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: norethisterone
Accession: CHEBI:7627
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Definition: A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.
Synonyms: exact_synonym: (17alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one; 17-ethynyl-17beta-hydroxyestr-4-en-3-one
related_synonym: (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one; 17-alpha-ethynyl-17-hydroxy-4-estren-3-one; 17-alpha-ethynyl-19-norandrost-4-en-17-beta-ol-3-one; 17-alpha-ethynyl-19-nortestosterone; 17-alpha-ethynyl-4-estren-17-ol-3-one; 17-beta-hydroxy-19-norpregn-4-en-20-yn-3-one; 17-hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one; 17-hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one; 17alpha-ethinyl-19-nortestosterone; 17alpha-ethinylestra-4-en-17beta-ol-3-one; 17alpha-ethynyl-17-hydroxy-4-estren-3-one; 17alpha-ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one; 17alpha-ethynyl-19-nor-4-androsten-17beta-ol-3-one; 17alpha-ethynyl-19-norandrost-4-en-17beta-ol-3-one; 17alpha-ethynyl-19-nortestosterone; 17alpha-ethynyl-4-estren-17-ol-3-one; 17beta-hydroxy-19-norpregn-4-en-20-yn-3-one; 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one; 19-Norethisterone; 19-nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one; 19-nor-17-alpha-ethynylandrosten-17-beta-ol-3-one; 19-nor-17-alpha-ethynyltestosterone; 19-nor-17alpha-ethynylandrosten-17beta-ol-3-one; 19-nor-17alpha-ethynyltestosterone; 19-nor-ethindrone; 4-estren-17alpha-ethynyl-17beta-ol-3-one; Camila; Conludag; Formula=C20H26O2; InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1; InChIKey=VIKNJXKGJWUCNN-XGXHKTLJSA-N; Micronor; Micronovum; Mini-pe; Mini-pill; Norcolut; Norethindrone; Norethisteron; Noriday; Norluten; Norlutin; Primolut-N; SMILES=C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C; Utovlan; norethisteronum; noretisterona
alt_id: CHEBI:44349
xref: Beilstein:1915671; CAS:68-22-4; DrugBank:DB00717; Drug_Central:1962; HMDB:HMDB0014855; KEGG:C05028; KEGG:D00182; LIPID_MAPS_instance:LMST02030097
xref_mesh: MESH:D009640
xref: PDBeChem:NDR; PMID:120838; PMID:21860523; PMID:24019188; Patent:US2744122; Patent:US2849462; Reaxys:1915671; Wikipedia:Norethisterone
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Abcb11
ATP binding cassette subfamily B member 11
decreases activity
ISO
Norethindrone results in decreased activity of ABCB11 protein
CTD
PMID:20829430
NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730
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Abcb1a
ATP binding cassette subfamily B member 1A
increases expression
ISO
Norethindrone results in increased expression of ABCB1 mRNA
CTD
PMID:15290871
NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
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Adipoq
adiponectin, C1Q and collagen domain containing
multiple interactions
ISO
Norethindrone inhibits the reaction [[Dexamethasone co-treated with Rosiglitazone co-treated with 1-Methyl-3-isobutylxanthine co-treated with INS protein] results in increased expression of and results in increased secretion of ADIPOQ protein]
CTD
PMID:29782964
NCBI chr11:77,721,912...77,735,644
Ensembl chr11:77,721,912...77,735,564
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Akr1c1
aldo-keto reductase family 1, member C1
decreases activity
ISO
Norethindrone results in decreased activity of AKR1C1 protein
CTD
PMID:21182831
NCBI chr17:65,810,474...65,837,385
Ensembl chr17:65,810,475...65,837,326
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Akr1c3
aldo-keto reductase family 1, member C3
decreases activity
ISO
Norethindrone results in decreased activity of AKR1C3 protein
CTD
PMID:21182831
NCBI chr17:66,110,970...66,127,867
Ensembl chr17:66,110,963...66,127,873
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Ar
androgen receptor
affects binding multiple interactions
EXP ISO
Norethindrone binds to AR protein Norethindrone binds to and results in decreased activity of AR protein; Norethindrone binds to and results in increased activity of AR protein
CTD
PMID:14565775 PMID:25752796 PMID:33049310
NCBI chr X:63,104,771...63,273,934
Ensembl chr X:63,104,771...63,273,925
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Bglap
bone gamma-carboxyglutamate protein
increases secretion
ISO
Norethindrone results in increased secretion of BGLAP protein
CTD
PMID:8053399
NCBI chr 2:173,838,518...173,839,495
Ensembl chr 2:173,838,518...173,839,495
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Esr1
estrogen receptor 1
increases activity multiple interactions
EXP ISO
Norethindrone results in increased activity of ESR1 protein ESR1 protein affects the reaction [Norethindrone results in increased expression of GREB1 mRNA]; ESR1 protein affects the reaction [Norethindrone results in increased expression of SGK1 mRNA]; Norethindrone binds to and results in increased activity of ESR1 protein
CTD
PMID:11750080 PMID:12504345 PMID:25012808 PMID:25752796 PMID:33049310 PMID:33405908 More...
NCBI chr 1:41,106,335...41,499,104
Ensembl chr 1:41,210,475...41,495,002
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Esr2
estrogen receptor 2
multiple interactions
ISO
Norethindrone binds to and results in increased activity of ESR2 protein
CTD
PMID:25752796 PMID:33049310
NCBI chr 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919
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F10
coagulation factor X
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in increased expression of F10 protein
CTD
PMID:14561536
NCBI chr16:76,468,834...76,488,141
Ensembl chr16:76,468,838...76,488,141
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F7
coagulation factor VII
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in increased expression of F7 protein
CTD
PMID:14561536
NCBI chr16:76,489,775...76,500,636
Ensembl chr16:76,489,717...76,500,610
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Fabp4
fatty acid binding protein 4
multiple interactions
ISO
Norethindrone inhibits the reaction [[Dexamethasone co-treated with Rosiglitazone co-treated with 1-Methyl-3-isobutylxanthine co-treated with INS protein] results in increased expression of FABP4 protein]
CTD
PMID:29782964
NCBI chr 2:91,580,879...91,585,567
Ensembl chr 2:91,580,885...91,585,578
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Fasn
fatty acid synthase
increases activity
ISO
Norethindrone results in increased activity of FASN protein
CTD
PMID:15870863
NCBI chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261
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Fga
fibrinogen alpha chain
multiple interactions
ISO
[Ethinyl Estradiol co-treated with Norethindrone] results in increased expression of [FGA protein binds to FGB protein binds to FGG protein]
CTD
PMID:14561536
NCBI chr 2:168,374,120...168,381,523
Ensembl chr 2:168,374,120...168,381,528
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Fgb
fibrinogen beta chain
multiple interactions
ISO
[Ethinyl Estradiol co-treated with Norethindrone] results in increased expression of [FGA protein binds to FGB protein binds to FGG protein]
CTD
PMID:14561536
NCBI chr 2:168,394,901...168,402,863
Ensembl chr 2:168,394,916...168,405,979
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Fgg
fibrinogen gamma chain
multiple interactions
ISO
[Ethinyl Estradiol co-treated with Norethindrone] results in increased expression of [FGA protein binds to FGB protein binds to FGG protein]
CTD
PMID:14561536
NCBI chr 2:168,354,880...168,362,325
Ensembl chr 2:168,355,013...168,362,322
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Greb1
growth regulating estrogen receptor binding 1
multiple interactions increases expression
ISO
ESR1 protein affects the reaction [Norethindrone results in increased expression of GREB1 mRNA]; Fulvestrant inhibits the reaction [Norethindrone results in increased expression of GREB1 mRNA]
CTD
PMID:33405908
NCBI chr 6:39,440,522...39,562,364
Ensembl chr 6:39,440,504...39,581,633
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H2ax
H2A.X variant histone
increases phosphorylation
ISO
Norethindrone results in increased phosphorylation of H2AX protein
CTD
PMID:15905198
NCBI chr 8:44,671,907...44,673,262
Ensembl chr 8:44,671,786...44,673,239
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Ins2
insulin 2
multiple interactions
ISO
Norethindrone inhibits the reaction [[Dexamethasone co-treated with Rosiglitazone co-treated with 1-Methyl-3-isobutylxanthine co-treated with INS protein] results in increased expression of and results in increased secretion of ADIPOQ protein]; Norethindrone inhibits the reaction [[Dexamethasone co-treated with Rosiglitazone co-treated with 1-Methyl-3-isobutylxanthine co-treated with INS protein] results in increased expression of FABP4 protein]
CTD
PMID:29782964
NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
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Mapt
microtubule-associated protein tau
decreases expression
ISO
Norethindrone results in decreased expression of MAPT protein
CTD
PMID:16930453
NCBI chr10:89,138,644...89,236,137
Ensembl chr10:89,138,627...89,236,129
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Mybl1
MYB proto-oncogene like 1
multiple interactions increases expression
ISO
Fulvestrant inhibits the reaction [Norethindrone results in increased expression of MYBL1 mRNA]
CTD
PMID:33405908
NCBI chr 5:9,582,905...9,618,179
Ensembl chr 5:9,582,934...9,618,183
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Nr1i2
nuclear receptor subfamily 1, group I, member 2
multiple interactions
ISO
Norethindrone binds to and results in increased activity of NR1I2 protein
CTD
PMID:33049310
NCBI chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
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Pgr
progesterone receptor
multiple interactions
ISO
Norethindrone binds to and results in increased activity of PGR protein
CTD
PMID:15189034 PMID:25752796
NCBI chr 8:6,072,673...6,131,552
Ensembl chr 8:6,072,673...6,131,344
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Plg
plasminogen
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in increased expression of PLG protein
CTD
PMID:14561536
NCBI chr 1:48,325,186...48,367,643
Ensembl chr 1:48,325,185...48,367,786
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Pparg
peroxisome proliferator-activated receptor gamma
multiple interactions
ISO
Norethindrone binds to and results in increased 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
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Proc
protein C, inactivator of coagulation factors Va and VIIIa
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in increased expression of PROC protein
CTD
PMID:14561536
NCBI chr18:23,764,367...23,774,816
Ensembl chr18:23,764,368...23,775,133
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Serpinc1
serpin family C member 1
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in decreased expression of SERPINC1 protein
CTD
PMID:14561536
NCBI chr13:73,257,208...73,271,476
Ensembl chr13:73,257,179...73,284,293
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Serpine1
serpin family E member 1
multiple interactions
ISO
[Ethinyl Estradiol binds to Norethindrone] which results in decreased expression of SERPINE1 protein
CTD
PMID:14561536
NCBI chr12:19,601,272...19,611,657
Ensembl chr12:19,601,272...19,611,657
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Sgk1
serum/glucocorticoid regulated kinase 1
increases expression multiple interactions
ISO
Norethindrone results in increased expression of SGK1 mRNA ESR1 protein affects the reaction [Norethindrone results in increased expression of SGK1 mRNA]; Fulvestrant inhibits the reaction [Norethindrone results in increased expression of SGK1 mRNA]
CTD
PMID:33405908
NCBI chr 1:22,980,257...23,098,122
Ensembl chr 1:22,980,261...23,098,283
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Slc22a2
solute carrier family 22 member 2
multiple interactions
ISO
Norethindrone inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium]
CTD
PMID:21599003
NCBI chr 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268
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Thra
thyroid hormone receptor alpha
multiple interactions
ISO
Norethindrone binds to and results in decreased activity of THRA protein
CTD
PMID:33049310
NCBI chr10:83,701,885...83,729,408
Ensembl chr10:83,700,755...83,729,936
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Thrb
thyroid hormone receptor beta
multiple interactions
ISO
Norethindrone 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
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Tp53
tumor protein p53
multiple interactions
ISO
Norethindrone results in increased expression of and results in increased activity of TP53 protein
CTD
PMID:15905198
NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
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Vegfa
vascular endothelial growth factor A
increases expression
ISO
Norethindrone results in increased expression of VEGFA mRNA; Norethindrone results in increased expression of VEGFA mRNA alternative form
CTD
PMID:17010073
NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
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