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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:4-hydroxy-17beta-estradiol
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Accession:CHEBI:62845 term browser browse the term
Definition:A 4-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 4.
Synonyms:exact_synonym: estra-1,3,5(10)-triene-3,14,17beta-triol
 related_synonym: 3,4,17beta-estriol;   3,4,17beta-trihydroxy-1,3,5[10]-estratriene;   4-Hydroxyestradiol-17beta;   4-OH-Estradiol;   4-hydroxyestradiol;   4OHE2;   Formula=C18H24O3;   InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1;   InChIKey=QOZFCKXEVSGWGS-ZHIYBZGJSA-N;   SMILES=[H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc1c(O)c(O)ccc21
 alt_id: CHEBI:34424
 xref: CAS:5976-61-4;   HMDB:HMDB0005896;   KEGG:C14209;   LIPID_MAPS_instance:LMST02010028
 xref_mesh: MESH:C014036
 xref: PMID:10077490;   PMID:11258977;   PMID:11812141;   PMID:11961123;   PMID:12093619;   PMID:12493568;   PMID:16112522;   PMID:17173372;   PMID:18379081;   PMID:20540524;   PMID:20708024;   PMID:9554872;   Reaxys:2219366


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4-hydroxy-17beta-estradiol term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akt1 AKT serine/threonine kinase 1 multiple interactions
increases phosphorylation		 ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [4-hydroxyestradiol results in increased phosphorylation of AKT1 protein]; wortmannin inhibits the reaction [4-hydroxyestradiol results in increased phosphorylation of AKT1 protein] CTD PMID:15050414 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Alpg alkaline phosphatase, germ cell increases activity ISO 4-hydroxyestradiol results in increased activity of ALPG protein CTD PMID:15993745 NCBI chr 9:87,748,721...87,761,500
Ensembl chr 9:87,753,648...87,757,836 		JBrowse link
G Ar androgen receptor affects binding EXP 4-hydroxyestradiol binds to AR protein CTD PMID:14565775 NCBI chr  X:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925 		JBrowse link
G Ccnd1 cyclin D1 increases expression
multiple interactions		 ISO 4-hydroxyestradiol results in increased expression of CCND1 mRNA; 4-hydroxyestradiol results in increased expression of CCND1 protein
alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of CCND1 mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of CCND1 protein]		 CTD PMID:23685341 PMID:31364906 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Cdh1 cadherin 1 multiple interactions
decreases expression		 ISO alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in decreased expression of CDH1 mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in decreased expression of CDH1 protein]
4-hydroxyestradiol results in decreased expression of CDH1 mRNA; 4-hydroxyestradiol results in decreased expression of CDH1 protein		 CTD PMID:31364906 NCBI chr19:34,492,371...34,561,775
Ensembl chr19:34,492,371...34,561,775 		JBrowse link
G Comt catechol-O-methyltransferase affects metabolic processing
increases methylation
multiple interactions		 ISO COMT protein affects the metabolism of 4-hydroxyestradiol
COMT protein results in increased methylation of 4-hydroxyestradiol
daidzein inhibits the reaction [COMT protein results in increased methylation of 4-hydroxyestradiol]; Estradiol inhibits the reaction [COMT protein results in increased methylation of 4-hydroxyestradiol]; Genistein inhibits the reaction [COMT protein results in increased methylation of 4-hydroxyestradiol]		 CTD PMID:15377160 PMID:18192686 NCBI chr11:82,568,052...82,587,642
Ensembl chr11:82,568,025...82,587,642 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions ISO 4-hydroxyestradiol promotes the reaction [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein] CTD PMID:12093619 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 affects chemical synthesis
multiple interactions
increases chemical synthesis		 ISO CYP1B1 protein affects the chemical synthesis of 4-hydroxyestradiol
[CYP1B1 protein results in increased oxidation of Estradiol] which results in increased chemical synthesis of 4-hydroxyestradiol; CYP1B1 protein affects the metabolism of [4-hydroxyestradiol co-treated with Glutathione]; Resveratrol inhibits the reaction [CYP1B1 protein affects the chemical synthesis of 4-hydroxyestradiol]
CYP1B1 gene polymorphism results in increased chemical synthesis of 4-hydroxyestradiol		 CTD PMID:14679015 PMID:15142886 PMID:18187806 PMID:32781018 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917 		JBrowse link
G Esr1 estrogen receptor 1 affects binding
multiple interactions
increases expression		 ISO 4-hydroxyestradiol binds to ESR1 protein
4-hydroxyestradiol inhibits the reaction [16 alpha-iodoestradiol binds to ESR1 protein]; [4-hydroxyestradiol results in increased activity of ESR1 protein] promotes the reaction [ESR1 protein binds to TFF1 promoter]
4-hydroxyestradiol results in increased expression of ESR1 protein		 CTD PMID:9048584 PMID:15993745 PMID:20540524 PMID:23685341 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 affects binding
multiple interactions
decreases expression		 ISO
EXP		 4-hydroxyestradiol binds to ESR2 protein
4-hydroxyestradiol inhibits the reaction [16 alpha-iodoestradiol binds to ESR2 protein]
4-hydroxyestradiol results in decreased expression of ESR2 protein
4-OH-estradiol binds to Esr2 protein		 CTD
RGD		 PMID:9048584 PMID:15993745 PMID:23685341 PMID:9048584 RGD:8694130 NCBI chr 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919 		JBrowse link
G Foxo1 forkhead box O1 decreases expression ISO 4-hydroxyestradiol results in decreased expression of FOXO1 protein CTD PMID:23685341 NCBI chr 2:136,312,168...136,390,603
Ensembl chr 2:136,312,168...136,387,790 		JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha multiple interactions
increases expression		 ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [4-hydroxyestradiol results in increased expression of HIF1A protein]; Sirolimus inhibits the reaction [4-hydroxyestradiol results in increased expression of HIF1A protein]; wortmannin inhibits the reaction [4-hydroxyestradiol results in increased expression of HIF1A protein] CTD PMID:15050414 NCBI chr 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261 		JBrowse link
G Igf1r insulin-like growth factor 1 receptor increases expression ISO 4-hydroxyestradiol results in increased expression of IGF1R protein CTD PMID:23685341 NCBI chr 1:121,549,831...121,838,548
Ensembl chr 1:121,550,743...121,831,777 		JBrowse link
G Igfbp1 insulin-like growth factor binding protein 1 increases expression
multiple interactions		 ISO 4-hydroxyestradiol results in increased expression of IGFBP1 mRNA
4-hydroxyestradiol promotes the reaction [[Medroxyprogesterone Acetate co-treated with Cyclic AMP] results in increased expression of IGFBP1 mRNA]		 CTD PMID:32781018 NCBI chr14:82,047,415...82,052,482
Ensembl chr14:82,047,415...82,052,482 		JBrowse link
G Lep leptin increases abundance ISO LEP protein results in increased abundance of 4-hydroxyestradiol CTD PMID:24631339 NCBI chr 4:57,661,127...57,675,262
Ensembl chr 4:57,661,131...57,675,262 		JBrowse link
G Ltf lactotransferrin increases expression ISO 4-hydroxyestradiol results in increased expression of LTF mRNA CTD PMID:9371753 PMID:9607801 NCBI chr 8:110,999,948...111,022,795
Ensembl chr 8:110,999,948...111,022,795 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO 4-hydroxyestradiol results in increased phosphorylation of and results in increased activity of MAPK1 protein; U 0126 inhibits the reaction [4-hydroxyestradiol results in increased phosphorylation of MAPK1 protein] CTD PMID:15901486 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO 4-hydroxyestradiol results in increased phosphorylation of and results in increased activity of MAPK3 protein; U 0126 inhibits the reaction [4-hydroxyestradiol results in increased phosphorylation of MAPK3 protein] CTD PMID:15901486 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions
increases expression		 ISO alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MMP2 mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MMP2 protein]
4-hydroxyestradiol results in increased expression of MMP2 mRNA; 4-hydroxyestradiol results in increased expression of MMP2 protein		 CTD PMID:31364906 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions
increases expression		 ISO alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MMP9 mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MMP9 protein]
4-hydroxyestradiol results in increased expression of MMP9 mRNA; 4-hydroxyestradiol results in increased expression of MMP9 protein		 CTD PMID:31364906 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Mt-atp6 mitochondrially encoded ATP synthase membrane subunit 6 increases expression ISO 4-hydroxyestradiol results in increased expression of ATP6 mRNA CTD PMID:9886577 NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
NCBI chr MT:7,919...8,599
Ensembl chr MT:7,919...8,599 		JBrowse link
G Mt-co3 mitochondrially encoded cytochrome c oxidase III increases expression ISO 4-hydroxyestradiol results in increased expression of COX3 mRNA CTD PMID:9886577 NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
NCBI chr MT:8,599...9,382
Ensembl chr MT:8,599...9,382 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor increases expression
multiple interactions		 ISO 4-hydroxyestradiol results in increased expression of MYC mRNA; 4-hydroxyestradiol results in increased expression of MYC protein
alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MYC mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of MYC protein]		 CTD PMID:23685341 PMID:31364906 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 multiple interactions ISO 4-hydroxyestradiol results in increased activity of [NFKB1 protein binds to RELA protein] CTD PMID:15901486 NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Pgr progesterone receptor increases expression ISO 4-hydroxyestradiol results in increased expression of PGR mRNA CTD PMID:9607801 NCBI chr 8:6,072,673...6,131,552
Ensembl chr 8:6,072,673...6,131,344 		JBrowse link
G Prl prolactin increases expression
multiple interactions		 ISO 4-hydroxyestradiol results in increased expression of PRL mRNA
4-hydroxyestradiol promotes the reaction [[Medroxyprogesterone Acetate co-treated with Cyclic AMP] results in increased expression of PRL mRNA]		 CTD PMID:32781018 NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO [2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA; Acetylcysteine inhibits the reaction [[2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA]; Acetylcysteine inhibits the reaction [Estradiol promotes the reaction [[2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA]]; BAY 11-7085 inhibits the reaction [[2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA]; BAY 11-7085 inhibits the reaction [Estradiol promotes the reaction [[2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA]]; Estradiol promotes the reaction [[2-hydroxyestradiol co-treated with 4-hydroxyestradiol] results in increased expression of PTGS2 mRNA] CTD PMID:18480072 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO 4-hydroxyestradiol results in increased activity of [NFKB1 protein binds to RELA protein] CTD PMID:15901486 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Shbg sex hormone binding globulin increases expression ISO 4-hydroxyestradiol results in increased expression of SHBG mRNA; 4-hydroxyestradiol results in increased expression of SHBG protein CTD PMID:21793624 NCBI chr10:54,332,939...54,350,409
Ensembl chr10:54,332,941...54,351,057 		JBrowse link
G Sphk1 sphingosine kinase 1 increases expression ISO 4-hydroxyestradiol results in increased expression of SPHK1 mRNA CTD PMID:29654831 NCBI chr10:101,758,567...101,764,240
Ensembl chr10:101,758,711...101,764,240 		JBrowse link
G Tff1 trefoil factor 1 multiple interactions ISO [4-hydroxyestradiol results in increased activity of ESR1 protein] promotes the reaction [ESR1 protein binds to TFF1 promoter] CTD PMID:20540524 NCBI chr20:9,235,736...9,239,597
Ensembl chr20:9,235,736...9,239,597 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions
increases expression		 ISO 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [4-hydroxyestradiol results in increased expression of VEGFA protein]; Sirolimus inhibits the reaction [4-hydroxyestradiol results in increased expression of VEGFA protein]; wortmannin inhibits the reaction [4-hydroxyestradiol results in increased expression of VEGFA protein] CTD PMID:15050414 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Vim vimentin multiple interactions
increases expression		 ISO alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of VIM mRNA]; alpha-naphthoflavone inhibits the reaction [4-hydroxyestradiol results in increased expression of VIM protein]
4-hydroxyestradiol results in increased expression of VIM mRNA; 4-hydroxyestradiol results in increased expression of VIM protein		 CTD PMID:31364906 NCBI chr17:76,668,701...76,677,186
Ensembl chr17:76,668,647...76,677,187 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19867
    role 19837
      biological role 19835
        biochemical role 19552
          metabolite 19539
            4-hydroxy-17beta-estradiol 33
              4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) 0
              4-hydroxy-17beta-estradiol 4-O-(beta-D-glucuronide) 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19867
    subatomic particle 19865
      composite particle 19865
        hadron 19865
          baryon 19865
            nucleon 19865
              atomic nucleus 19865
                atom 19865
                  main group element atom 19803
                    p-block element atom 19803
                      carbon group element atom 19744
                        carbon atom 19740
                          organic molecular entity 19740
                            organic molecule 19692
                              organic cyclic compound 19482
                                organic polycyclic compound 17292
                                  steroid 14713
                                    hydroxy steroid 14463
                                      3-hydroxy steroid 12808
                                        phenolic steroid 11313
                                          estradiol 11309
                                            17beta-estradiol 11309
                                              4-hydroxy-17beta-estradiol 33
                                                4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) 0
                                                4-hydroxy-17beta-estradiol 4-O-(beta-D-glucuronide) 0
paths to the root