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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:androst-4-ene-3,17-dione
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Accession:CHEBI:16422 term browser browse the term
Definition:A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.
Synonyms:related_synonym: 4-ANDROSTENE-3-17-DIONE;   Androstenedione;   Delta(4)-androsten-3,17-dione;   Delta(4)-androstene-3,17-dione;   Formula=C19H26O2;   InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1;   InChIKey=AEMFNILZOJDQLW-QAGGRKNESA-N;   SMILES=[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]
 alt_id: CHEBI:11964;   CHEBI:13830;   CHEBI:20322;   CHEBI:2709;   CHEBI:40930
 xref: Beilstein:2059239;   CAS:63-05-8;   DrugBank:DB01536;   Drug_Central:215;   Gmelin:961672;   HMDB:HMDB0000053;   KEGG:C00280;   KEGG:D00051;   KNApSAcK:C00003644;   LIPID_MAPS_instance:LMST02020007
 xref_mesh: MESH:D000735
 xref: MetaCyc:ANDROST4ENE;   PDBeChem:ASD;   PMID:24423344;   PMID:24740546;   Reaxys:2059239;   Wikipedia:Androstenedione


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androst-4-ene-3,17-dione term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcg2 ATP binding cassette subfamily G member 2 multiple interactions
decreases activity
ISO Androstenedione inhibits the reaction [ABCG2 protein results in increased uptake of estrone sulfate]
Androstenedione results in decreased activity of ABCG2 protein
CTD PMID:22581381 NCBI chr 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409
JBrowse link
G Abcg5 ATP binding cassette subfamily G member 5 multiple interactions ISO Androstenedione results in increased activity of [ABCG5 protein binds to ABCG8 protein] CTD PMID:17055487 NCBI chr 6:9,965,118...9,990,563
Ensembl chr 6:9,965,118...9,990,563
JBrowse link
G Abcg8 ATP binding cassette subfamily G member 8 multiple interactions ISO Androstenedione results in increased activity of [ABCG5 protein binds to ABCG8 protein] CTD PMID:17055487 NCBI chr 6:9,945,629...9,964,912
Ensembl chr 6:9,945,629...9,964,912
JBrowse link
G Akr1c3 aldo-keto reductase family 1, member C3 increases metabolic processing
increases reduction
multiple interactions
ISO AKR1C3 protein results in increased metabolism of Androstenedione
AKR1C3 protein results in increased reduction of Androstenedione
[AKR1C3 protein results in increased metabolism of Androstenedione] which results in increased chemical synthesis of Dihydrotestosterone; [AKR1C3 protein results in increased metabolism of Androstenedione] which results in increased chemical synthesis of Testosterone; [AKR1C3 protein results in increased reduction of Androstenedione] which results in increased chemical synthesis of Testosterone; Indomethacin analog inhibits the reaction [AKR1C3 protein results in increased reduction of Androstenedione]; Indomethacin inhibits the reaction [AKR1C3 protein results in increased reduction of Androstenedione]; N-(4-chlorobenzoyl)melatonin inhibits the reaction [AKR1C3 protein results in increased reduction of Androstenedione]
CTD PMID:17950253 PMID:19010312 PMID:20036328 NCBI chr17:66,110,970...66,127,867
Ensembl chr17:66,110,963...66,127,873
JBrowse link
G Akr1d1 aldo-keto reductase family 1, member D1 increases reduction
multiple interactions
ISO AKR1D1 protein results in increased reduction of Androstenedione
[AKR1D1 protein alternative form results in increased reduction of Androstenedione] which results in increased chemical synthesis of androstane-3,17-dione; [AKR1D1 protein alternative form results in increased reduction of Androstenedione] which results in increased chemical synthesis of Etiocholanolone; [AKR1D1 protein results in increased reduction of Androstenedione] which results in increased chemical synthesis of androstane-3,17-dione; [AKR1D1 protein results in increased reduction of Androstenedione] which results in increased chemical synthesis of Etiocholanolone
AKR1D1 protein alternative form results in increased reduction of Androstenedione; AKR1D1 protein results in increased reduction of Androstenedione
CTD PMID:30928400 NCBI chr 4:66,154,246...66,187,505
Ensembl chr 4:66,154,248...66,186,372
JBrowse link
G Ar androgen receptor affects binding
multiple interactions
EXP
ISO
Androstenedione binds to AR protein
Androstenedione binds to and results in increased activity of AR protein
Androstenedione binds to and affects the activity of AR protein; Androstenedione binds to and results in increased activity of AR protein; Androstenedione inhibits the reaction [[Dihydrotestosterone binds to and results in increased activity of AR protein] which results in increased expression of KLK3 protein]; NCOA2 protein promotes the reaction [Androstenedione binds to and results in increased activity of AR protein]
AR mutant form inhibits the reaction [Androstenedione results in increased expression of NR5A2 mRNA]
CTD PMID:12730620 PMID:14565775 PMID:15336702 PMID:17804755 PMID:19833195 More... NCBI chr  X:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925
JBrowse link
G Cga glycoprotein hormones, alpha polypeptide increases secretion
multiple interactions
EXP CGA protein results in increased secretion of Androstenedione
LEP protein inhibits the reaction [CGA protein results in increased secretion of Androstenedione]; Sodium Glutamate inhibits the reaction [CGA protein results in increased secretion of Androstenedione]
CTD PMID:14657608 NCBI chr 5:49,486,915...49,499,192
Ensembl chr 5:49,487,068...49,499,191
JBrowse link
G Crebbp CREB binding protein increases activity ISO Androstenedione results in increased activity of CREBBP protein CTD PMID:16467117 NCBI chr10:11,335,551...11,461,888
Ensembl chr10:11,335,953...11,461,888
JBrowse link
G Cyp11a1 cytochrome P450, family 11, subfamily a, polypeptide 1 multiple interactions
increases expression
EXP [Diethylstilbestrol results in decreased expression of CYP11A1 protein] which results in decreased abundance of Androstenedione; bicalutamide inhibits the reaction [Androstenedione results in increased expression of CYP11A1 protein]; Finasteride promotes the reaction [Androstenedione results in increased expression of CYP11A1 mRNA]; formestane promotes the reaction [Androstenedione results in increased expression of CYP11A1 mRNA] CTD PMID:21273442 PMID:23873838 NCBI chr 8:58,422,807...58,434,342
Ensembl chr 8:58,404,669...58,434,338
JBrowse link
G Cyp17a1 cytochrome P450, family 17, subfamily a, polypeptide 1 decreases expression
affects chemical synthesis
multiple interactions
affects abundance
ISO Androstenedione results in decreased expression of CYP17A1 mRNA
CYP17A1 protein affects the chemical synthesis of Androstenedione
[CYP17A1 protein results in increased metabolism of 17-alpha-Hydroxyprogesterone] which results in increased chemical synthesis of Androstenedione; Duloxetine Hydrochloride inhibits the reaction [[CYP17A1 protein results in increased metabolism of 17-alpha-Hydroxyprogesterone] which results in increased chemical synthesis of Androstenedione]; TNF protein inhibits the reaction [CYP17A1 protein affects the chemical synthesis of Androstenedione]; Venlafaxine Hydrochloride inhibits the reaction [[CYP17A1 protein results in increased metabolism of 17-alpha-Hydroxyprogesterone] which results in increased chemical synthesis of Androstenedione]
CYP17A1 protein affects the abundance of Androstenedione
CTD PMID:14522586 PMID:15555913 PMID:15562394 PMID:15625562 PMID:16030167 More... NCBI chr 1:245,535,462...245,543,148
Ensembl chr 1:245,535,462...245,541,573
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 affects metabolic processing
increases metabolic processing
decreases expression
multiple interactions
increases expression
ISO
EXP
CYP19A1 protein affects the metabolism of Androstenedione
CYP19A1 protein results in increased metabolism of Androstenedione
Androstenedione results in decreased expression of CYP19A1 mRNA
[Androstenedione results in decreased expression of CYP19A1 mRNA] which results in decreased abundance of Estradiol; bicalutamide inhibits the reaction [Androstenedione results in increased expression of CYP19A1 protein]; Finasteride promotes the reaction [Androstenedione results in increased expression of CYP19A1 mRNA]; formestane promotes the reaction [Androstenedione results in increased expression of CYP19A1 mRNA]
2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane inhibits the reaction [CYP19A1 protein results in increased metabolism of Androstenedione]; [Fluconazole results in decreased activity of CYP19A1 protein] which results in decreased metabolism of Androstenedione; [Ketoconazole results in increased activity of CYP19A1 protein] which results in increased metabolism of Androstenedione; Atrazine promotes the reaction [CYP19A1 protein results in increased metabolism of Androstenedione]; bisphenol A affects the reaction [CYP19A1 protein results in increased metabolism of Androstenedione]; CYP19A1 protein binds to and results in increased metabolism of Androstenedione; Methoxychlor affects the reaction [CYP19A1 protein results in increased metabolism of Androstenedione]; Methyltestosterone inhibits the reaction [CYP19A1 protein affects the metabolism of Androstenedione]; Nandrolone inhibits the reaction [CYP19A1 protein affects the metabolism of Androstenedione]; Testosterone inhibits the reaction [CYP19A1 protein affects the metabolism of Androstenedione]; TNF protein promotes the reaction [CYP19A1 protein affects the metabolism of Androstenedione]; trestolone inhibits the reaction [CYP19A1 protein affects the metabolism of Androstenedione]; tributyltin inhibits the reaction [CYP19A1 protein binds to and results in increased metabolism of Androstenedione]
CTD PMID:11522339 PMID:12628686 PMID:16030167 PMID:16033851 PMID:16054388 More... NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 decreases expression
increases expression
ISO Androstenedione results in decreased expression of CYP2B10 mRNA
Androstenedione results in increased expression of CYP2B10 mRNA
CTD PMID:7771797 PMID:11075820 NCBI chr 1:81,518,387...81,544,999
Ensembl chr 1:81,518,408...81,542,052
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 increases expression ISO Androstenedione results in increased expression of CYP2B9 mRNA CTD PMID:7771797 NCBI chr 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions ISO Androstenedione promotes the reaction [CYP3A4 protein results in increased oxidation of 7-benzyloxy-4-trifluoromethylcoumarin] CTD PMID:19299527 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Dhrs11 dehydrogenase/reductase 11 increases reduction ISO DHRS11 protein results in increased reduction of Androstenedione CTD PMID:30926317 NCBI chr10:69,698,214...69,708,294
Ensembl chr10:69,698,214...69,708,295
JBrowse link
G Dhrs3 dehydrogenase/reductase 3 increases metabolic processing ISO DHRS3 protein results in increased metabolism of Androstenedione CTD PMID:25451588 NCBI chr 5:156,747,939...156,782,420
Ensembl chr 5:156,747,962...156,782,417
JBrowse link
G Dhrs7 dehydrogenase/reductase 7 increases reduction ISO DHRS7 protein results in increased reduction of Androstenedione CTD PMID:24246760 NCBI chr 6:91,332,259...91,347,856
Ensembl chr 6:91,251,323...91,347,892
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions ISO Androstenedione binds to and results in increased activity of ESR1 protein CTD PMID:33049310 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 Androstenedione binds to and results in increased activity of ESR2 protein CTD PMID:33049310 NCBI chr 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919
JBrowse link
G Faslg Fas ligand decreases expression EXP Androstenedione results in decreased expression of FASLG mRNA CTD PMID:21439382 NCBI chr13:74,151,519...74,172,760
Ensembl chr13:74,154,954...74,162,215
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 increases chemical synthesis ISO GSTA1 protein results in increased chemical synthesis of Androstenedione CTD PMID:23650189 NCBI chr 9:23,703,476...23,720,121
Ensembl chr 9:23,703,477...23,720,121
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 decreases metabolic processing ISO GSTA2 protein polymorphism results in decreased metabolism of Androstenedione CTD PMID:15077012 NCBI chr 8:79,184,535...79,196,827
Ensembl chr 8:79,184,322...79,196,798
JBrowse link
G Hsd17b12 hydroxysteroid (17-beta) dehydrogenase 12 increases metabolic processing ISO HSD17B12 protein results in increased metabolism of Androstenedione CTD PMID:17641292 NCBI chr 3:79,990,048...80,113,556
Ensembl chr 3:79,990,056...80,113,617
JBrowse link
G Hsd17b2 hydroxysteroid (17-beta) dehydrogenase 2 increases chemical synthesis ISO HSD17B2 protein results in increased chemical synthesis of Androstenedione CTD PMID:16054388 NCBI chr19:45,753,576...45,825,203
Ensembl chr19:45,753,574...45,825,202
JBrowse link
G Hsd17b3 hydroxysteroid (17-beta) dehydrogenase 3 increases metabolic processing ISO HSD17B3 protein results in increased metabolism of Androstenedione CTD PMID:17071532 NCBI chr17:1,027,229...1,058,554
Ensembl chr17:1,027,229...1,058,554
JBrowse link
G Hsd3b1 hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1 increases chemical synthesis ISO HSD3B1 protein results in increased chemical synthesis of Androstenedione CTD PMID:16054388 NCBI chr 2:186,169,864...186,175,984
Ensembl chr 2:186,169,863...186,175,999
JBrowse link
G Lep leptin multiple interactions EXP LEP protein inhibits the reaction [CGA protein results in increased secretion of Androstenedione] CTD PMID:14657608 NCBI chr 4:57,661,127...57,675,262
Ensembl chr 4:57,661,131...57,675,262
JBrowse link
G Lhb luteinizing hormone subunit beta increases abundance ISO LHB protein results in increased abundance of Androstenedione CTD PMID:23433069 NCBI chr 1:95,898,269...95,901,973
Ensembl chr 1:95,900,984...95,901,972
Ensembl chr 1:95,900,984...95,901,972
JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions
affects activity
ISO [letrozole co-treated with Everolimus] inhibits the reaction [Androstenedione affects the activity of MTOR protein]; Everolimus inhibits the reaction [Androstenedione affects the activity of MTOR protein]; letrozole inhibits the reaction [Androstenedione affects the activity of MTOR protein] CTD PMID:16033851 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Ncoa1 nuclear receptor coactivator 1 multiple interactions ISO 1,4-bis(2-(3,5-dichloropyridyloxy))benzene inhibits the reaction [Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]]; Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]; isopimpinellin inhibits the reaction [Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]] CTD PMID:18692084 NCBI chr 6:27,232,609...27,507,992
Ensembl chr 6:27,232,611...27,475,664
JBrowse link
G Ncoa2 nuclear receptor coactivator 2 multiple interactions ISO NCOA2 protein promotes the reaction [Androstenedione binds to and results in increased activity of AR protein] CTD PMID:15336702 NCBI chr 5:5,835,642...6,069,693
Ensembl chr 5:5,835,706...6,067,451
JBrowse link
G Ncoa3 nuclear receptor coactivator 3 increases activity ISO Androstenedione results in increased activity of NCOA3 protein CTD PMID:16467117 NCBI chr 3:154,738,566...154,821,395
Ensembl chr 3:154,738,581...154,818,594
JBrowse link
G Nos2 nitric oxide synthase 2 increases expression EXP Androstenedione results in increased expression of NOS2 mRNA CTD PMID:21439382 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO Androstenedione binds to and results in increased activity of NR1I2 protein
Androstenedione binds to and affects the activity of NR1I2 protein
CTD PMID:33049310 NCBI chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 multiple interactions
decreases activity
ISO 1,4-bis(2-(3,5-dichloropyridyloxy))benzene inhibits the reaction [Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]]; 1,4-bis(2-(3,5-dichloropyridyloxy))benzene inhibits the reaction [Androstenedione results in decreased activity of NR1I3 protein]; Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]; isopimpinellin inhibits the reaction [Androstenedione inhibits the reaction [NR1I3 protein binds to NCOA1 protein]]; isopimpinellin inhibits the reaction [Androstenedione results in decreased activity of NR1I3 protein] CTD PMID:11075820 PMID:18692084 NCBI chr13:83,632,940...83,638,193
Ensembl chr13:83,632,899...83,637,906
JBrowse link
G Nr5a2 nuclear receptor subfamily 5, group A, member 2 increases expression
multiple interactions
EXP Androstenedione results in increased expression of NR5A2 mRNA
AR mutant form inhibits the reaction [Androstenedione results in increased expression of NR5A2 mRNA]
CTD PMID:21273442 NCBI chr13:48,313,634...48,433,494
Ensembl chr13:48,316,301...48,433,326
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO Androstenedione binds to and results in decreased activity of PPARG protein CTD PMID:33049310 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Rack1 receptor for activated C kinase 1 increases expression ISO Androstenedione results in increased expression of RACK1 mRNA; Androstenedione results in increased expression of RACK1 protein CTD PMID:27239218 NCBI chr10:33,169,415...33,174,896
Ensembl chr10:33,169,169...33,174,975
JBrowse link
G Stat5b signal transducer and activator of transcription 5B increases activity ISO Androstenedione results in increased activity of STAT5B protein CTD PMID:28973534 NCBI chr10:85,704,841...85,775,856
Ensembl chr10:85,705,670...85,775,668
JBrowse link
G Thrb thyroid hormone receptor beta multiple interactions ISO Androstenedione binds to and results in increased activity of THRB protein CTD PMID:33049310 NCBI chr15:7,685,180...8,031,920
Ensembl chr15:7,685,180...7,882,916
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO TNF protein inhibits the reaction [CYP17A1 protein affects the chemical synthesis of Androstenedione]; TNF protein promotes the reaction [CYP19A1 protein affects the metabolism of Androstenedione] CTD PMID:16030167 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19808
    chemical entity 19808
      group 19729
        organic group 18725
          3-oxo-Delta(4)-steroid group 8424
            3-oxo-Delta(4) steroid 8424
              androst-4-ene-3,17-dione 41
                1alpha-hydroxyandrost-4-ene-3,17-dione 0
                3,17-dioxoandrost-4-en-19-al 0
                6beta-hydroxyandrost-4-ene-3,17-dione 0
                9alpha-hydroxyandrost-4-en-3,17-dione 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19808
    subatomic particle 19807
      composite particle 19807
        hadron 19807
          baryon 19807
            nucleon 19807
              atomic nucleus 19807
                atom 19807
                  main group element atom 19704
                    p-block element atom 19704
                      carbon group element atom 19626
                        carbon atom 19616
                          organic molecular entity 19616
                            organic group 18725
                              organic divalent group 18716
                                organodiyl group 18716
                                  carbonyl group 18664
                                    carbonyl compound 18664
                                      ketone 16925
                                        oxo steroid 9719
                                          3-oxo steroid 9282
                                            3-oxo-Delta(4) steroid 8424
                                              androst-4-ene-3,17-dione 41
                                                1alpha-hydroxyandrost-4-ene-3,17-dione 0
                                                3,17-dioxoandrost-4-en-19-al 0
                                                6beta-hydroxyandrost-4-ene-3,17-dione 0
                                                9alpha-hydroxyandrost-4-en-3,17-dione 0
paths to the root