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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:SM-164
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Accession:CHEBI:192710 term browser browse the term
Definition:A potent cell-permeable and bivalent Smac mimetic which binds to XIAP, cIAP-1 and cIAP-2 proteins (Ki = 0.56 nM, 0.31 nM and 1.1 nM, respectively). It induces apoptosis and tumor regression in cancer xenograft models.
Synonyms:exact_synonym: (3S,6S,10aS)-6-{[(2S)-2-(methylamino)propanoyl]amino}-N-[(S)-(1-{4-[4-(4-{4-[(S)-({[(3S,6S,10aS)-6-{[(2S)-2-(methylamino)propanoyl]amino}-5-oxodecahydropyrrolo[1,2-a]azocin-3-yl]carbonyl}amino)(phenyl)methyl]-1H-1,2,3-triazol-1-yl}butyl)phenyl]butyl}-1H-1,2,3-triazol-4-yl)(phenyl)methyl]-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide
 related_synonym: Formula=C62H84N14O6;   InChI=1S/C62H84N14O6/c1-41(63-3)57(77)65-49-27-13-11-25-47-33-35-53(75(47)61(49)81)59(79)67-55(45-21-7-5-8-22-45)51-39-73(71-69-51)37-17-15-19-43-29-31-44(32-30-43)20-16-18-38-74-40-52(70-72-74)56(46-23-9-6-10-24-46)68-60(80)54-36-34-48-26-12-14-28-50(62(82)76(48)54)66-58(78)42(2)64-4/h5-10,21-24,29-32,39-42,47-50,53-56,63-64H,11-20,25-28,33-38H2,1-4H3,(H,65,77)(H,66,78)(H,67,79)(H,68,80)/t41-,42-,47-,48-,49-,50-,53-,54-,55-,56-/m0/s1;   InChIKey=LGYDZXNSSLRFJS-IOQQVAQYSA-N;   SM164;   SMILES=[H][C@]12CC[C@H](N1C(=O)[C@H](CCCC2)NC(=O)[C@H](C)NC)C(=O)N[C@H](C1=CN(CCCCC2=CC=C(CCCCN3C=C(N=N3)[C@@H](NC(=O)[C@@H]3CC[C@]4([H])CCCC[C@H](NC(=O)[C@H](C)NC)C(=O)N34)C3=CC=CC=C3)C=C2)N=N1)C1=CC=CC=C1
 xref: CAS:957135-43-2
 xref_mesh: MESH:C533467
 xref: PMID:17999504;   PMID:19010913;   PMID:21282353;   PMID:21372226;   PMID:21462933;   PMID:21901386;   PMID:22148838;   PMID:23142291;   PMID:23240027;   PMID:23699656;   PMID:31059038;   PMID:32332865;   PMID:35525732



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SM-164 term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bid BH3 interacting domain death agonist multiple interactions ISO [TNF protein co-treated with SM 164] results in increased cleavage of BID protein; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of BID protein] CTD PMID:34523043 NCBI chr 4:154,113,198...154,136,353
Ensembl chr 4:154,113,198...154,134,720
JBrowse link
G Birc2 baculoviral IAP repeat-containing 2 increases degradation
decreases expression
ISO SM 164 results in increased degradation of BIRC2 protein
SM-164 decreases expression of BIRC2 protein in nasopharyngeal carcinoma cells
CTD
RGD
PMID:22241084 PMID:23699656 RGD:155226871 NCBI chr 8:4,968,856...4,989,325
Ensembl chr 8:4,968,842...4,988,732
JBrowse link
G Birc3 baculoviral IAP repeat-containing 3 increases degradation ISO SM 164 results in increased degradation of BIRC3 protein CTD PMID:22241084 NCBI chr 8:5,000,844...5,028,470
Ensembl chr 8:5,000,845...5,015,802
JBrowse link
G Casp3 caspase 3 increases cleavage
multiple interactions
ISO SM 164 results in increased cleavage of CASP3 protein
[TNF protein co-treated with SM 164] results in increased cleavage of CASP3 protein; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of CASP3 protein]
CTD PMID:22241084 PMID:34523043 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp9 caspase 9 multiple interactions ISO [TNF protein co-treated with SM 164] results in increased cleavage of CASP9 protein; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of CASP9 protein] CTD PMID:34523043 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO [SM 164 co-treated with bosutinib] results in decreased expression of CCND1 protein; [SM 164 co-treated with GSK 1363089] results in decreased expression of CCND1 protein CTD PMID:22241084 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602
JBrowse link
G Lrig1 leucine-rich repeats and immunoglobulin-like domains 1 affects response to substance
multiple interactions
ISO LRIG1 protein affects the susceptibility to SM 164
LRIG1 protein promotes the reaction [SM 164 results in increased expression of TNF mRNA]; LRIG1 protein promotes the reaction [SM 164 results in increased expression of TNF protein]
CTD PMID:22241084 NCBI chr 4:127,130,899...127,230,956
Ensembl chr 4:127,130,898...127,231,513
JBrowse link
G Map3k14 mitogen-activated protein kinase kinase kinase 14 increases expression ISO SM 164 results in increased expression of MAP3K14 protein CTD PMID:22241084 NCBI chr10:88,165,349...88,215,558
Ensembl chr10:88,165,351...88,215,523
JBrowse link
G Mlkl mixed lineage kinase domain like pseudokinase multiple interactions ISO [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of MLKL protein
[TNF protein co-treated with SM 164 co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone] results in increased phosphorylation of MLKL protein
CTD PMID:34523043 PMID:34942311 NCBI chr19:39,277,526...39,304,555
Ensembl chr19:39,276,785...39,304,502
JBrowse link
G Nfkb2 nuclear factor kappa B subunit 2 increases metabolic processing ISO SM 164 results in increased metabolism of NFKB2 protein CTD PMID:22241084 NCBI chr 1:245,164,586...245,173,225
Ensembl chr 1:245,165,950...245,173,213
JBrowse link
G Nfkbia NFKB inhibitor alpha increases phosphorylation ISO SM 164 results in increased phosphorylation of NFKBIA protein CTD PMID:22241084 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO [TNF protein co-treated with SM 164] results in increased cleavage of PARP1 protein; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of PARP1 protein] CTD PMID:34523043 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit increases phosphorylation
multiple interactions
ISO SM 164 results in increased phosphorylation of RELA protein
RELA protein promotes the reaction [SM 164 results in increased expression of TNF mRNA]
CTD PMID:22241084 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
JBrowse link
G Ripk1 receptor interacting serine/threonine kinase 1 multiple interactions ISO [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein
[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]
CTD PMID:34942311 NCBI chr17:30,839,639...30,871,824
Ensembl chr17:30,839,650...30,871,824
JBrowse link
G Ripk3 receptor-interacting serine-threonine kinase 3 multiple interactions ISO [TNF protein co-treated with SM 164 co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone] results in increased expression of RIPK3 protein modified form; [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein
[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]
CTD PMID:34523043 PMID:34942311 NCBI chr15:29,283,153...29,292,107
Ensembl chr15:29,283,145...29,292,121
JBrowse link
G Tnf tumor necrosis factor multiple interactions
increases response to substance
increases expression
ISO [benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein; [benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein; [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of MLKL protein; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]]; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]
TNF protein results in increased susceptibility to SM 164
[TNF protein co-treated with SM 164 co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone] results in increased expression of RIPK3 protein modified form; [TNF protein co-treated with SM 164 co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone] results in increased phosphorylation of MLKL protein; [TNF protein co-treated with SM 164] results in increased cleavage of BID protein; [TNF protein co-treated with SM 164] results in increased cleavage of CASP3 protein; [TNF protein co-treated with SM 164] results in increased cleavage of CASP9 protein; [TNF protein co-treated with SM 164] results in increased cleavage of PARP1 protein; [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein; [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of BID protein]; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of CASP3 protein]; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of CASP9 protein]; benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone inhibits the reaction [[TNF protein co-treated with SM 164] results in increased cleavage of PARP1 protein]; Cycloheximide inhibits the reaction [SM 164 results in increased expression of TNF mRNA]; LRIG1 protein promotes the reaction [SM 164 results in increased expression of TNF mRNA]; LRIG1 protein promotes the reaction [SM 164 results in increased expression of TNF protein]; RELA protein promotes the reaction [SM 164 results in increased expression of TNF mRNA]
SM 164 results in increased expression of TNF mRNA; SM 164 results in increased expression of TNF protein
CTD PMID:22241084 PMID:34523043 PMID:34942311 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Tnfsf10 TNF superfamily member 10 increases response to substance ISO TNFSF10 protein results in increased susceptibility to SM 164 CTD PMID:22241084 NCBI chr 2:110,199,835...110,227,239
Ensembl chr 2:110,207,916...110,225,135
JBrowse link
G Zfp91 zinc finger protein 91 multiple interactions ISO [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein; [ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein
[ZFP91 protein co-treated with benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of MLKL protein; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]]; necrostatin-1 inhibits the reaction [ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK1 protein]; ZFP91 protein promotes the reaction [[benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone co-treated with SM 164 co-treated with TNF protein] results in increased phosphorylation of RIPK3 protein]
CTD PMID:34942311 NCBI chr 1:209,891,344...209,928,890
Ensembl chr 1:209,891,344...209,927,762
JBrowse link

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  CHEBI ontology 19880
    role 19850
      biological role 19848
        biochemical role 19556
          apoptosis inducer 13663
            SM-164 18
Path 2
Term Annotations click to browse term
  CHEBI ontology 19880
    subatomic particle 19878
      composite particle 19878
        hadron 19878
          baryon 19878
            nucleon 19878
              atomic nucleus 19878
                atom 19878
                  main group element atom 19817
                    p-block element atom 19817
                      carbon group element atom 19757
                        carbon atom 19754
                          organic molecular entity 19754
                            heteroorganic entity 19512
                              organochalcogen compound 19275
                                organooxygen compound 19191
                                  carbon oxoacid 18658
                                    carboxylic acid 18655
                                      carboacyl group 17699
                                        univalent carboacyl group 17699
                                          carbamoyl group 17550
                                            carboxamide 17550
                                              secondary carboxamide 1253
                                                SM-164 18
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