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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:25-hydroxycholesterol
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Accession:CHEBI:42977 term browser browse the term
Definition:A 25-hydroxy steroid that has formula 402.65294.
Synonyms:related_synonym: 5-Cholestene-3beta,25-diol;   Cholest-5-ene-3beta,25-diol;   Formula=C27H46O2;   InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1;   InChIKey=INBGSXNNRGWLJU-ZHHJOTBYSA-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)CCCC(C)(C)O
 alt_id: CHEBI:37616;   CHEBI:42972
 xref: CAS:2140-46-7;   KEGG:C15519;   LIPID_MAPS_instance:LMST01010018
 xref_mesh: MESH:C007997



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25-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
multiple interactions
ISO
EXP
25-hydroxycholesterol results in increased expression of ABCA1 mRNA
[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA; [25-hydroxycholesterol co-treated with alitretinoin] results in increased expression of ABCA1 protein; [9-deoxy-delta-9-prostaglandin D2 binds to and results in increased activity of PPARG protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]; [Bezafibrate binds to and results in increased activity of PPARA protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]
[Cholesterol co-treated with 25-hydroxycholesterol] results in decreased expression of ABCA1 mRNA
CTD PMID:12595494 PMID:16023994 PMID:17526932 PMID:19260826 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 25-hydroxycholesterol results in increased expression of ABCG1 mRNA CTD PMID:31011801 NCBI chr20:9,126,687...9,182,948
Ensembl chr20:9,126,687...9,182,948
JBrowse link
G Acta2 actin alpha 2, smooth muscle increases expression
multiple interactions
EXP 25-hydroxycholesterol results in increased expression of ACTA2 mRNA
15-deoxyprostaglandin J2 inhibits the reaction [25-hydroxycholesterol results in increased expression of ACTA2 mRNA]; alitretinoin promotes the reaction [25-hydroxycholesterol results in increased expression of ACTA2 mRNA]
CTD PMID:17161435 NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
JBrowse link
G Adipor1 adiponectin receptor 1 multiple interactions
decreases expression
ISO [25-hydroxycholesterol co-treated with alitretinoin] results in decreased expression of ADIPOR1 mRNA
25-hydroxycholesterol results in decreased expression of ADIPOR1 mRNA
CTD PMID:16023994 NCBI chr13:45,859,461...45,879,248
Ensembl chr13:45,859,533...45,879,241
JBrowse link
G Casp3 caspase 3 multiple interactions
increases activity
ISO
EXP
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP3 protein]; Acetylcysteine inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP3 protein]; BAY 11-7085 inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP3 protein]; quercetin 3-O-beta-(2''-galloyl)-rhamnopyranoside inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP3 protein] CTD PMID:25845326 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 increases activity
multiple interactions
EXP 25-hydroxycholesterol results in increased activity of CASP8 protein
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP8 protein]; Acetylcysteine inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP8 protein]; BAY 11-7085 inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP8 protein]; quercetin 3-O-beta-(2''-galloyl)-rhamnopyranoside inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP8 protein]
CTD PMID:25845326 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 increases activity
multiple interactions
EXP 25-hydroxycholesterol results in increased activity of CASP9 protein
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP9 protein]; Acetylcysteine inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP9 protein]; BAY 11-7085 inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP9 protein]; quercetin 3-O-beta-(2''-galloyl)-rhamnopyranoside inhibits the reaction [25-hydroxycholesterol results in increased activity of CASP9 protein]
CTD PMID:25845326 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Cdkn1b cyclin-dependent kinase inhibitor 1B increases expression EXP 25-hydroxycholesterol results in increased expression of CDKN1B mRNA CTD PMID:17161435 NCBI chr 4:167,760,067...167,765,177
Ensembl chr 4:167,760,181...167,764,982
JBrowse link
G Cnn1 calponin 1 multiple interactions
increases expression
EXP 15-deoxyprostaglandin J2 inhibits the reaction [25-hydroxycholesterol results in increased expression of CNN1 mRNA]; alitretinoin promotes the reaction [25-hydroxycholesterol results in increased expression of CNN1 mRNA] CTD PMID:17161435 NCBI chr 8:20,632,434...20,641,097
Ensembl chr 8:20,632,338...20,641,098
JBrowse link
G Cyp27a1 cytochrome P450, family 27, subfamily a, polypeptide 1 multiple interactions
increases chemical synthesis
ISO [CYP27A1 protein results in increased metabolism of Cholesterol] which results in increased chemical synthesis of 25-hydroxycholesterol
CYP27A1 protein results in increased chemical synthesis of 25-hydroxycholesterol
CTD PMID:8078928 PMID:17890683 NCBI chr 9:76,264,655...76,294,551
Ensembl chr 9:76,264,860...76,294,551
JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 increases metabolic processing ISO
EXP
CYP7A1 protein results in increased metabolism of 25-hydroxycholesterol CTD PMID:10882719 NCBI chr 5:19,376,979...19,386,676
Ensembl chr 5:19,376,974...19,386,688
JBrowse link
G Cyp7b1 cytochrome P450 family 7 subfamily B member 1 increases metabolic processing
increases abundance
ISO CYP7B1 protein results in increased metabolism of 25-hydroxycholesterol
CYP7B1 gene mutant form results in increased abundance of 25-hydroxycholesterol
CTD PMID:10748047 NCBI chr 2:100,502,791...100,669,713
Ensembl chr 2:100,502,791...100,669,698
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions ISO 25-hydroxycholesterol binds to and results in decreased activity of ESR1 protein; 25-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 25-hydroxycholesterol binds to and results in decreased activity of ESR2 protein; 25-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 Fads1 fatty acid desaturase 1 multiple interactions
decreases expression
ISO 25-hydroxycholesterol inhibits the reaction [beta-hydroxy simvastatin acid results in increased expression of FADS1 mRNA]
25-hydroxycholesterol results in decreased expression of FADS1 mRNA
CTD PMID:17655842 NCBI chr 1:206,827,724...206,842,734
Ensembl chr 1:206,827,765...206,842,734
JBrowse link
G Fas Fas cell surface death receptor increases expression ISO 25-hydroxycholesterol results in increased expression of FAS mRNA CTD PMID:19260826 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591
JBrowse link
G Fhl1 four and a half LIM domains 1 multiple interactions
increases expression
EXP 15-deoxyprostaglandin J2 inhibits the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA]; alitretinoin promotes the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA]; Brefeldin A inhibits the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA]; Cycloheximide promotes the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA]; Dactinomycin promotes the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA]; Genistein inhibits the reaction [25-hydroxycholesterol results in increased expression of FHL1 mRNA] CTD PMID:17161435 NCBI chr  X:134,555,399...134,614,930
Ensembl chr  X:134,555,479...134,614,928
JBrowse link
G Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase multiple interactions
decreases expression
decreases activity
ISO
EXP
[25-hydroxycholesterol co-treated with Cholesterol] results in decreased activity of HMGCR protein; [25-hydroxycholesterol co-treated with Mevalonic Acid] results in increased ubiquitination of HMGCR protein; Dehydroepiandrosterone inhibits the reaction [25-hydroxycholesterol results in decreased activity of HMGCR protein]; LDLR gene mutant form promotes the reaction [[25-hydroxycholesterol co-treated with Cholesterol] results in decreased activity of HMGCR protein]; Pregnenolone inhibits the reaction [25-hydroxycholesterol results in decreased activity of HMGCR protein]
25-hydroxycholesterol results in decreased expression of HMGCR protein
25-hydroxycholesterol metabolite results in decreased activity of HMGCR protein; 25-hydroxycholesterol results in decreased activity of HMGCR protein
25-hydroxycholesterol results in decreased expression of HMGCR mRNA; 25-hydroxycholesterol results in decreased expression of HMGCR protein
CTD PMID:7749852 PMID:7751816 PMID:9059514 PMID:12477733 PMID:18024962 More... NCBI chr 2:27,997,523...28,018,983
Ensembl chr 2:27,997,525...28,019,703
JBrowse link
G Il1b interleukin 1 beta multiple interactions
increases secretion
increases expression
ISO 25-hydroxycholesterol promotes the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]
25-hydroxycholesterol results in increased secretion of IL1B protein
25-hydroxycholesterol results in increased expression of IL1B mRNA
CTD PMID:11851725 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il6 interleukin 6 increases secretion
multiple interactions
ISO
EXP
25-hydroxycholesterol results in increased secretion of IL6 protein
25-hydroxycholesterol inhibits the reaction [IL6 protein results in increased phosphorylation of STAT3 protein]
25-hydroxycholesterol inhibits the reaction [Lipopolysaccharides results in increased secretion of IL6 protein]
CTD PMID:11851725 PMID:27052460 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Inha inhibin subunit alpha increases expression EXP 25-hydroxycholesterol results in increased expression of INHA mRNA; 25-hydroxycholesterol results in increased expression of INHA protein CTD PMID:19464342 NCBI chr 9:76,994,465...76,997,366
Ensembl chr 9:76,993,589...76,997,248
JBrowse link
G Inhba inhibin subunit beta A increases expression
decreases expression
EXP 25-hydroxycholesterol results in increased expression of INHBA mRNA
25-hydroxycholesterol results in decreased expression of INHBA protein
CTD PMID:19464342 NCBI chr17:49,091,635...49,111,573
Ensembl chr17:49,095,920...49,108,982
JBrowse link
G Inhbb inhibin subunit beta B increases expression EXP 25-hydroxycholesterol results in increased expression of INHBB mRNA; 25-hydroxycholesterol results in increased expression of INHBB protein CTD PMID:19464342 NCBI chr13:30,530,860...30,536,566
Ensembl chr13:30,530,860...30,537,832
JBrowse link
G Insig1 insulin induced gene 1 decreases expression ISO 25-hydroxycholesterol results in decreased expression of INSIG1 mRNA CTD PMID:19260826 NCBI chr 4:7,315,494...7,323,972
Ensembl chr 4:7,315,495...7,323,952
JBrowse link
G Ldlr low density lipoprotein receptor decreases expression
multiple interactions
ISO 25-hydroxycholesterol results in decreased expression of LDLR mRNA; 25-hydroxycholesterol results in decreased expression of LDLR protein
25-hydroxycholesterol inhibits the reaction [[Resveratrol results in increased activity of and results in increased cleavage of SREBF2 protein] which results in increased expression of LDLR mRNA]; 25-hydroxycholesterol inhibits the reaction [Resveratrol results in increased expression of LDLR mRNA]; LDLR gene mutant form promotes the reaction [[25-hydroxycholesterol co-treated with Cholesterol] results in decreased activity of HMGCR protein]; LDLR gene mutant form results in increased susceptibility to [25-hydroxycholesterol co-treated with Cholesterol]
CTD PMID:12477733 PMID:19260826 PMID:22153697 PMID:27447558 NCBI chr 8:20,270,020...20,292,981
Ensembl chr 8:20,270,041...20,294,580
JBrowse link
G Lpl lipoprotein lipase decreases expression
decreases activity
ISO 25-hydroxycholesterol results in decreased expression of LPL mRNA
25-hydroxycholesterol results in decreased activity of LPL protein
CTD PMID:8567968 NCBI chr16:20,830,055...20,853,855
Ensembl chr16:20,829,465...20,855,249
JBrowse link
G Marchf6 membrane associated ring-CH-type finger 6 increases stability ISO 25-hydroxycholesterol results in increased stability of MARCHF6 protein CTD PMID:30545937 NCBI chr 2:82,455,686...82,532,917
Ensembl chr 2:82,455,689...82,532,910
JBrowse link
G Nos2 nitric oxide synthase 2 increases expression ISO 25-hydroxycholesterol results in increased expression of NOS2 mRNA CTD PMID:12085989 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Nos3 nitric oxide synthase 3 decreases expression ISO 25-hydroxycholesterol results in decreased expression of NOS3 mRNA CTD PMID:19426978 NCBI chr 4:10,793,834...10,814,170
Ensembl chr 4:10,793,834...10,814,166
JBrowse link
G Nr1h3 nuclear receptor subfamily 1, group H, member 3 increases activity
multiple interactions
ISO 25-hydroxycholesterol results in increased activity of NR1H3 protein
[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA; [25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased transport of Cholesterol; [9-deoxy-delta-9-prostaglandin D2 binds to and results in increased activity of PPARG protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]; [9-deoxy-delta-9-prostaglandin D2 binds to and results in increased activity of PPARG protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased transport of Cholesterol]; [Bezafibrate binds to and results in increased activity of PPARA protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]; [Bezafibrate binds to and results in increased activity of PPARA protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased transport of Cholesterol]; SULT2B1 protein inhibits the reaction [25-hydroxycholesterol results in increased activity of NR1H3 protein]
CTD PMID:9603267 PMID:12595494 PMID:27052460 NCBI chr 3:77,158,808...77,168,907
Ensembl chr 3:77,158,808...77,168,722
JBrowse link
G Nr5a1 nuclear receptor subfamily 5, group A, member 1 increases activity
multiple interactions
ISO 25-hydroxycholesterol results in increased activity of NR5A1 protein
25-hydroxycholesterol promotes the reaction [NR5A1 protein results in increased expression of STAR protein]
CTD PMID:9144161 PMID:9804848 NCBI chr 3:22,464,786...22,486,328
Ensembl chr 3:22,465,502...22,486,328
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions ISO [Bezafibrate binds to and results in increased activity of PPARA protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]; [Bezafibrate binds to and results in increased activity of PPARA protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased transport of Cholesterol] CTD PMID:12595494 NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO [9-deoxy-delta-9-prostaglandin D2 binds to and results in increased activity of PPARG protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased expression of ABCA1 mRNA]; [9-deoxy-delta-9-prostaglandin D2 binds to and results in increased activity of PPARG protein] promotes the reaction [[25-hydroxycholesterol binds to and results in increased activity of NR1H3 protein] which results in increased transport of Cholesterol] CTD PMID:12595494 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Rora RAR-related orphan receptor A affects binding ISO 25-hydroxycholesterol binds to RORA protein CTD PMID:31195007 NCBI chr 8:69,301,635...70,034,741
Ensembl chr 8:69,301,733...70,025,931
JBrowse link
G Rorc RAR-related orphan receptor C affects binding
multiple interactions
ISO 25-hydroxycholesterol binds to RORC protein
bisphenol A analog inhibits the reaction [25-hydroxycholesterol binds to RORC protein]; TO-901317 inhibits the reaction [25-hydroxycholesterol binds to RORC protein]
CTD PMID:22659100 PMID:31195007 NCBI chr 2:182,009,707...182,034,910
Ensembl chr 2:182,009,286...182,034,907
JBrowse link
G Scd stearoyl-CoA desaturase decreases expression ISO 25-hydroxycholesterol results in decreased expression of SCD protein CTD PMID:27447558 NCBI chr 1:243,269,745...243,282,878
Ensembl chr 1:243,269,747...243,282,562
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 increases expression
multiple interactions
ISO 25-hydroxycholesterol results in increased expression of SREBF1 protein
[25-hydroxycholesterol co-treated with Cholesterol] results in decreased cleavage of SREBF1 protein
CTD PMID:19260826 PMID:27324795 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Srebf2 sterol regulatory element binding transcription factor 2 decreases activity
multiple interactions
ISO 25-hydroxycholesterol results in decreased activity of SREBF2 protein
25-hydroxycholesterol inhibits the reaction [[Resveratrol results in increased activity of and results in increased cleavage of SREBF2 protein] which results in increased expression of LDLR mRNA]; 25-hydroxycholesterol inhibits the reaction [Resveratrol results in increased activity of and results in increased cleavage of SREBF2 protein]; 25-hydroxycholesterol inhibits the reaction [Resveratrol results in increased expression of SREBF2 protein modified form]; [25-hydroxycholesterol co-treated with Cholesterol] results in decreased cleavage of SREBF2 protein; Clozapine inhibits the reaction [25-hydroxycholesterol results in decreased activity of SREBF2 protein]
CTD PMID:17052361 PMID:22153697 PMID:27324795 NCBI chr 7:113,663,202...113,720,850
Ensembl chr 7:113,663,202...113,720,848
JBrowse link
G Star steroidogenic acute regulatory protein multiple interactions ISO 25-hydroxycholesterol promotes the reaction [NR5A1 protein results in increased expression of STAR protein] CTD PMID:9804848 NCBI chr16:66,267,094...66,274,368
Ensembl chr16:66,264,807...66,271,672
JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions EXP 25-hydroxycholesterol inhibits the reaction [IL6 protein results in increased phosphorylation of STAT3 protein] CTD PMID:27052460 NCBI chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057
JBrowse link
G Sult2b1 sulfotransferase family 2B member 1 multiple interactions ISO SULT2B1 protein inhibits the reaction [25-hydroxycholesterol results in increased activity of NR1H3 protein]
SULT2B1 protein inhibits the reaction [3,5-diethoxycarbonyl-1,4-dihydrocollidine results in increased abundance of 25-hydroxycholesterol]
CTD PMID:27052460 NCBI chr 1:96,200,155...96,261,295
Ensembl chr 1:96,200,156...96,261,295
JBrowse link
G Tnfsf15 TNF superfamily member 15 increases expression ISO 25-hydroxycholesterol results in increased expression of TNFSF15 mRNA CTD PMID:19426978 NCBI chr 5:77,140,099...77,156,142
Ensembl chr 5:77,139,878...77,156,228
JBrowse link
G Vcam1 vascular cell adhesion molecule 1 increases expression ISO 25-hydroxycholesterol results in increased expression of VCAM1 mRNA CTD PMID:19426978 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958
JBrowse link

Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 20059
    role 20009
      biological role 20008
        biochemical role 19630
          metabolite 19611
            eukaryotic metabolite 19318
              algal metabolite 14147
                cholesterol 335
                  25-hydroxycholesterol 43
Path 2
Term Annotations click to browse term
  CHEBI ontology 20059
    subatomic particle 20056
      composite particle 20056
        hadron 20056
          baryon 20056
            nucleon 20056
              atomic nucleus 20056
                atom 20056
                  main group element atom 19956
                    p-block element atom 19956
                      carbon group element atom 19882
                        carbon atom 19873
                          organic molecular entity 19873
                            organic molecule 19819
                              organic cyclic compound 19581
                                organic polycyclic compound 16968
                                  steroid 13379
                                    hydroxy steroid 13008
                                      3-hydroxy steroid 10395
                                        3beta-hydroxy steroid 2023
                                          3beta-hydroxy-Delta(5)-steroid 1854
                                            cholesterol 335
                                              oxysterol 106
                                                25-hydroxycholesterol 43
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