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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:buprenorphine
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Accession:CHEBI:3216 term browser browse the term
Definition:A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.
Synonyms:exact_synonym: (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
 related_synonym: 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol;   2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol;   2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanol;   21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine;   Formula=C29H41NO4;   InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1;   InChIKey=RMRJXGBAOAMLHD-IHFGGWKQSA-N;   SMILES=[H][C@@]1(C[C@]23CC[C@]1(OC)[C@@H]1Oc4c(O)ccc5C[C@H]2N(CC[C@@]31c45)CC1CC1)[C@](C)(O)C(C)(C)C;   buprenorfina;   buprenorphinum
 alt_id: CHEBI:143179;   CHEBI:166254;   CHEBI:453763;   CHEBI:489640;   CHEBI:656608
 xref: Beilstein:6182863;   CAS:52485-79-7;   Chemspider:559124;   DrugBank:DB00921;   Drug_Central:434;   HMDB:HMDB0015057;   KEGG:C08007;   KEGG:D07132
 xref_mesh: MESH:D002047
 xref: MetaCyc:CPD-22086;   PMCID:PMC7711199;   PMID:10649968;   PMID:11303059;   PMID:15181649;   PMID:15781180;   PMID:16642964;   PMID:16650985;   PMID:17887741;   PMID:18997874;   PMID:19402772;   PMID:32925232;   PMID:33378137;   Patent:GB1136214;   Patent:US3433791;   VSDB:1789;   Wikipedia:Buprenorphine


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buprenorphine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bdnf brain-derived neurotrophic factor decreases expression EXP Buprenorphine results in decreased expression of BDNF protein CTD PMID:24321744 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615 		JBrowse link
G Cat catalase decreases activity
multiple interactions		 EXP
ISO		 Buprenorphine results in decreased activity of CAT protein
[2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine co-treated with Buprenorphine] results in increased activity of CAT protein		 CTD PMID:25683329 PMID:32113805 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Creb1 cAMP responsive element binding protein 1 decreases phosphorylation EXP Buprenorphine results in decreased phosphorylation of CREB1 protein CTD PMID:24321744 NCBI chr 9:65,903,511...65,972,562
Ensembl chr 9:65,903,547...65,970,816 		JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 affects metabolic processing ISO CYP2C8 protein affects the metabolism of Buprenorphine CTD PMID:16010532
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 increases metabolic processing
decreases activity		 ISO CYP2D6 protein results in increased metabolism of Buprenorphine
Buprenorphine results in decreased activity of CYP2D6 protein		 CTD PMID:12756210 NCBI chr 7:113,882,584...113,891,754
Ensembl chr 7:113,881,618...113,891,759 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 affects metabolic processing
decreases activity
increases metabolic processing
decreases alkylation		 ISO CYP3A4 protein affects the metabolism of Buprenorphine
Buprenorphine results in decreased activity of CYP3A4 protein
CYP3A4 protein results in increased metabolism of Buprenorphine
CYP3A4 protein results in decreased alkylation of Buprenorphine		 CTD PMID:12756210 PMID:15966752 PMID:16010532 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Gpt glutamic--pyruvic transaminase increases activity EXP Buprenorphine results in increased activity of GPT protein CTD PMID:25683329 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494 		JBrowse link
G Il2 interleukin 2 decreases expression ISO Buprenorphine results in decreased expression of IL2 mRNA CTD PMID:23965172 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566 		JBrowse link
G Il4 interleukin 4 increases expression ISO Buprenorphine results in increased expression of IL4 mRNA CTD PMID:23965172 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO Buprenorphine results in increased phosphorylation of MAPK1 protein CTD PMID:23965172 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 increases phosphorylation ISO Buprenorphine results in increased phosphorylation of MAPK3 protein CTD PMID:23965172 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Ntrk2 neurotrophic receptor tyrosine kinase 2 decreases phosphorylation EXP Buprenorphine results in decreased phosphorylation of NTRK2 protein CTD PMID:24321744 NCBI chr17:5,558,992...5,870,299
Ensembl chr17:5,559,043...5,869,136 		JBrowse link
G Oprd1 opioid receptor, delta 1 affects binding
multiple interactions		 EXP
ISO		 Buprenorphine binds to OPRD1 protein
Buprenorphine inhibits the reaction [Enkephalin, D-Penicillamine (2,5)- analog binds to OPRD1 protein]		 CTD PMID:7562497 PMID:21866885 NCBI chr 5:144,306,188...144,340,960
Ensembl chr 5:144,306,188...144,340,960 		JBrowse link
G Oprk1 opioid receptor, kappa 1 affects binding
multiple interactions		 EXP
ISO		 Buprenorphine binds to OPRK1 protein
Buprenorphine inhibits the reaction [U 69593 binds to OPRK1 protein]		 CTD PMID:7562497 PMID:21866885 NCBI chr 5:13,860,016...13,877,823
Ensembl chr 5:13,860,021...13,877,823 		JBrowse link
G Oprl1 opioid related nociceptin receptor 1 multiple interactions ISO Buprenorphine binds to and results in increased activity of OPRL1 protein CTD PMID:10998549 NCBI chr 3:168,831,934...168,839,920
Ensembl chr 3:168,834,003...168,839,920 		JBrowse link
G Oprm1 opioid receptor, mu 1 multiple interactions
affects binding		 ISO
EXP		 Buprenorphine binds to and affects the activity of OPRM1 protein; Buprenorphine binds to and results in increased activity of OPRM1 protein; Buprenorphine inhibits the reaction [Enkephalin, Ala(2)-MePhe(4)-Gly(5)- binds to OPRM1 protein]
Buprenorphine binds to OPRM1 protein		 CTD PMID:7562497 PMID:16010532 PMID:21866885 NCBI chr 1:43,160,057...43,413,409
Ensembl chr 1:43,160,057...43,413,409 		JBrowse link
G Prkaca protein kinase cAMP-activated catalytic subunit alpha decreases activity EXP Buprenorphine results in decreased activity of PRKACA protein CTD PMID:24321744 NCBI chr19:24,155,081...24,178,430
Ensembl chr19:24,155,090...24,178,430 		JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases glucuronidation ISO UGT1A1 protein results in increased glucuronidation of Buprenorphine CTD PMID:12756209 NCBI chr 9:88,801,344...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19898
    role 19868
      biological role 19866
        pharmacological role 19098
          analgesic 14787
            opioid analgesic 743
              buprenorphine 18
                buprenorphine hydrochlorie 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19898
    subatomic particle 19896
      composite particle 19896
        hadron 19896
          baryon 19896
            nucleon 19896
              atomic nucleus 19896
                atom 19896
                  main group element atom 19835
                    p-block element atom 19835
                      carbon group element atom 19774
                        carbon atom 19771
                          organic molecular entity 19771
                            heteroorganic entity 19528
                              organonitrogen compound 18853
                                alkaloid 8020
                                  isoquinoline alkaloid 1203
                                    morphinane alkaloid 700
                                      buprenorphine 18
                                        buprenorphine hydrochlorie 0
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