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
Show more names
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
- Formal charge
- 0
- Complexity
- 645
Experimental & physicochemical properties
Collision Cross Section
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)
- form
- Solid
- color
- White to Off-White
- optical activity
- Consistent with structure
- Water Solubility
- 2.062 mg/L · 2.062mg/L at 25℃
- InChIKey
- DXOCDBGWDZAYRQ-QHVQYUNXNA-N
- SMILES
- C(O)(=O)CC[C@H]([C@@H]1[C@@]2(C)CC[C@]3([H])[C@@]4(C)CC[C@@H](O)C[C@@]4([H])CC(=O)[C@@]3([H])[C@]2([H])CC1)C |&1:5,6,7,11,13,17,20,25,27,r|
- LogP
- 3.48 at · 3.48 at 20℃
- FDA UNII
- 1357 H1A28 · Y1357H1A28
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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 information
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
- REACH Registrations
- Active
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Pharmacology
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers103 total
Additional notes
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
Compound notes
Loading…