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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:(24S)-24-hydroxycholesterol
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Accession:CHEBI:34310 term browser browse the term
Definition:A 24-hydroxycholesterol that has S configuration at position 24. It is the major metabolic breakdown product of cholesterol in the brain.
Synonyms:related_synonym: (24S)-cholest-5-ene-3beta,24-diol;   (3beta,24S)-cholest-5-ene-3,24-diol;   24(S)-hydroxycholesterol;   24-Hydroxycholesterol;   24S-OHC;   24S-hydroxy-cholesterol;   24S-hydroxycholesterol;   Cerebrosterol;   Cholest-5-ene-3,24-diol;   Formula=C27H46O2;   InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1;   InChIKey=IOWMKBFJCNLRTC-XWXSNNQWSA-N;   SMILES=[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C;   cholest-5-en-3beta,24S-diol
 xref: Beilstein:3218472;   CAS:474-73-7;   Chemspider:108790;   FooDB:FDB022611;   HMDB:HMDB0001419;   KEGG:C13550;   LIPID_MAPS_instance:LMST01010019
 xref_mesh: MESH:C044563
 xref: MetaCyc:CPD-7239;   PMCID:PMC3846912;   PMID:10884051;   PMID:14574622;   PMID:15061359;   PMID:20671299;   PMID:25539717;   PMID:25577946;   PMID:26745248;   PMID:28153530;   PMID:28322741;   PMID:28346482;   PMID:28576383;   PMID:29462682;   PMID:29550246;   PMID:30029553;   PMID:30245667;   PMID:30594698;   PMID:30802527;   PMID:31136842;   PMID:31322567;   PMID:31654618;   PMID:31981724;   PMID:32169014;   PMID:32382321;   PMID:32392803;   PMID:32855525;   PMID:33051477;   PMID:33118626;   PMID:33192294;   PMID:33219208;   PMID:33561510;   PMID:33792095;   PMID:33837574


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(24S)-24-hydroxycholesterol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abca1 ATP binding cassette subfamily A member 1 increases expression ISO 24-hydroxycholesterol results in increased expression of ABCA1 mRNA; 24-hydroxycholesterol results in increased expression of ABCA1 protein CTD PMID:15148325 PMID:19126211 NCBI chr 5:67,678,267...67,801,162
Ensembl chr 5:67,681,297...67,801,170
JBrowse link
G Abcg1 ATP binding cassette subfamily G member 1 increases expression ISO 24-hydroxycholesterol results in increased expression of ABCG1 protein CTD PMID:19126211 NCBI chr20:9,126,687...9,182,948
Ensembl chr20:9,126,687...9,182,948
JBrowse link
G App amyloid beta precursor protein multiple interactions
increases metabolic processing
ISO 24-hydroxycholesterol affects the metabolism of and results in increased activity of APP protein; 24-hydroxycholesterol results in decreased metabolism of and results in decreased secretion of APP protein
24-hydroxycholesterol results in increased metabolism of APP protein
CTD PMID:15148325 PMID:17532301 PMID:19126211 NCBI chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 increases expression
multiple interactions
ISO 24-hydroxycholesterol results in increased expression of CCL2 mRNA
[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of CCL2 mRNA; Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of CCL2 mRNA]; Quercetin analog inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of CCL2 mRNA]
CTD PMID:24802026 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Cd36 CD36 molecule increases expression
multiple interactions
ISO 24-hydroxycholesterol results in increased expression of CD36 mRNA
[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of CD36 mRNA; Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of CD36 mRNA]; Quercetin analog inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of CD36 mRNA]; Quercetin inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of CD36 mRNA]
CTD PMID:24802026 NCBI chr 4:17,317,343...17,410,084 JBrowse link
G Cyp27a1 cytochrome P450, family 27, subfamily a, polypeptide 1 decreases abundance ISO CYP27A1 protein results in decreased abundance of 24-hydroxycholesterol CTD PMID:12119285 NCBI chr 9:76,264,655...76,294,551
Ensembl chr 9:76,264,860...76,294,551
JBrowse link
G Cyp39a1 cytochrome P450, family 39, subfamily a, polypeptide 1 increases metabolic processing ISO CYP39A1 protein results in increased metabolism of 24-hydroxycholesterol CTD PMID:10748047 NCBI chr 9:17,230,455...17,306,775
Ensembl chr 9:17,230,455...17,306,775
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions ISO [24-hydroxycholesterol co-treated with NR1H3 protein] results in increased expression of CYP3A4 mRNA CTD PMID:23732298 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Cyp46a1 cytochrome P450, family 46, subfamily a, polypeptide 1 affects abundance
increases chemical synthesis
increases metabolic processing
ISO CYP46A1 gene SNP affects the abundance of 24-hydroxycholesterol
CYP46A1 protein results in increased chemical synthesis of 24-hydroxycholesterol
CYP46A1 protein results in increased metabolism of 24-hydroxycholesterol
CTD PMID:14640697 PMID:19286353 NCBI chr 6:127,243,315...127,274,765
Ensembl chr 6:127,243,315...127,274,760
JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 increases metabolic processing ISO CYP7A1 protein results in increased metabolism of 24-hydroxycholesterol CTD PMID:11013305 NCBI chr 5:19,376,979...19,386,676
Ensembl chr 5:19,376,974...19,386,688
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions ISO 24-hydroxycholesterol binds to and results in decreased activity of ESR1 protein; 24-hydroxycholesterol inhibits the reaction [Estradiol results in increased activity of ESR1 protein] CTD PMID:17873880 NCBI chr 1:41,106,335...41,499,104
Ensembl chr 1:41,210,475...41,495,002
JBrowse link
G Esr2 estrogen receptor 2 multiple interactions ISO 24-hydroxycholesterol binds to and results in decreased activity of ESR2 protein; 24-hydroxycholesterol inhibits the reaction [Estradiol results in increased activity of ESR2 protein] CTD PMID:17873880 NCBI chr 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919
JBrowse link
G Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase decreases activity ISO 24-hydroxycholesterol results in decreased activity of HMGCR protein CTD PMID:7751816 NCBI chr 2:27,997,523...28,018,983
Ensembl chr 2:27,997,525...28,019,703
JBrowse link
G Itgb1 integrin subunit beta 1 increases expression
multiple interactions
ISO 24-hydroxycholesterol results in increased expression of ITGB1 mRNA
[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of ITGB1 mRNA; Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of ITGB1 mRNA]; Quercetin analog inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of ITGB1 mRNA]; Quercetin inhibits the reaction [24-hydroxycholesterol results in increased expression of ITGB1 mRNA]; Quercetin inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of ITGB1 mRNA]
CTD PMID:24802026 NCBI chr19:56,705,123...56,753,199
Ensembl chr19:56,705,171...56,753,195
JBrowse link
G Mmp9 matrix metallopeptidase 9 increases expression
multiple interactions
ISO 24-hydroxycholesterol results in increased expression of MMP9 mRNA
Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of MMP9 mRNA]
CTD PMID:24802026 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Nr1h3 nuclear receptor subfamily 1, group H, member 3 multiple interactions ISO [24-hydroxycholesterol co-treated with NR1H3 protein] results in increased expression of CYP3A4 mRNA CTD PMID:23732298 NCBI chr 3:77,158,808...77,168,907
Ensembl chr 3:77,158,808...77,168,722
JBrowse link
G Ptges prostaglandin E synthase multiple interactions
increases expression
ISO Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of PTGES mRNA]; Quercetin inhibits the reaction [24-hydroxycholesterol results in increased expression of PTGES mRNA] CTD PMID:24802026 NCBI chr 3:14,177,892...14,189,236 JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression
multiple interactions
ISO 24-hydroxycholesterol results in increased expression of PTGS2 protein
[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of PTGS2 protein
CTD PMID:24802026 NCBI chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Th tyrosine hydroxylase multiple interactions ISO 24-hydroxycholesterol results in increased expression of and results in increased phosphorylation of TH protein CTD PMID:19014385 NCBI chr 1:198,071,500...198,078,832
Ensembl chr 1:198,071,503...198,109,767
JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions
increases expression
ISO [24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of TLR4 mRNA; Quercetin analog inhibits the reaction [24-hydroxycholesterol results in increased expression of TLR4 mRNA]; Quercetin analog inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of TLR4 mRNA]; Quercetin inhibits the reaction [24-hydroxycholesterol results in increased expression of TLR4 mRNA]; Quercetin inhibits the reaction [[24-hydroxycholesterol co-treated with 27-hydroxycholesterol co-treated with cholest-5-en-3 beta,7 alpha-diol] results in increased expression of TLR4 mRNA] CTD PMID:24802026 NCBI chr 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19821
    role 19769
      application 19481
        indicator 8687
          biomarker 6469
            (24S)-24-hydroxycholesterol 20
              (24S)-24-hydroxycholesterol ester + 0
              (24S)-hydroxycholesterol 24-sulfate 0
              (24S)-hydroxycholesterol 3,24-disulfate 0
              (24S)-hydroxycholesterol 3-sulfate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic molecule 19569
                              organic cyclic compound 19360
                                organic polycyclic compound 16538
                                  steroid 13057
                                    hydroxy steroid 12658
                                      3-hydroxy steroid 10368
                                        3beta-hydroxy steroid 2014
                                          3beta-hydroxy-Delta(5)-steroid 1849
                                            cholesterol 334
                                              oxysterol 106
                                                24-hydroxycholesterol 20
                                                  (24S)-24-hydroxycholesterol 20
                                                    (24S)-24-hydroxycholesterol ester + 0
                                                    (24S)-hydroxycholesterol 24-sulfate 0
                                                    (24S)-hydroxycholesterol 3,24-disulfate 0
                                                    (24S)-hydroxycholesterol 3-sulfate 0
paths to the root