒドロコール酸ビロスタートジラビルデコリンオキシコリンデヒコールコラン-DHコラゴンデイドロコリコビタビルドレン3,7,12-トリオキソ-5β-コラン-24-酸ジドロコロアコレン3,7,12-トリオキソ-5β-コラン酸3,7,12-トリケトコール酸3,7,12-トリケトコラン酸エレビレフェラクリノス3,7,12-トリケト-5β-コラン酸3,7,12-トリオキソ?5Β?コラン酸DHCdehydrocholicAcolenAtrocholinDehydrocholate3,7,12-trioxo-5β-cholanic acid
物性
構造計算による物性
- XLogP
- 2.6
- 極性表面積
- 88.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 4
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 756
実験および物理化学的性質
Chemical ClassesBile Acids -> Canonical Bile Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
SolubilityInsoluble
Melting Point237-240
Collision Cross Section
194.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
192.1 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 238 · 238-240 °C
- 比旋光度
- 29 · 29 º (c=2, dioxane)
- 沸点
- 444.65 °C · 444.65°C (rough estimate)
- 比重(密度)
- 1.0687 · 1.0687 (rough estimate)
- 蒸気圧
- 0.013 Pa · 0.013Pa at 20℃
- 屈折率
- 30.5 ° · 30.5 ° (C=2, Dioxane)
- 貯蔵温度
- Sealed in dry,Room Temperature
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。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Cholan-24-oic acid, 3,7,12-trioxo-, (5.beta.)-
REACH registered substance: Dehydrocholic acid (EC: 201-335-7)
Cholan-24-oic acid, 3,7,12-trioxo-, (5.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- FZ2300000
- hs_code
- 2918300000
- 化審法
- (9)-835
- safety_code
- 24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Protein BindingNo pharmacokinetic data available.
Pharmacodynamics
Following infusion of dehydrocholic acid (DHCA) in rats, the secretions of all the endogenous biliary bile acids were decreased within 30-60 minutes of infusion. Phospholipid secretion as well as cholesterol levels were also declined. The bile flow was increased after administration of dehydrocholic acid.
Mechanism of Action
It is proposed that dehydrocholic acid induces choleresis, which is associated with biliary lipid secretion and reduced secretion of endogenous and/or exogenous biliary components. Dehydrocholic acid may decrease bile phospholipid secretion due to a lack of micelle formation by dehydrocholic acid-produced bile. A study suggests that due to enhanced permeability of tight junctions in the canalicular membranes, dehydrocholic acid facilitates direct exchange between bile and plasma.
Biological Half-LifeNo pharmacokinetic data available.
Metabolism/Metabolites
The major site of metabolism is proposed to be the liver. The major metabolite accounting for 70% of total detectable metabolites is dihydroxymonoketo bile acid (3α,7α-dihydroxy-12-keto-5β-cholanoic acid). About 20% of metabolites is monohydroxydiketoacid (3α-hydroxy-7,12-keto-5β-cholanoic acid) and about 10% is cholic acid.
MeSH Pharmacological ClassificationGastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Absorption, Distribution and Excretion
The duodenal experiment indicates that dehydrocholic acid is absorbed from the proximal small intestine.
Administered dehydrocholic acid is excreted rapidly in bile as glycine- and taurine-conjugated bile acids.
No pharmacokinetic data available.
No pharmacokinetic data available.
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