Dehydrocholsure

Dehydrocholic Acid

HCID 6674

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Grundinformationen

CAS: 81-23-2
Standard-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
Summenformel: C24H34O5
Durchschnittliche Molmasse: 402,5 g/mol
Monoisotopische Masse: 402,24062418

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: 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
Lokaler Name: Dehydrocholsure
Englischer Name: Dehydrocholic acid
Summenformel: C24H34O5
Molmasse: 402.53

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

CAS: 81-23-2
PubChem CID: 6674
DTXSID: DTXSID2022888
ChEMBL: CHEMBL514446
ChEBI: CHEBI:31459
UNII: NH5000009I
EC Number: 201-335-7
Nikkaji: J3.858J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,6
Polarare Oberfläche (TPSA): 88,5 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 4
Schwere Atome: 29
Formalladung: 0
Komplexität: 756

Experimentelle und physikochemische Eigenschaften

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 · 2 Einträge

194.8 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]

192.1 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 238 · 238-240 °C
Siedepunkt: 444.65 °C · 444.65°C (rough estimate)
Dichte: 1.0687 · 1.0687 (rough estimate)
Dampfdruck: 0.013 Pa · 0.013Pa at 20℃
Brechungsindex: 30.5 ° · 30.5 ° (C=2, Dioxane)
storage temp.: Sealed in dry,Room Temperature
Löslichkeit: 10 mg/mL · ethanol: 10 mg/mL
pka: 5.12 · pKa 5.12(H2O t = 20 c > CMC) (Uncertain)
Aggregatzustand: Solid
Farbe: White to Off-White
Biologische Quelle: bovine bilesynthetic
Wasserlöslichkeit: 65 mg/L · 65mg/L(30 ºC)
Merck: 14 · 14,2868
BRN: 3226734 · 3226734
Major Application: pharmaceutical (small molecule)
InChIKey: OHXPGWPVLFPUSM-KLRNGDHRSA-N
SMILES: [H][C@@]12CC(=O)CC[C@]1(C)[C@@]3([H])CC(=O)[C@]4(C)[C@H](CC[C@@]4([H])[C@]3([H])C(=O)C2)[C@H](C)CCC(O)=O
LogP: 1.64 at · 1.64 at 22℃ and pH5.7
Oberflächenspannung: 56.9 mN/m · 56.9mN/m at 63mg/L and 20℃
CAS Datenbank: 81 · 81-23-2(CAS DataBase Reference)
NIST chemische Informationen: Dehydrocholic acid(81-23-2)
EPA chemische Informationen: -24 · Cholan-24-oic acid, 3,7,12-trioxo-, (5.beta.)- (81-23-2)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 3 Einträge

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%)

Sicherheitsdaten

wgk: 2
tsca: TSCA listed
hs_code: 2918300000
RTECS-Nr.: FZ2300000
safety_code: 24/25
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Protein BindingNo pharmacokinetic data available.

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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).

Verwendung und Herstellung

General Manufacturing InformationCholan-24-oic acid, 3,7,12-trioxo-, (5.beta.)-: ACTIVE

Anwendungen

VerwendenDehydrocholic Acid is a derivative of Cholic Acid (C432600). a choleretic produced by, and isolated from liver cells.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumacetat 2-[[(3α,5β,7α,12α)-3,7,12-Trihydroxy-24-oxocholan-24-yl]amino]ethansulfonsure Natriumdichromat Dihydrat Ethanol bilis extract N-(3-α,7-α,12-α-Trihydroxycholan-24-oyl)glycin Cholsure Natriumsulfit Tube990 (5R,7R,8R,9S,10S,13S,14S)-7-hydroxy-10,13-dimethyldodecahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,4H)-dione(WX116145)(3R,5S,7R,8R,9S,10S,13S,14S)-3,7-dihydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one(WX116146)4,6-Androstadien-3,17-dione

Nachgelagerte Produkte

3α,7α-Dihydroxy-12-oxo-5β-cholan-24-sure

Anbieter100 Anbieter

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上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]

Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

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HRID 1578586als Produktuspto-grants-1976_02

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