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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:cerivastatin
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Accession:CHEBI:3558 term browser browse the term
Definition:(3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.
Synonyms:exact_synonym: (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
 related_synonym: (3R,5S,6E)-7-(4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acid;   (3R,5S,6E)-7-(4-(p-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acid;   (3R,5S,E)-7-(4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acid;   Formula=C26H34FNO5;   InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1;   InChIKey=SEERZIQQUAZTOL-ANMDKAQQSA-N;   SMILES=COCc1c(nc(C(C)C)c(\\C=C\\[C@@H](O)C[C@@H](O)CC(O)=O)c1-c1ccc(F)cc1)C(C)C;   cerivastatin acid
 alt_id: CHEBI:503465;   MESH:C086276
 xref: Beilstein:8366578;   CAS:145599-86-6;   DrugBank:DB00439;   Drug_Central:577;   KEGG:C07966;   KEGG:D07661
 xref_mesh: MESH:C086276
 xref: PMID:17560788;   PMID:18155906;   Wikipedia:Cerivastatin
 cyclic_relationship: is_conjugate_acid_of CHEBI:406059


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cerivastatin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 multiple interactions
decreases activity		 ISO cerivastatin inhibits the reaction [ABCB11 protein affects the import of Taurocholic Acid]; cerivastatin inhibits the reaction [ABCB11 protein results in increased transport of Taurocholic Acid]
cerivastatin results in decreased activity of ABCB11 protein		 CTD PMID:15901796 PMID:24014644 NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730 		JBrowse link
G Abcb1a ATP binding cassette subfamily B member 1A affects export ISO ABCB1 protein affects the export of cerivastatin CTD PMID:15901800 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 affects export ISO ABCC2 protein affects the export of cerivastatin CTD PMID:15901800 NCBI chr 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238 		JBrowse link
G Abcg2 ATP binding cassette subfamily G member 2 affects export ISO ABCG2 protein affects the export of cerivastatin CTD PMID:15901800 NCBI chr 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409 		JBrowse link
G Bmp2 bone morphogenetic protein 2 increases secretion ISO cerivastatin results in increased secretion of BMP2 protein CTD PMID:16470222 NCBI chr 3:120,812,660...120,822,579
Ensembl chr 3:120,812,882...120,821,397 		JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions		 ISO cerivastatin results in increased activity of CASP3 protein
geranylgeranyl pyrophosphate inhibits the reaction [cerivastatin results in increased activity of CASP3 protein]; Mevalonic Acid inhibits the reaction [cerivastatin results in increased activity of CASP3 protein]		 CTD PMID:15705602 PMID:16470222 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 increases activity ISO cerivastatin results in increased activity of CASP8 protein CTD PMID:15705602 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 ISO cerivastatin results in increased activity of CASP9 protein CTD PMID:15705602 PMID:16470222 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions
decreases expression		 ISO cerivastatin inhibits the reaction [TNF results in increased expression of CCL2 mRNA]; cerivastatin results in decreased expression of and results in decreased secretion of CCL2 protein; Mevalonic Acid inhibits the reaction [cerivastatin inhibits the reaction [TNF results in increased expression of CCL2 mRNA]]
cerivastatin results in decreased expression of CCL2 mRNA		 CTD PMID:12117737 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 increases expression ISO cerivastatin results in increased expression of CYP2B6 mRNA CTD PMID:15802384 NCBI chr 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143 		JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 affects response to substance
increases metabolic processing		 ISO CYP2C8 gene mutant form affects the susceptibility to cerivastatin
CYP2C8 protein results in increased metabolism of cerivastatin		 CTD PMID:12464242 PMID:15365880 PMID:15716363
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases metabolic processing ISO CYP3A4 protein results in increased metabolism of cerivastatin CTD PMID:15365880 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Diablo diablo, IAP-binding mitochondrial protein increases localization ISO cerivastatin results in increased localization of DIABLO protein CTD PMID:15705602 NCBI chr12:33,055,784...33,070,400
Ensembl chr12:33,055,263...33,070,387 		JBrowse link
G Entpd1 ectonucleoside triphosphate diphosphohydrolase 1 multiple interactions ISO cerivastatin inhibits the reaction [F2 protein results in decreased expression of ENTPD1 protein] CTD PMID:12067895 NCBI chr 1:239,425,515...239,552,323
Ensembl chr 1:239,425,430...239,552,317 		JBrowse link
G F2 coagulation factor II multiple interactions ISO cerivastatin inhibits the reaction [F2 protein results in decreased expression of ENTPD1 protein] CTD PMID:12067895 NCBI chr 3:77,596,196...77,609,486
Ensembl chr 3:77,596,198...77,609,486 		JBrowse link
G Fgf2 fibroblast growth factor 2 decreases expression EXP cerivastatin results in decreased expression of FGF2 mRNA; cerivastatin results in decreased expression of FGF2 protein CTD PMID:11479256 NCBI chr 2:120,236,328...120,290,673
Ensembl chr 2:120,236,328...120,291,221 		JBrowse link
G Icam1 intercellular adhesion molecule 1 multiple interactions ISO cerivastatin inhibits the reaction [TNF results in increased expression of ICAM1] CTD PMID:12615677 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438 		JBrowse link
G Il1b interleukin 1 beta decreases expression EXP cerivastatin results in decreased expression of IL1B CTD PMID:12878482 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 multiple interactions
decreases expression		 ISO
EXP		 cerivastatin inhibits the reaction [TNF results in increased expression of IL6 mRNA]; cerivastatin results in decreased expression of and results in decreased secretion of IL6 protein; Mevalonic Acid inhibits the reaction [cerivastatin inhibits the reaction [TNF results in increased expression of IL6 mRNA]]
cerivastatin results in decreased expression of IL6
cerivastatin results in decreased expression of IL6 mRNA		 CTD PMID:11479256 PMID:12117737 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Itgal integrin subunit alpha L multiple interactions ISO cerivastatin inhibits the reaction [TNF results in increased expression of ITGAL] CTD PMID:12615677 NCBI chr 1:181,918,183...181,955,735
Ensembl chr 1:181,918,183...181,955,732 		JBrowse link
G Itgb2 integrin subunit beta 2 multiple interactions ISO cerivastatin inhibits the reaction [TNF results in increased expression of ITGB2] CTD PMID:12615677 NCBI chr20:11,061,394...11,097,656
Ensembl chr20:11,061,430...11,097,600 		JBrowse link
G Mb myoglobin increases secretion EXP cerivastatin results in increased secretion of MB protein CTD PMID:19628585 NCBI chr 7:108,759,903...108,767,134
Ensembl chr 7:108,759,904...108,767,383 		JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 increases activity ISO cerivastatin results in increased activity of NR1I2 protein CTD PMID:15802384 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 decreases activity
increases activity		 ISO
EXP		 cerivastatin results in decreased activity of NR1I3 protein alternative form
cerivastatin results in increased activity of NR1I3 protein		 CTD PMID:15802384 PMID:21778469 NCBI chr13:83,632,940...83,638,193
Ensembl chr13:83,632,899...83,637,906 		JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions ISO cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]; Cholesterol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; Farnesol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; geranylgeraniol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; Mevalonic Acid inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; SREBF1 protein inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]] CTD PMID:11779144 NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346 		JBrowse link
G Rab4a RAB4A, member RAS oncogene family decreases prenylation
affects expression		 EXP cerivastatin results in decreased prenylation of RAB4 protein
cerivastatin affects the expression of RAB4A protein		 CTD PMID:16239165 NCBI chr19:51,795,613...51,822,706
Ensembl chr19:51,795,613...51,822,703 		JBrowse link
G Rap1a RAP1A, member of RAS oncogene family multiple interactions
decreases geranoylation		 ISO Mevalonic Acid inhibits the reaction [cerivastatin results in decreased geranoylation of RAP1A protein] CTD PMID:25578243 NCBI chr 2:193,208,631...193,286,513
Ensembl chr 2:193,208,635...193,286,501 		JBrowse link
G Rhoa ras homolog family member A decreases localization
multiple interactions		 ISO cerivastatin results in decreased localization of RHOA protein
cerivastatin results in increased localization of and results in decreased prenylation of RHOA protein		 CTD PMID:15705602 PMID:16470222 NCBI chr 8:108,991,926...109,025,746
Ensembl chr 8:108,991,954...109,025,746 		JBrowse link
G Rxra retinoid X receptor alpha multiple interactions ISO cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]; Cholesterol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; Farnesol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; geranylgeraniol inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; Mevalonic Acid inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]]; SREBF1 protein inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]] CTD PMID:11779144 NCBI chr 3:10,989,832...11,076,366
Ensembl chr 3:10,989,832...11,073,712 		JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO SREBF1 protein inhibits the reaction [cerivastatin promotes the reaction [Bezafibrate results in increased activity of [PPARA protein binds to RXRA protein]]] CTD PMID:11779144 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO cerivastatin inhibits the reaction [TNF results in increased expression of CCL2 mRNA]; cerivastatin inhibits the reaction [TNF results in increased expression of CXCL8 mRNA]; cerivastatin inhibits the reaction [TNF results in increased expression of ICAM1]; cerivastatin inhibits the reaction [TNF results in increased expression of IL6 mRNA]; cerivastatin inhibits the reaction [TNF results in increased expression of ITGAL]; cerivastatin inhibits the reaction [TNF results in increased expression of ITGB2]; Mevalonic Acid inhibits the reaction [cerivastatin inhibits the reaction [TNF results in increased expression of CCL2 mRNA]]; Mevalonic Acid inhibits the reaction [cerivastatin inhibits the reaction [TNF results in increased expression of CXCL8 mRNA]]; Mevalonic Acid inhibits the reaction [cerivastatin inhibits the reaction [TNF results in increased expression of IL6 mRNA]] CTD PMID:12117737 PMID:12615677 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tnni2 troponin I2, fast skeletal type increases secretion EXP cerivastatin results in increased secretion of TNNI2 protein CTD PMID:19628585 NCBI chr 1:197,595,012...197,597,554
Ensembl chr 1:197,594,813...197,597,560 		JBrowse link
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Term Annotations click to browse term
  CHEBI ontology 19795
    chemical entity 19795
      atom 19794
        nonmetal atom 19681
          nitrogen atom 18762
            nitrogen molecular entity 18762
              organonitrogen compound 18540
                organonitrogen heterocyclic compound 17659
                  pyridines 9157
                    cerivastatin 32
Path 2
Term Annotations click to browse term
  CHEBI ontology 19795
    subatomic particle 19794
      composite particle 19794
        hadron 19794
          baryon 19794
            nucleon 19794
              atomic nucleus 19794
                atom 19794
                  main group element atom 19693
                    p-block element atom 19693
                      carbon group element atom 19614
                        carbon atom 19604
                          organic molecular entity 19604
                            organic group 18713
                              organic divalent group 18697
                                organodiyl group 18697
                                  carbonyl group 18646
                                    carbonyl compound 18646
                                      carboxylic acid 18341
                                        hydroxy carboxylic acid 3656
                                          hydroxy monocarboxylic acid 3656
                                            dihydroxy monocarboxylic acid 257
                                              cerivastatin 32
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