3,7-Dioxo-5beta-cholanoic acid
Basic information
- CAS
859-97-2- 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[C@]12C- InChIKey
IOOKJGQHLHXYEF-FFFIEFPASA-N- Molecular formula
- C24H36O4
- Average molar mass
- 388.5 g/mol
- Monoisotopic mass
- 388.26135963
Overview
3,7-Diketocholanic acid is a bile acid.
Names & identifiers
- Preferred name
- 3,7-Dioxo-5beta-cholanoic acid
- IUPAC
- (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- English name
- 3,7-DIKETO-5BETA-CHOLAN-24-OIC ACID
- Molecular formula
- C24H36O4
- Molecular weight
- 388.54
Names & synonyms
3,7-Dioxo-5beta-cholanoic acid859-97-2DTXSID701033867RefChem:1066158DTXCID501518633(4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid3,7-Dioxo-5beta-cholan-24-oic Acid(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidCHEMBL1254261CCRIS 39883,7-diketocholanic acid3,7-Diketochenodeoxycholic acid
Show more names
3,7-di-KETO3.7-Diketocholansaeure5B-cholanic acid 3,7-dione5β-cholanic acid-3,7-dione3,7-Diketo-5β-cholanic acid5β-CHOLANIC acid-3, 7-DIONEDehydrochenodeoxycholic acid5BETA-CHOLANIC ACID-3,7-DIONE
3,7-diketone3,7-Diketo-CA5.beta.-Cholan-24-oic acid, 3,7-dioxo-Cholan-24-oic acid, 3,7-dioxo-, (5.beta.)-SCHEMBL966480Chenodeoxycholic acid, dehydro-orb31810773,7-dioxo-5beta-cholanic acid
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 71.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 684
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physicochemical properties
- Melting point
- 152 °C · 152 °C
- Boiling point
- 544.7 · 544.7±25.0 °C(Predicted)
- Density
- 1.12 · 1.120±0.06 g/cm3(Predicted)
- pka
- 4.76 · 4.76±0.10(Predicted)
Chemistry & industry
Applications
UsesDehydrochenodeoxycholic Acid is a compound involved in a study of novel camptothecin-bile acid analogues which showed improved lactone-stability in rat serum and antitumor targeting, cytotoxicity against human liver cancer, colon cancer and cervical cancer cells.
Additional notes
DefinitionChEBI: 3,7-Diketocholanic acid is a bile acid.
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