Cholenic acid
Basic information
- CAS
5255-17-4- Standard SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
HIAJCGFYHIANNA-QIZZZRFXSA-N- Molecular formula
- C24H38O3
- Average molar mass
- 374.6 g/mol
- Monoisotopic mass
- 374.28209507
Overview
3b-Hydroxy-5-cholenoic acid is a steroid.
Names & identifiers
- Preferred name
- Cholenic acid
- IUPAC
- (4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
- English name
- 3BETA-HYDROXY-DELTA5-CHOLENIC ACID
- Molecular formula
- C24H38O3
- Molecular weight
- 374.57
Names & synonyms
Cholenic acidDTXSID901317558(4R)-4-[(1R,3aS,3bS,7S,9aR,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]pentanoic acid(4R)-4-((1R,3aS,3bS,7S,9aR,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta(a)phenanthren-1-yl)pentanoic acidRefChem:576020DTXCID801747366973-563-15255-17-43b-hydroxy-5-cholenoic acid3beta-Hydroxy-delta5-cholenic acid3beta-Hydroxy-5-cholenic acid3beta-Hydroxy-5-cholenoic acid
Show more names
5-cholenic acid-3β-ol(R)-4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acidZK-1157573β-Hydroxy-Δ5<5-Cholenic Acid-32-olCarpropamid Impurity 93β-Hydroxycholenic Acid
5-cholenic acid-3B-ol3beta-Hydroxychol-5-en-24-oic acidCholenateD5-CholenateMFCD00069468(4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid3beta-Hydroxy-chol-5-en-24-oic Acid3beta-Hydroxy-chol-5-en-24-oate
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 625
Experimental & physicochemical properties
Chemical ClassesBile Acids -> Canonical Bile Acids
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]
Physical DescriptionSolid
Collision Cross Section184.1 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
Physicochemical properties
- Melting point
- 232 °C · 232°C
- Boiling point
- 522.8 · 522.8±23.0 °C(Predicted)
- Density
- 1.11 · 1.11±0.1 g/cm3(Predicted)
- refractive index
- -39.5 ° · -39.5 ° (C=1, Dioxane)
- storage temp.
- Refrigerator
- solubility
- Dioxane (Slightly, Sonicated), DMF (Slightly), DMSO (Slightly, Heated, Sonicated)
- form
- Solid
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
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P264+P265, P280, P302+P352, P305+P351+P338, P317, P321, P337+P317, P362+P364, and P501 (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 CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionCholenic acid is a monohydroxy bile acid. It is a cholesterol oxidation product formed by 7α-hydroxylation of 27-hydroxycholesterol (Item Nos. 14790 | 14791), as well as a precursor in the biosynthesis of chenodeoxycholic acid . Levels of cholenic acid are increased in patients with neonatal liver disease harboring mutations in CYP7A1, the gene encoding 7α-hydroxylase, as well as in patients with intrahepatic and extrahepatic cholestasis.
Uses5-Cholenic Acid-3β-ol is a bile acid of which the metabolism in humans results in the primary bile acids lithocholic acid and chenodeoxycholic. It is found in hgher concentrations in meconium of premature human babies when compared to full term babies.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: 3b-Hydroxy-5-cholenoic acid is a steroid.
Suppliers
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Compound notes
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