24(S),25-epoxycholesterol (CHEBI:41633)

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CHEBI:41633 - 24(S),25-epoxycholesterol

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ChEBI Name	24(S),25-epoxycholesterol

ChEBI ID	CHEBI:41633

ChEBI ASCII Name	24(S),25-epoxycholesterol

Definition	A 3β-hydroxy-Δ⁵-steroid that is desmosterol in which the double bond at position 24-25 has been oxidised to the corresponding epoxide (the 24S diastereoisomer). It is an oxysterol agonist of the liver X receptor.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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3 32 1 0 0 0

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4 5 2 0 0 0

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28 29 1 0 0 0

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28 71 1 0 0 0

29 72 1 0 0 0

29 73 1 0 0 0

M END): 29 ms

reading 73 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

73 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Formula

C27H44O2

Net Charge

Average Mass

400.63710

Monoisotopic Mass

400.33413

InChI

InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1

InChIKey

OSENKJZWYQXHBN-XVYZBDJZSA-N

SMILES

C[C@H](CC[C@@H]1OC1(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Roles Classification
Biological Role(s):	liver X receptor agonist Any compound that acts as an agonist towards the liver X receptors.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	24(S),25-epoxycholesterol (CHEBI:41633) has functional parent desmosterol (CHEBI:17737) 24(S),25-epoxycholesterol (CHEBI:41633) has role liver X receptor agonist (CHEBI:86029) 24(S),25-epoxycholesterol (CHEBI:41633) is a 3β-hydroxy-Δ⁵-steroid (CHEBI:1722) 24(S),25-epoxycholesterol (CHEBI:41633) is a cholestanoid (CHEBI:50401) 24(S),25-epoxycholesterol (CHEBI:41633) is a epoxy steroid (CHEBI:145217)

IUPAC Name

(24S)-24,25-epoxycholest-5-en-3β-ol

Synonyms	Sources
(24S)-24,25-epoxycholesterol	ChEBI
(24S)-25-epoxycholesterol	UniProt
(3β,24S)-24,25-epoxycholest-5-en-3-ol	IUPAC
24(S),25-EC	ChEBI
24,25-epoxy-cholesterol	LIPID MAPS
24S,25-epoxy-cholest-5-en-3β-ol	LIPID MAPS
24S,25-epoxy-cholesterol	LIPID MAPS

Manual Xrefs	Databases
C15632	KEGG COMPOUND
CO1	PDBeChem
LMST01010012	LIPID MAPS
LSM-5712	LINCS
View more database links

Registry Numbers	Types	Sources
5765150	Reaxys Registry Number	Reaxys
77058-74-3	CAS Registry Number	KEGG COMPOUND

Citations	Types	Sources
19426978	PubMed citation	Europe PMC
20854813	PubMed citation	Europe PMC
22178193	PubMed citation	Europe PMC
22713431	PubMed citation	Europe PMC
23130136	PubMed citation	Europe PMC
23292650	PubMed citation	Europe PMC
23455994	PubMed citation	Europe PMC
24491562	PubMed citation	Europe PMC
24747199	PubMed citation	Europe PMC
24832732	PubMed citation	Europe PMC

Last Modified

28 October 2019

CHEBI:41633 - 24(S),25-epoxycholesterol

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