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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:SR 144528
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Accession:CHEBI:146245 term browser browse the term
Definition:A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-(4-chloro-3-methylphenyl)-1-(4-methylbenzyl)-1H-pyrazole-3-carboxylic acid with the amino group of (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-amine. A potent and selective cannabinoid receptor type 2 (CB2 receptor) inverse agonist (Ki = 0.6 nM).
Synonyms:exact_synonym: 5-(4-chloro-3-methylphenyl)-1-(4-methylbenzyl)-N-[(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl]-1H-pyrazole-3-carboxamide
 related_synonym: (1S-endo)-5-(4-chloro-3-methylphenyl)-1-((4-methylphenyl)methyl)-N-(1,3,3-trimethylbicyclo(2.2.1)hept-2-yl)-1H-pyrazole-3-carboxamide;   5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide;   Formula=C29H34ClN3O;   InChI=1S/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1;   InChIKey=SUGVYNSRNKFXQM-XRHWURSXSA-N;   SMILES=[C@H]1(C([C@@H]2CC[C@]1(C2)C)(C)C)NC(=O)C3=NN(C(=C3)C4=CC(=C(Cl)C=C4)C)CC5=CC=C(C=C5)C;   SR144528
 xref: CAS:192703-06-3
 xref_mesh: MESH:C110630
 xref: PMID:10400664;   PMID:10448934;   PMID:10462063;   PMID:10915832;   PMID:12514329;   PMID:16224548;   PMID:18804501;   PMID:19338772;   PMID:20089805;   PMID:20132133;   PMID:23855811;   PMID:31236475;   PMID:9454810;   PMID:9918562;   Wikipedia:SR-144\,528



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SR 144528 term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acta2 actin alpha 2, smooth muscle multiple interactions ISO SR 144528 inhibits the reaction [celastrol inhibits the reaction [Folic Acid results in increased expression of ACTA2 protein]] CTD PMID:29789558 NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased phosphorylation of AKT1 protein]; SR 144528 inhibits the reaction [Dronabinol results in increased phosphorylation of AKT1 protein]; SR 144528 inhibits the reaction [methanandamide results in increased phosphorylation of AKT1 protein] CTD PMID:12834810 PMID:30733293 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Atf4 activating transcription factor 4 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [Dronabinol results in increased expression of ATF4 mRNA] CTD PMID:31054322 NCBI chr 7:111,804,135...111,806,457
Ensembl chr 7:111,804,183...111,806,446
JBrowse link
G Atf6 activating transcription factor 6 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [Dronabinol results in increased expression of ATF6 mRNA] CTD PMID:31054322 NCBI chr13:82,927,579...83,106,381
Ensembl chr13:82,930,034...83,107,177
JBrowse link
G Casp3 caspase 3 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased activity of CASP3 protein] CTD PMID:16818634 PMID:16818650 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CCL2 mRNA]]; SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CCL2 protein]] CTD PMID:10218491 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Cdk1 cyclin-dependent kinase 1 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased expression of CDK1 protein] CTD PMID:16818634 NCBI chr20:19,266,226...19,281,417
Ensembl chr20:19,266,248...19,281,408
JBrowse link
G Cnp 2',3'-cyclic nucleotide 3' phosphodiesterase multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of CNP protein] CTD PMID:32956517 NCBI chr10:85,511,164...85,517,723
Ensembl chr10:85,511,160...85,517,720
JBrowse link
G Cnr1 cannabinoid receptor 1 multiple interactions ISO SR 144528 inhibits the reaction [[anandamide binds to and results in increased activity of CNR1 protein] inhibits the reaction [Lipopolysaccharides results in increased transport of Nitric Oxide]] CTD PMID:11891798 NCBI chr 5:48,408,543...48,436,099
Ensembl chr 5:48,408,574...48,435,099
JBrowse link
G Cnr2 cannabinoid receptor 2 affects binding
multiple interactions
ISO
EXP
SR 144528 binds to CNR2 protein
SR 144528 binds to and results in decreased activity of CNR2 protein
[SR 144528 binds to and results in decreased activity of CNR2 protein] which results in decreased susceptibility to (3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone; [SR 144528 binds to and results in decreased activity of CNR2 protein] which results in decreased susceptibility to palmidrol analog; SR 144528 binds to and results in decreased activity of CNR2 protein; SR 144528 inhibits the reaction [[3-(1,1-dimethyl-heptyl)-1-9-dihydroxy-benzo(c)chromen-6-one binds to and results in increased activity of CNR2 protein] which results in decreased susceptibility to Paclitaxel]; SR 144528 inhibits the reaction [[AM 1241 binds to and results in increased activity of CNR2 protein] which results in decreased susceptibility to Paclitaxel]; SR 144528 inhibits the reaction [CNR2 protein affects the susceptibility to Dronabinol]
[SR 144528 binds to and results in increased activity of CNR2 protein] inhibits the reaction [glyceryl 2-arachidonate results in increased expression of CXCL8 protein]; SR 144528 binds to and results in decreased activity of CNR2 protein; SR 144528 inhibits the reaction [[3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol binds to and results in increased activity of CNR2 protein] inhibits the reaction [Colforsin results in increased abundance of Cyclic AMP]]; SR 144528 inhibits the reaction [[virodhamine binds to and results in increased activity of CNR2 protein] inhibits the reaction [Colforsin results in increased abundance of Cyclic AMP]]; SR 144528 inhibits the reaction [CNR2 protein affects the reaction [glyceryl 2-arachidonate results in increased transport of Calcium]]; SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CCL2 mRNA]]; SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CCL2 protein]]; SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CXCL8 mRNA]]; SR 144528 inhibits the reaction [CNR2 protein promotes the reaction [3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol results in increased expression of CXCL8 protein]]; SR 144528 inhibits the reaction [Dronabinol inhibits the reaction [ERBB2 protein binds to CNR2 protein]]
CTD PMID:10218491 PMID:10617657 PMID:10688601 PMID:12509806 PMID:15115777 More... NCBI chr 5:148,125,222...148,151,548
Ensembl chr 5:148,125,604...148,151,548
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [Dronabinol results in increased expression of DDIT3 mRNA] CTD PMID:31054322 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Erbb2 erb-b2 receptor tyrosine kinase 2 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol inhibits the reaction [ERBB2 protein binds to CNR2 protein]]; SR 144528 inhibits the reaction [Dronabinol inhibits the reaction [ERBB2 protein binds to ERBB2 protein]]; SR 144528 inhibits the reaction [Dronabinol results in decreased expression of and affects the phosphorylation of ERBB2 protein] CTD PMID:30733293 NCBI chr10:83,411,197...83,435,078
Ensembl chr10:83,411,313...83,435,078
JBrowse link
G Fn1 fibronectin 1 multiple interactions ISO SR 144528 inhibits the reaction [celastrol inhibits the reaction [Folic Acid results in increased expression of FN1 protein]] CTD PMID:29789558 NCBI chr 9:73,196,044...73,264,695
Ensembl chr 9:73,196,044...73,264,678
JBrowse link
G Gata3 GATA binding protein 3 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of GATA3 mRNA] CTD PMID:14741435 NCBI chr17:68,643,760...68,666,000
Ensembl chr17:68,643,873...68,665,391
JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [Dronabinol results in increased expression of HSPA5 mRNA] CTD PMID:31054322 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891
JBrowse link
G Ifng interferon gamma multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased expression of IFNG mRNA]; SR 144528 inhibits the reaction [Dronabinol results in decreased expression of IFNG protein] CTD PMID:12446015 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375
JBrowse link
G Il10 interleukin 10 multiple interactions ISO SR 144528 inhibits the reaction [1,1-dimethylbutyl-1-deoxy-Delta(9)-THC promotes the reaction [Lipopolysaccharides results in increased secretion of IL10 protein]] CTD PMID:15821753 NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
JBrowse link
G Il12b interleukin 12B multiple interactions ISO SR 144528 inhibits the reaction [1,1-dimethylbutyl-1-deoxy-Delta(9)-THC inhibits the reaction [Lipopolysaccharides results in increased secretion of IL12B protein]] CTD PMID:15821753 NCBI chr10:28,888,832...28,903,796
Ensembl chr10:28,893,008...28,902,903
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [OMDM-1 cpd inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]]; SR 144528 inhibits the reaction [OMDM-1 cpd inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]] CTD PMID:15748152 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il2 interleukin 2 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased expression of IL2 mRNA] CTD PMID:12446015 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
JBrowse link
G Il4 interleukin 4 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of IL4 mRNA]; SR 144528 inhibits the reaction [Dronabinol results in increased expression of IL4 protein] CTD PMID:12446015 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
JBrowse link
G Il5 interleukin 5 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of IL5 mRNA] CTD PMID:12446015 NCBI chr10:37,874,342...37,877,213
Ensembl chr10:37,874,342...37,877,213
JBrowse link
G Irf1 interferon regulatory factor 1 multiple interactions ISO SR 144528 inhibits the reaction [caryophyllene inhibits the reaction [TNF protein results in increased expression of IRF1 protein]] CTD PMID:28624443 NCBI chr10:37,917,155...37,924,166
Ensembl chr10:37,916,670...37,924,166
JBrowse link
G Mag myelin-associated glycoprotein multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of MAG protein] CTD PMID:32956517 NCBI chr 1:86,148,227...86,163,726
Ensembl chr 1:86,148,228...86,163,656
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased phosphorylation of MAPK1 protein]; SR 144528 inhibits the reaction [Dronabinol results in increased phosphorylation of MAPK1 protein]; SR 144528 inhibits the reaction [methanandamide results in increased phosphorylation of MAPK1 protein] CTD PMID:12834810 PMID:30733293 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 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in decreased phosphorylation of MAPK3 protein]; SR 144528 inhibits the reaction [Dronabinol results in increased phosphorylation of MAPK3 protein]; SR 144528 inhibits the reaction [methanandamide results in increased phosphorylation of MAPK3 protein] CTD PMID:12834810 PMID:30733293 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased phosphorylation of MAPK8 protein] CTD PMID:24184660 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981
JBrowse link
G Mapk9 mitogen-activated protein kinase 9 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased phosphorylation of MAPK9 protein] CTD PMID:24184660 NCBI chr10:34,169,661...34,211,138
Ensembl chr10:34,169,675...34,210,178
JBrowse link
G Mog myelin oligodendrocyte glycoprotein multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of MOG protein] CTD PMID:32956517 NCBI chr20:1,513,137...1,523,473
Ensembl chr20:1,513,239...1,523,474
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [OMDM-1 cpd inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein]] CTD PMID:15748152 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Nupr1 nuclear protein 1, transcriptional regulator multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of NUPR1 mRNA] CTD PMID:16818650 NCBI chr 1:181,213,292...181,215,327 JBrowse link
G Raf1 Raf-1 proto-oncogene, serine/threonine kinase multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased localization of RAF1 protein]; SR 144528 inhibits the reaction [methanandamide results in increased localization of RAF1 protein] CTD PMID:12834810 NCBI chr 4:148,679,534...148,740,265
Ensembl chr 4:148,679,530...148,740,317
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions ISO SR 144528 inhibits the reaction [Dronabinol results in increased expression of TGFB1 protein] CTD PMID:11779138 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO SR 144528 inhibits the reaction [caryophyllene inhibits the reaction [TNF protein results in increased expression of IRF1 protein]]; SR 144528 inhibits the reaction [caryophyllene inhibits the reaction [TNF protein results in increased expression of VCAM1 protein]] CTD PMID:28624443 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Vcam1 vascular cell adhesion molecule 1 multiple interactions ISO SR 144528 inhibits the reaction [caryophyllene inhibits the reaction [TNF protein results in increased expression of VCAM1 protein]] CTD PMID:28624443 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958
JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions ISO SR 144528 inhibits the reaction [(3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone results in decreased expression of and results in decreased secretion of VEGFA protein] CTD PMID:15313899 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
JBrowse link
G Xbp1 X-box binding protein 1 multiple interactions ISO [Rimonabant co-treated with SR 144528] inhibits the reaction [Dronabinol results in increased expression of XBP1 mRNA alternative form] CTD PMID:31054322 NCBI chr14:80,390,629...80,395,713
Ensembl chr14:80,390,643...80,395,693
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 20059
    role 20009
      biological role 20008
        pharmacological role 19070
          antagonist 16360
            cannabinoid receptor antagonist 452
              CB2 receptor antagonist 37
                SR 144528 37
Path 2
Term Annotations click to browse term
  CHEBI ontology 20059
    subatomic particle 20056
      composite particle 20056
        hadron 20056
          baryon 20056
            nucleon 20056
              atomic nucleus 20056
                atom 20056
                  main group element atom 19956
                    p-block element atom 19956
                      carbon group element atom 19882
                        carbon atom 19873
                          organic molecular entity 19873
                            organic group 18943
                              organic divalent group 18928
                                organodiyl group 18928
                                  carbonyl group 18877
                                    carbonyl compound 18877
                                      carboxylic acid 18565
                                        carboacyl group 17658
                                          univalent carboacyl group 17658
                                            carbamoyl group 17492
                                              carboxamide 17492
                                                secondary carboxamide 543
                                                  SR 144528 37
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