Structure via PubChem · Public domain (PubChem)
(24S)-24-hydroxycholesterol
Sign in to saveAlso known as (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol, (24S)-cholest-5-ene-3beta,24-diol, (24S)-cholest-5-ene-3b,24-diol, cerebrosterol, 24S-hydroxycholesterol, 24(S)-hydroxycholesterol, 24S-cholest-5-ene-3b,24-diol, cerebrosterin
'24S-Hydroxycholesterol (24S-HC), also known as cholest-5-ene-3,24-diol or cerebrosterol', is an endogenous oxysterol produced by neurons in the brain to maintain cholesterol homeostasis. It was discovered in 1953 by Alberto Ercoli, S. Di Frisco, and Pietro de Ruggieri, who first isolated the molecule in the horse brain and then demonstrated its presence in the human brain.
In the Vinony graph
Within Vinony's link graph, (24S)-24-hydroxycholesterol is referenced by 494 other articles, and connects out to androstenedione, androstenediol and cholesterol 24-hydroxylase.
It is catalogued under topics including Chembox image size set, Cholestanes and Sterols.
Its subject is documented across 5 Wikipedia language editions.
Chemical data
- Formula
- C27H46O2
- Molecular weight
- 402.7 g/mol
- IUPAC name
- (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- InChIKey
- IOWMKBFJCNLRTC-XWXSNNQWSA-N
- XLogP
- 7
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- sterol
- Mass
- 402.349781
Show 5 more facts
- subject has role
- primary metabolite
- chemical formula
- C₂₇H₄₆O₂
- canonical SMILES
- CC(C)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
- isomeric SMILES
- C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- found in taxon
- Homo sapiens
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Structure
- Function
- References
'24S-Hydroxycholesterol (24S-HC), also known as cholest-5-ene-3,24-diol or cerebrosterol', is an endogenous oxysterol produced by neurons in the brain to maintain cholesterol homeostasis. It was discovered in 1953 by Alberto Ercoli, S. Di Frisco, and Pietro de Ruggieri, who first isolated the molecule in the horse brain and then demonstrated its presence in the human brain.
== Structure == 24S-HC is produced by a hydroxy group substitution at carbon number 24 in cholesterol, catalyzed by the enzyme cholesterol 24-hydroxylase (CYP46A1).
Excerpted from Wikipedia’s “(24S)-24-hydroxycholesterol” article, available under the CC BY-SA 4.0 licence.