기본 정보
- CAS
81-23-2- 표준 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- 분자식
- C24H34O5
- 평균 분자량
- 402.5 g/mol
- 단동위원소 질량
- 402.24062418
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 영어명
- Dehydrocholic acid
- 분자식
- C24H34O5
- 분자량
- 402.53
이름 및 동의어
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
이름 더 보기
DHCdehydrocholicAcolenAtrocholinDehydrocholate3,7,12-trioxo-5β-cholanic acid5β-CHOLANIC acid-3, 7, 12-TRIONE(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidDee-CoBiochol
DTXSID2022888NSC-8796NH5000009ICholan-24-oic acid, 3,7,12-trioxo-, (5beta)-DTXCID402888(5beta)-3,7,12-trioxocholan-24-oic acidCHEBI:31459CholanHMB
데이터베이스 식별자
- CAS
81-23-2
물성
구조 계산 물성
- XLogP
- 2.6
- 극성 표면적
- 88.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 756
실험 및 물리화학적 성질
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]
물리화학적 성질
- 녹는점
- 238 · 238-240 °C
- 끓는 점
- 444.65 °C · 444.65°C (rough estimate)
- 밀도
- 1.0687 · 1.0687 (rough estimate)
- 증기압
- 0.013 Pa · 0.013Pa at 20℃
- 굴절률
- 30.5 ° · 30.5 ° (C=2, Dioxane)
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 10 mg/mL · 에탄올: 10mg/mL
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
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%)
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- FZ2300000
- HS 번호
- 2918300000
- safety_code
- 24/25
- 기존화학 물질
- KE-34726
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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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