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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 4:88,765,441...88,890,268
Ensembl chr 4:88,832,178...88,890,621
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 6:7,935,771...7,961,207
Ensembl chr 6:7,935,771...7,961,207
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 6:7,961,413...7,980,708
Ensembl chr 6:7,961,413...7,980,708
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 chr17:69,761,126...69,778,021
Ensembl chr17:69,761,118...69,778,021
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 4:65,110,706...65,143,930
Ensembl chr 4:65,110,746...65,143,941
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 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, PMID:21273442, PMID:23562765, PMID:28973534 NCBI chr  X:67,656,253...67,828,998
Ensembl chr  X:67,656,253...67,829,026
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 5:50,362,491...50,393,368
Ensembl chr 5:50,381,244...50,393,367
JBrowse link
G Crebbp CREB binding protein increases activity ISO Androstenedione results in increased activity of CREBBP protein CTD PMID:16467117 NCBI chr10:11,590,994...11,721,039
Ensembl chr10:11,595,044...11,721,039
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 8:62,798,317...62,809,848
Ensembl chr 8:62,779,875...62,809,893
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, PMID:21427057, PMID:29100959 NCBI chr 1:266,422,127...266,429,947
Ensembl chr 1:266,422,132...266,428,239
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, PMID:16569475, PMID:21273442, PMID:21439382, PMID:22120136, PMID:26162595, PMID:31330226 NCBI chr 8:58,744,849...58,772,408
Ensembl chr 8:58,744,849...58,772,408
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 7:99,142,431...99,183,540
Ensembl chr 7:99,142,450...99,181,783
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 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Dhrs11 dehydrogenase/reductase 11 increases reduction ISO DHRS11 protein results in increased reduction of Androstenedione CTD PMID:30926317 NCBI chr10:72,144,042...72,153,496
Ensembl chr10:72,144,042...72,153,375
JBrowse link
G Dhrs3 dehydrogenase/reductase 3 increases metabolic processing ISO DHRS3 protein results in increased metabolism of Androstenedione CTD PMID:25451588 NCBI chr 5:162,809,090...162,843,385
Ensembl chr 5:162,808,646...162,843,383
JBrowse link
G Dhrs7 dehydrogenase/reductase 7 increases reduction ISO DHRS7 protein results in increased reduction of Androstenedione CTD PMID:24246760 NCBI chr 6:95,522,577...95,541,393
Ensembl chr 6:95,522,577...95,541,393
JBrowse link
G Faslg Fas ligand decreases expression EXP Androstenedione results in decreased expression of FASLG mRNA CTD PMID:21439382 NCBI chr13:79,696,811...79,717,581
Ensembl chr13:79,698,445...79,705,705
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 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
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 8:85,640,081...85,645,621 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 3:82,924,699...83,048,465
Ensembl chr 3:82,924,687...83,048,435
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 chr19:50,246,404...50,317,892
Ensembl chr19:50,246,402...50,317,891
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 chr17:1,579,319...1,610,745
Ensembl chr17:1,579,319...1,610,745
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
G Lep leptin multiple interactions EXP LEP protein inhibits the reaction [CGA protein results in increased secretion of Androstenedione] CTD PMID:14657608 NCBI chr 4:56,337,695...56,351,818
Ensembl chr 4:56,337,695...56,351,818
JBrowse link
G Lhb luteinizing hormone subunit beta increases abundance ISO LHB protein results in increased abundance of Androstenedione CTD PMID:23433069 NCBI chr 1:101,409,992...101,413,725
Ensembl chr 1:101,410,019...101,413,724
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 5:165,263,813...165,373,967
Ensembl chr 5:165,263,800...165,373,967
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 6:28,677,563...28,931,844
Ensembl chr 6:28,677,540...28,931,843
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 5:5,466,544...5,696,540
Ensembl chr 5:5,616,483...5,694,598
JBrowse link
G Ncoa3 nuclear receptor coactivator 3 increases activity ISO Androstenedione results in increased activity of NCOA3 protein CTD PMID:16467117 NCBI chr 3:162,692,176...162,788,582
Ensembl chr 3:162,692,185...162,787,548
JBrowse link
G Nos2 nitric oxide synthase 2 increases expression EXP Androstenedione results in increased expression of NOS2 mRNA CTD PMID:21439382 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
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 chr13:89,585,072...89,591,278
Ensembl chr13:89,586,283...89,591,277
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 chr13:53,750,470...53,870,288
Ensembl chr13:53,750,473...53,870,428
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 chr10:34,149,717...34,155,198
Ensembl chr10:34,149,717...34,155,198
Ensembl chr12:34,149,717...34,155,198
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 chr10:88,686,207...88,712,313
Ensembl chr10:88,686,207...88,754,829
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    chemical entity 19816
      group 19728
        organic group 18537
          3-oxo-Delta(4)-steroid group 7939
            3-oxo-Delta(4) steroid 7939
              androst-4-ene-3,17-dione 35
                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 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      ketone 16173
                                        oxo steroid 9283
                                          3-oxo steroid 8811
                                            3-oxo-Delta(4) steroid 7939
                                              androst-4-ene-3,17-dione 35
                                                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

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.