3,7-Dihydroxycholestan-26-oic acid
Basic information
- CAS
17974-66-2- Standard SMILES
CC(CCC[C@@H](C)C1CCC2C3C(CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)C(=O)O- InChIKey
ITZYGDKGRKKBSN-SQZYAAIWSA-N- Molecular formula
- C27H46O4
- Average molar mass
- 434.7 g/mol
- Monoisotopic mass
- 434.33960994
Overview
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Names & identifiers
- Preferred name
- 3,7-Dihydroxycholestan-26-oic acid
- IUPAC
- (6R)-6-[(3R,5S,7R,10S,13R)-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]-2-methylheptanoic acid
- English name
- (6R)-6-[(3R,5S,7R,10S,13R)-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]-2-methylheptanoic acid
- Molecular formula
- C27H46O4
- Molecular weight
- 434.65
Names & synonyms
DTXSID709392523,7-dihydroxycholestan-26-oic acidRefChem:9107763,7-DHCADTXCID3013677553alpha,7alpha-Dihydroxy-5beta-cholestanate3alpha,7alpha-Dihydroxy-5beta-cholestanoateC04554(8xi,9xi,14xi,17xi)-3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acid3a,7a-Dihydroxycoprostanic acid3Alpha,7Alpha-Dihydroxycoprostanic Acid-DihydroxycoprostanicAcid
Show more names
3α,7α-Dihydroxycoprostanic acid3α,7α-dihydroxy-5β-cholestanoic acid3α,7α-Dihydroxy-5β-cholest-26-oic acid3α,7α-Dihydroxy-5β-cholestan-26-oic acid(25RS)-3α,7α-dihydroxy-5β-cholestan-26-oic acid(6R)-6-[(3R,5S,7R,10S,13R)-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]-2-methylheptanoic acid
Properties
Computed structural properties
- XLogP
- 6.6
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 664
Physicochemical properties
- Boiling point
- 574.184 · 574.184±25.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.093 · 1.093±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 4.808 · 4.808±0.21(predicted)
- color
- White to Off-White
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 21 · NA.21
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Uses3a,7a-Dihydroxycoprostanic Acid is a precursor of Cholic Acid (C432600), it undergoes side chain oxidation during the synthesis of bile acids. It was found that Zellweger’s syndrome patients have abnormal mitochondrial structure, the organelle that is responsible for the side chain oxidation, and as a consequence, excess amounts of 3a,7a-Dihydroxycoprostanic Acid.
Additional notes
DefinitionChEBI: 3alpha,7alpha-dihydroxy-5beta-cholestan-26-oic acid is a cholestanoid that is 5beta-cholestan-26-oic acid substituted by alpha-hydroxy groups at positions 3 and 7 respectively. It has a role as a human metabolite and a mouse metabolite. It is a dihydroxy monocarboxylic acid, a 7alpha-hydroxy steroid, a 3alpha-hydroxy steroid and a cholestanoid. It derives from a hydride of a 5beta-cholestane.
Related reactions
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Compound notes
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