Basic information
- CAS
4725-24-0- Standard SMILES
CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
RXMHNAKZMGJANZ-DTTSCKGMSA-N- Molecular formula
- C27H46O3
- Average molar mass
- 418.7 g/mol
- Monoisotopic mass
- 418.34469533
Overview
7alpha,26-dihydroxycholesterol is an oxysterol that is cholesterol which is substituted by hydroxy groups at the 7alpha and 26 positions. It has a role as a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a triol, a 7alpha-hydroxy steroid, a 26-hydroxy steroid and an oxysterol. It is functionally related to a cholesterol.
Names & identifiers
- Preferred name
- 7alpha,27-Dihydroxycholesterol
- IUPAC
- (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
- English name
- (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
- Molecular formula
- C27H46O3
- Molecular weight
- 418.65
Names & synonyms
7alpha,27-dihydroxycholesterol4725-24-0Cholest-5-ene-3beta,7alpha,26-triolCholest-5-ene-3,7,27-triol5-Cholestene-3beta,7alpha,26-triolcholest-5-ene-3beta,7alpha,27-triolDTXSID701311542(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol(3S,7S,8S,9S,10R,13R,14S,17R)-17-((2R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthrene-3,7-diolRefChem:106601DTXCID601741374(3S,7S,8S,9S,10R,13R,14S,17R)-17-((2R,6R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthrene-3,7-diol
Show more names
Cholesterol Impurity 347α,27-dihydroxycholesterol7-alpha,27-DihydroxycholesterolCholest-5-ene-3,7,26-triol, (3β,7α)-(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Properties
Computed structural properties
- XLogP
- 6
- Topological polar surface area
- 60.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 644
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C27 bile acids, alcohols, and derivatives [ST0403]
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 552.6 · 552.6±35.0 °C(Predicted)
- Density
- 1.08 · 1.08±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 14.11 · 14.11±0.70(Predicted)
- form
- powder
- color
- White to off-white
- InChIKey
- RXMHNAKZMGJANZ-DTTSCKGMSA-N
- SMILES
- O[C@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(CO)C)C)(CC[C@@H]2[C@]4(CC[C@@H](CC4=C1)O)C)C
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- 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
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
Applications
Uses7α,27-Dihydroxycholesterol is used in the study of immunochemistry. It is a potent and selective agonist of EB12.7α,27-Dihydroxycholesterol is also studied in biochemical methods as one of several oxysterols found in human plasma using HPLC-MS and incorporating charg-tagging and high-resolution mass spectrometry.
Suppliers9 total
Aladdin Scientific[email protected]
金克隆（北京）生物技术有限公司400-910-1997 15330005590 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
Creative Enzymes1-516-855-7709 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
上海贝万塔生物科技有限公司021-67187366 19901745723 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
广州优南科技有限公司
Related reactions
0 records
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Compound notes
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