CHEBI:85778 - 4β-hydroxycholesterol

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ChEBI Name 4β-hydroxycholesterol
ChEBI ID CHEBI:85778
ChEBI ASCII Name 4beta-hydroxycholesterol
Definition A oxysterol that is cholesterol in which the hydrogen at the 4β position has been replaced by a hydroxy group. A metabolite of cholesterol formed by the drug-metabolizing enzyme cytochrome P450 3A4, it is one of the major oxysterols in the human circulation.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Nevila Nouspikel
Supplier Information ChemicalBook:CB3350290, eMolecules:31430156, ZINC000005759161
Download Molfile XML SDF
Formula C27H46O2
Net Charge 0
Average Mass 402.65290
Monoisotopic Mass 402.34978
InChI InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChIKey CZDKQKOAHAICSF-JSAMMMMSSA-N
SMILES CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4β-hydroxycholesterol (CHEBI:85778) has functional parent cholesterol (CHEBI:16113)
4β-hydroxycholesterol (CHEBI:85778) has role human metabolite (CHEBI:77746)
4β-hydroxycholesterol (CHEBI:85778) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
4β-hydroxycholesterol (CHEBI:85778) is a 3β-sterol (CHEBI:35348)
4β-hydroxycholesterol (CHEBI:85778) is a diol (CHEBI:23824)
4β-hydroxycholesterol (CHEBI:85778) is a oxysterol (CHEBI:53030)
IUPAC Name
cholest-5-ene-3β,4β-diol
Synonyms Sources
(3β,4β)-cholest-5-ene-3,4-diol IUPAC
4β-hydroxycholesterol UniProt
cholest-5-en-3β,4β-diol LIPID MAPS
Manual Xrefs Databases
HMDB0013643 HMDB
LMST01010014 LIPID MAPS
View more database links
Registry Number Type Source
17320-10-4 CAS Registry Number ChemIDplus
Citations
Goodenough AK, Onorato JM, Ouyang Z, Chang S, Rodrigues AD, Kasichayanula S, Huang SP, Turley W, Burrell R, Bifano M, Jemal M, LaCreta F, Tymiak A, Wang-Iverson D (2011)
Quantification of 4-beta-hydroxycholesterol in human plasma using automated sample preparation and LC-ESI-MS/MS analysis.
Chemical research in toxicology 24, 1575-1585 [PubMed:21728364]
[show Abstract]
Diczfalusy U, Kanebratt KP, Bredberg E, Andersson TB, Böttiger Y, Bertilsson L (2009)
4beta-hydroxycholesterol as an endogenous marker for CYP3A4/5 activity. Stability and half-life of elimination after induction with rifampicin.
British journal of clinical pharmacology 67, 38-43 [PubMed:19006545]
[show Abstract]
Tomalik-Scharte D, Lütjohann D, Doroshyenko O, Frank D, Jetter A, Fuhr U (2009)
Plasma 4beta-hydroxycholesterol: an endogenous CYP3A metric?
Clinical pharmacology and therapeutics 86, 147-153 [PubMed:19458613]
[show Abstract]
Wide K, Larsson H, Bertilsson L, Diczfalusy U (2008)
Time course of the increase in 4beta-hydroxycholesterol concentration during carbamazepine treatment of paediatric patients with epilepsy.
British journal of clinical pharmacology 65, 708-715 [PubMed:18279471]
[show Abstract]
Diczfalusy U, Miura J, Roh HK, Mirghani RA, Sayi J, Larsson H, Bodin KG, Allqvist A, Jande M, Kim JW, Aklillu E, Gustafsson LL, Bertilsson L (2008)
4Beta-hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians.
Pharmacogenetics and genomics 18, 201-208 [PubMed:18300941]
[show Abstract]
Bodin K, Andersson U, Rystedt E, Ellis E, Norlin M, Pikuleva I, Eggertsen G, Björkhem I, Björkhem I, Diczfalusy U (2002)
Metabolism of 4 beta -hydroxycholesterol in humans.
The Journal of biological chemistry 277, 31534-31540 (Source: SUBMITTER) [PubMed:12077124]
[show Abstract]
Bodin K, Bretillon L, Aden Y, Bertilsson L, Broomé U, Einarsson C, Diczfalusy U (2001)
Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4.
The Journal of biological chemistry 276, 38685-38689 [PubMed:11514559]
[show Abstract]
Breuer O (1995)
Identification and quantitation of cholest-5-ene-3 beta,4 beta-diol in rat liver and human plasma.
Journal of lipid research 36, 2275-2281 (Source: SUBMITTER) [PubMed:8656065]
[show Abstract]
Last Modified
25 April 2017