Page last updated: 2024-11-13

smm-189

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

SMM-189: a cannabinoid 2 receptor inverse agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID25030040
CHEMBL ID460545
SCHEMBL ID1206345
MeSH IDM000609846

Synonyms (10)

Synonym
bdbm50248604
(3'',5''-dichloro-2,6-dihydroxybiphenyl-4-yl)(phenyl)methanone
CHEMBL460545 ,
SCHEMBL1206345
smm-189
DTXSID201019032
[4-(35-dichlorophenyl)-35-dihydroxy-phenyl]-phenyl-methanone
1054451-07-8
[4-(3,5-dichlorophenyl)-3,5-dihydroxyphenyl]-phenylmethanone
AKOS040749535
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)Ki3.19430.00010.50779.6000AID1241320; AID1719525; AID414286
Cannabinoid receptor 2 Homo sapiens (human)Ki0.08180.00000.415610.0000AID1241321; AID1719526; AID414287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.15430.00030.15173.2800AID1241325; AID1719530; AID1719542
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1719528Inverse agonist activity at human recombinant cannabinoid CB1 receptor expressed in HEK cells transfected with CNG assessed as increase in cAMP level measured up to 1 hr by ACTOne membrane potential dye based assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1719525Displacement of [3H]-CP55940 from human recombinant cannabinoid CB1 receptor expressed in HEK cell membranes incubated for 1.5 hrs by liquid scintillation counting method2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1719540Inverse agonist activity at cannabinoid CB1 receptor in human U2OS cells assessed as induction of beta-arrestin recruitment using CCF4/AM as substrate preincubated for 5 hrs followed by substrate addition and measured after 2 hrs by Tango assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1719527Selectivity ratio of Ki for displacement of [3H]-CP55940 from human recombinant cannabinoid CB1 receptor expressed in HEK cell membranes to displacement of [3H]-CP55940 from human recombinant cannabinoid CB2 receptor expressed in HEK cell membranes2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1241326Inverse agonist activity at CB2 receptor (unknown origin) expressed in HEK cells assessed as increase in cAMP production at 5 x 10'-6 to 5 x 10'-10 M measured at 50 mins by ACTOne dye-based fluorescence assay in presence of forskolin and Ro 20-1724 relati2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID1719543Inverse agonist activity at cannabinoid CB2 receptor in human U2OS cells assessed as emission ratio using CCF4/AM as substrate preincubated for 5 hrs followed by substrate addition and measured after 2 hrs by Tango assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1241324Inverse agonist activity at CB1 receptor (unknown origin) expressed in HEK cells assessed as increase in cAMP production at 5 x 10'-6 to 5 x 10'-10 M measured at 50 mins by ACTOne dye-based fluorescence assay in presence of forskolin and Ro 20-1724 relati2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID414287Binding affinity to human CB2 receptor transfected in HEK293 cells2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID1719530Inverse agonist activity at human recombinant cannabinoid CB2 receptor expressed in HEK cells transfected with CNG assessed as increase in cAMP level measured up to 1 hr by ACTOne membrane potential dye based assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1241327Non-competitive antagonist activity at CB2 receptor (unknown origin) expressed in HEK cells incubated in dark condition for 30 mins prior to CP55940 addition measured at 50 mins by Schild plot analysis2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID1719542Inverse agonist activity at cannabinoid CB2 receptor in human U2OS cells assessed as induction of beta-arrestin recruitment using CCF4/AM as substrate preincubated for 5 hrs followed by substrate addition and measured after 2 hrs by Tango assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1719541Inverse agonist activity at cannabinoid CB1 receptor in human U2OS cells assessed as emission ratio using CCF4/AM as substrate preincubated for 5 hrs followed by substrate addition and measured after 2 hrs by Tango assay2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1241322Selectivity ratio of Ki for CB1 receptor (unknown origin) to Ki for CB2 receptor (unknown origin)2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID414286Binding affinity to human CB1 receptor transfected in HEK293 cells2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID1719531Inverse agonist activity at human recombinant cannabinoid CB2 receptor expressed in HEK cells transfected with CNG assessed as increase in cAMP level measured up to 1 hr by ACTOne membrane potential dye based assay relative to control2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1241321Displacement of [3H]-CP55940 from CB2 receptor (unknown origin) expressed in CHO cell membranes after 90 mins by liquid scintillation counting analysis2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID1241320Displacement of [3H]-CP55940 from CB1 receptor (unknown origin) expressed in CHO cell membranes after 90 mins by liquid scintillation counting analysis2015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID1241323Inverse agonist activity at CB1 receptor (unknown origin) expressed in HEK cells assessed as increase in cAMP production measured at 50 mins by ACTOne dye-based fluorescence assay in presence of forskolin and Ro 20-17242015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
AID1719529Inverse agonist activity at human recombinant cannabinoid CB1 receptor expressed in HEK cells transfected with CNG assessed as increase in cAMP level measured up to 1 hr by ACTOne membrane potential dye based assay relative to control2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID1719526Displacement of [3H]-CP55940 from human recombinant cannabinoid CB2 receptor expressed in HEK cell membranes incubated for 1.5 hrs by liquid scintillation counting method2021Bioorganic & medicinal chemistry, 03-01, Volume: 33Synthesis and biological evaluation of a ring analogs of the selective CB2 inverse agonist SMM-189.
AID414288Selectivity ratio of Ki for human CB1 receptor to Ki for human CB2 receptor2009Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6
Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands.
AID1241325Inverse agonist activity at CB2 receptor (unknown origin) expressed in HEK cells assessed as increase in cAMP production measured at 50 mins by ACTOne dye-based fluorescence assay in presence of forskolin and Ro 20-17242015Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17
Synthesis and biological evaluation of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.04

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.04 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]