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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 1:252,537,614...252,550,394
Ensembl chr 1:252,537,615...252,550,394
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 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
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 7:121,480,723...121,482,781
Ensembl chr 7:121,480,723...121,482,772
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 chr13:89,053,457...89,242,531
Ensembl chr13:89,055,983...89,242,443
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
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 chr20:20,576,341...20,591,510
Ensembl chr20:20,576,377...20,591,549
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 chr10:88,490,798...88,497,357
Ensembl chr10:88,490,798...88,497,356
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 5:49,307,584...49,333,064
Ensembl chr 5:49,311,030...49,333,056
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 PMID:17558434 PMID:17558435 PMID:17572696 PMID:18247131 PMID:18664590 PMID:21702498 PMID:21871882 PMID:27194477 PMID:30733293 NCBI chr 5:154,242,010...154,268,126
Ensembl chr 5:154,260,062...154,268,126
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 7:70,578,564...70,585,074
Ensembl chr 7:70,580,198...70,585,084
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 chr10:86,367,596...86,391,728
Ensembl chr10:86,367,596...86,391,728
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 9:78,900,111...78,969,018
Ensembl chr 9:78,900,103...78,969,078
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 chr17:72,419,752...72,452,043
Ensembl chr17:72,429,618...72,450,681
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 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762
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 7:61,337,383...61,341,419
Ensembl chr 7:61,337,381...61,341,419
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 chr13:47,738,933...47,743,392
Ensembl chr13:47,739,526...47,743,392
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 chr10:30,034,447...30,048,774
Ensembl chr10:30,038,709...30,048,085
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 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
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 2:123,847,150...123,851,854
Ensembl chr 2:123,847,150...123,851,854
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 chr10:38,963,979...38,969,531
Ensembl chr10:38,963,979...38,969,531
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 chr10:39,066,716...39,069,587
Ensembl chr10:39,066,716...39,069,587
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 chr10:39,109,530...39,116,532
Ensembl chr10:39,109,522...39,116,531
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 1:89,345,325...89,360,905
Ensembl chr 1:89,345,429...89,360,733
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 chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
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 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
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 chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347
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 chr10:35,333,859...35,374,364
Ensembl chr10:35,333,859...35,374,355
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 chr20:2,003,871...2,014,284
Ensembl chr20:2,004,052...2,014,286
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 chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
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 1:194,767,484...194,769,519
Ensembl chr 1:194,767,474...194,769,524
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 4:147,532,040...147,592,769
Ensembl chr 4:147,532,042...147,592,699
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 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 2:219,071,193...219,090,931
Ensembl chr 2:219,071,193...219,097,619
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 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
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 chr14:85,753,736...85,758,820
Ensembl chr14:85,753,760...85,758,145
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 19773
    role 19719
      biological role 19719
        pharmacological role 18831
          antagonist 16284
            cannabinoid receptor antagonist 451
              CB2 receptor antagonist 37
                SR 144528 37
Path 2
Term Annotations click to browse term
  CHEBI ontology 19773
    subatomic particle 19772
      composite particle 19772
        hadron 19772
          baryon 19772
            nucleon 19772
              atomic nucleus 19772
                atom 19772
                  main group element atom 19662
                    p-block element atom 19662
                      carbon group element atom 19579
                        carbon atom 19569
                          organic molecular entity 19569
                            organic group 18613
                              organic divalent group 18604
                                organodiyl group 18604
                                  carbonyl group 18521
                                    carbonyl compound 18521
                                      carboxylic acid 18196
                                        carboacyl group 17418
                                          univalent carboacyl group 17418
                                            carbamoyl group 17218
                                              carboxamide 17218
                                                secondary carboxamide 303
                                                  SR 144528 37
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