7-Ketolithocholic acid

HCID 444262

Basic information

CAS
4651-67-6
Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(=O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
DXOCDBGWDZAYRQ-AURDAFMXSA-N
Molecular formula
C24H38O4
Average molar mass
390.6 g/mol
Monoisotopic mass
390.27700969

Names & identifiers

Preferred name
7-Ketolithocholic acid
IUPAC
(4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
English name
3alpha-Hydroxy-7-oxo-5beta-cholanic Acid
Molecular formula
C24H38O4
Molecular weight
390.56

Names & synonyms

4651-67-67-Ketolithocholic acidNutriacholic acid3alpha-Hydroxy-7-oxo-5beta-cholanic acid7-Oxolithocholic acid3alpha-Hydroxy-7-oxo-5beta-cholan-24-oic AcidDTXSID501032263Y1357H1A28CHEBI:82679(3alpha,5beta)-3-Hydroxy-7-oxocholan-24-oic acidNSC-2261187-oxo-3alpha-hydroxycholan-24-oic acid
Show more names
3α-Hydroxy-7-oxo-5β-cholan-24-oic acid7-KLA3α-Hydroxy-7-ketocholanic acidChenodeoxycholic acid EP Impurity F3ALPHA-HYDROXY-7-KETO-5BETA-CHOLANIC ACID3-alpha-hydroxy-7-oxo-5-beta-cholan-24-oic acid
Cholan-24-oic acid, 3-hydroxy-7-oxo-, (3alpha,5beta)-3 alpha-ol-7-one-5 beta-cholanoic acidRefChem:546622(3 alpha,5 beta)-3-hydroxy-7-oxocholan-24-oic acidDTXCID801517272225-083-23.alpha.-Hydroxy-7-oxo-5.beta.-cholanic acid3a-Hydroxy-7-oxo-5b-cholanic acid

Database identifiers

CAS
4651-67-6
PubChem CID
444262
DTXSID
DTXSID501032263
ChEMBL
CHEMBL1254169
ChEBI
CHEBI:82679
UNII
Y1357H1A28
EC Number
225-083-2
Nikkaji
J297.868G

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
74.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
28

Experimental & physicochemical properties

Collision Cross Section · 1 item

200.3 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: Bile Acids];201.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids];201.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids];199.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids];189.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]

Physicochemical properties

Melting point
205 °C · 205°C
Boiling point
545.9 · 545.9±25.0 °C(Predicted)
Density
1.124 · 1.124±0.06 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
4.76 · 4.76±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 27.3% (3 of 11) of reports.

Warning

H302 (18.2%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (54.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (54.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 11 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 3 of 11 reports by companies.;There are 4 notifications provided by 8 of 11 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Active Update: 10-10-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/5428;Status: Active Update: 28-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21228
Hazard Classes and CategoriesAcute Tox. 4 (18.2%);Skin Irrit. 2 (54.5%);Eye Irrit. 2 (54.5%)

Regulatory information

Regulatory InformationStatus: Active Update: 10-10-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/5428;Status: Active Update: 28-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21228

Safety data

wgk
WGK 3
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H302

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationGastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Applications · 2 items

UsesNutriacholic Acid (Ursodeoxycholic Acid EP Impurity F) is derivative of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator.

Uses3alpha-Hydroxy-7-oxo-5beta-cholanic Acid is an intermediate in organic synthesis and pharmaceutical research and development. It can be used to synthesize the choleretic drug Obeticholic acid. Obeticholic acid can inhibit cholic acid synthesis. It is commonly used to treat primary biliary cirrhosis and nonalcoholic fatty liver disease.

Suppliers103 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Ark Pharm, Inc.847-367-3680 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 7-oxolithocholic acid is a bile acid that is lithocholic acid carrying an additional oxo substituent at position 7. It has a role as a human metabolite. It is a bile acid, a monohydroxy-5beta-cholanic acid, an oxo-5beta-cholanic acid and a 3alpha-hydroxy steroid. It is functionally related to a lithocholic acid. It is a conjugate acid of a 7-oxolithocholate.

Related reactions

8 records

Compound notes

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