Page last updated: 2024-12-10

hu 308

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

Description

HU 308: a specific agonist for CB(2), a peripheral cannabinoid receptor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

HU-308 : A carbobicyclic compound that is bicyclo[3.1.1]hept-2-ene which is substituted by a hydroxymethyl group at position 2, a 2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl group at position 4, and two methyl groups at position 6 (the 1S,4S,5S stereoisomer). A highly selective and effective cannabinoid type-2 agonist and the enantiomer of HU-433. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID11553430
CHEMBL ID2179724
CHEBI ID146244
SCHEMBL ID14440176
MeSH IDM0354888

Synonyms (30)

Synonym
onternabez
hu308
(+)-{(1s,4s,5s)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}methanol
CHEBI:146244
hu 308
hu-308
{(1s,4s,5s)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}methanol
8i5l034d55 ,
onternabez [usan]
ards003
who 11976
ppp-003
unii-8i5l034d55
256934-39-1
bdbm50399157
chembl2179724 ,
4-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol
(1s,4s,5s)-4-(4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene-2-methanol
ard-s003
bicyclo(3.1.1)hept-2-ene-2-methanol, 4-(4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl)-6,6-dimethyl-, (1s,4s,5s)-
(+)-hu-308
onternabez [inn]
SCHEMBL14440176
AKOS024457418
DTXSID801017327
(1s,4s,5s)-4-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol
[(1s,4s,5s)-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methanol
E98722
KO3 ,
[(1~{s},4~{s},5~{s})-4-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methanol

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
CB2 receptor agonistA cannabinoid receptor agonist that binds to and activates type 2 cannabinoid receptors.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
bone density conservation agentAn agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
apoptosis inhibitorAny substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
bridged compoundA polycyclic compound in which two rings have two or more atoms in common.
carbobicyclic compoundA bicyclic compound in which all the ring atoms are carbon.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
synthetic cannabinoidA class of cannabinoid that consists of synthetic analogs of the naturally occuring cannabinoids.
primary allylic alcoholAn allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to two hydrogens.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki10.00000.00020.566510.0000AID1127502; AID1193112
Cannabinoid receptor 2 Homo sapiens (human)Ki0.02040.00000.415610.0000AID1068376; AID1127503; AID1193111; AID1431663; AID1724600; AID1847541
[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)0.09830.00030.15173.2800AID1175690; AID1847545; AID708959; AID728643
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
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 (2)

Processvia Protein(s)Taxonomy
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 (6)

Processvia Protein(s)Taxonomy
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 (24)

Assay IDTitleYearJournalArticle
AID708959Agonist activity at human CB2 receptor expressed in CHO cells assessed as reduction in forskolin-induced cAMP accumulation incubated for 45 mins by TR-FRET method based LANCE cAMP assay2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Lead discovery, chemistry optimization, and biological evaluation studies of novel biamide derivatives as CB2 receptor inverse agonists and osteoclast inhibitors.
AID1847553Metabolic stability in rat liver microsomes assessed as intrinsic clearance2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847554Metabolic stability in mouse liver microsomes assessed as intrinsic clearance2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847549Metabolic stability in human liver microsomes assessed as half life2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847541Displacement of [3H]-CP55940 from recombinant human CB2 receptor expressed in CHO cells assessed as inhibition constant incubated for 120 mins by radioligand binding assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847550Metabolic stability in rat liver microsomes assessed as half life2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1193111Displacement of [3H]HU-243 from CB2 receptor (unknown origin) transfected in human COS7 cells2015Bioorganic & medicinal chemistry, Apr-01, Volume: 23, Issue:7
Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.
AID1431662Displacement of [3H]CP55940 from human CB1 receptor expressed in HEK293 EBNA cell membranes after 90 mins by liquid scintillation and luminescence counting method
AID1193112Binding affinity to rat CB1 receptor2015Bioorganic & medicinal chemistry, Apr-01, Volume: 23, Issue:7
Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.
AID1068376Displacement of [3H]-CP55940 from human CB2 receptor transfected in HEK-293EBNA cells after 90 mins by luminescence counting analysis2014European journal of medicinal chemistry, Feb-12, Volume: 73Cannabinoid agonists showing BuChE inhibition as potential therapeutic agents for Alzheimer's disease.
AID1431663Displacement of [3H]CP55940 from human CB2 receptor expressed in HEK293 EBNA cell membranes after 90 mins by liquid scintillation and luminescence counting method
AID728643Inverse agonist activity at human CB2 receptor expressed in CHO cells assessed as increase in forskolin-induced cAMP production after 45 mins in presence of phosphodiesterase inhibitor RO20-17242013Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5
Novel triaryl sulfonamide derivatives as selective cannabinoid receptor 2 inverse agonists and osteoclast inhibitors: discovery, optimization, and biological evaluation.
AID1847539Agonist activity at recombinant human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation by measuring maximum efficacy preincubated for 15 mins followed by forskolin stimulation and measured after 15 mins by 2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1127504Selectivity ratio of Ki for CB1 receptor of rat brain synaptosomal membranes to Ki for human CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1724600Displacement of [3H]CP55940 from human CB2R transfected in HEK293EBNA cell membrane incubated for 90 mins by Microbeta TriLux based luminescence analysis2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
New cannabinoid receptor antagonists as pharmacological tool.
AID1724608Agonist activity at CB2 receptor in mouse MC3T3-E1 cells assessed as induction of bone activity by measuring increase in collagen I gene expression at 0.01 to 1 uM incubated for 72 hrs by real time PCR analysis2020Bioorganic & medicinal chemistry, 10-01, Volume: 28, Issue:19
New cannabinoid receptor antagonists as pharmacological tool.
AID1847551Metabolic stability in mouse liver microsomes assessed as half life2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847552Metabolic stability in human liver microsomes assessed as intrinsic clearance2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1127502Displacement of [3H]HU-243 from CB1 receptor of rat brain synaptosomal membranes2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1175690Agonist activity at human CB2R expressed in CHO cells assessed as reduction in forskolin-induced cAMP accumulation by beta-galactosidase based complementation immunoassay2015Bioorganic & medicinal chemistry, Jan-01, Volume: 23, Issue:1
Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists.
AID1847547Agonist activity at recombinant human CB1 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation at 10 uM preincubated for 15 mins followed by forskolin stimulation and measured after 15 mins by HTRF assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1127503Displacement of [3H]HU-243 from human CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID1847542Displacement of [3H]-CP55940 from recombinant human CB1 receptor expressed in CHO cells at 10 uM incubated for 120 mins by radioligand binding assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
AID1847545Agonist activity at recombinant human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation preincubated for 15 mins followed by forskolin stimulation and measured after 15 mins by HTRF assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Carbon-silicon switch led to the discovery of novel synthetic cannabinoids with therapeutic effects in a mouse model of multiple sclerosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (76)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.32)18.2507
2000's13 (17.11)29.6817
2010's42 (55.26)24.3611
2020's20 (26.32)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (3.95%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other73 (96.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]