Isoursodeoxycholic acid
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Basic information
- CAS
78919-26-3- Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
RUDATBOHQWOJDD-DNMBCGTGSA-N- Molecular formula
- C24H40O4
- Average molar mass
- 392.6 g/mol
- Monoisotopic mass
- 392.29265975
Overview
Isoursodeoxycholic acid is a dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by beta-hydroxy groups at positions 3 and 7. It has a role as a human metabolite. It is a conjugate acid of an isoursodeoxycholate.
Names & identifiers
- Preferred name
- Isoursodeoxycholic acid
- IUPAC
- (4R)-4-[(3S,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- English name
- (4R)-4-[(3S,5S,7S,8S,9S,10R,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- Molecular formula
- C24H40O4
- Molecular weight
- 392.57
Names & synonyms
Isoursodeoxycholic acid78919-26-33beta-Ursodeoxycholic Acid3beta,7beta-Dihydroxy-5beta-cholan-24-oic Acid2R6LC4J3N93beta,7beta-Dihydroxy-5beta-cholanoic acidCHEBI:43419DTXSID901318875Cholan-24-oic acid, 3,7-dihydroxy-, (3beta,5beta,7beta)-RefChem:150096DTXCID601743768isoUDCA
Show more names
3β-Ursodeoxycholic Acid3β-Ursodeoxycholic acidUrsodiol Impurity Hisoursodeoxycholicaci3-epi-Ursodeoxycholic acid3-Beta-Ursodeoxycholic AcidUrsodiol Related Compound HUrsodeoxycholic Acid impurity
3|A-Ursodeoxycholic Acid3b,7b-dihydroxy-5b-cholan-24-oic acidUrsodeoxycholic Acid EP Impurity HISO-URSODEOXYCHOLIC ACID(4R)-4-[(3S,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid3b-Ursodeoxycholic acidMFCD255632703?-Ursodeoxycholic Acid
Properties
Computed structural propertiesFilling in
- XLogP
- 4.9
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 605
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 184 · 184 - 186°C
- Boiling point
- 547.1 · 547.1±25.0 °C(Predicted)
- Density
- 1.128 · 1.128±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly, Heated)
- pka
- 4.76 · 4.76±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- RUDATBOHQWOJDD-FJNRGYSSNA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P321-P305+P351+P338-P332+P313-P362+P364-P337+P313
Chemistry & industry
Pharmacology
Metabolism/MetabolitesIsoursodeoxycholic acid has known human metabolites that include 3,6,7-Trihydroxycholan-24-oic acid and 4-(7-Hydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid.
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Applications
Uses3β-Ursodeoxycholic Acid (Ursodeoxycholic Acid EP Impurity H) is used as an anticholelithogenic.
UsesIsoursodeoxycholic acid is used as an anticholelithogenic.
Additional notes
DefinitionChEBI: A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by beta-hydroxy groups at positions 3 and 7.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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