CHEBI:146244 - HU-308

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ChEBI Name HU-308
ChEBI ID CHEBI:146244
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
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Formula C27H42O3
Net Charge 0
Average Mass 414.630
Monoisotopic Mass 414.31340
InChI InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21+,22-/m0/s1
InChIKey CFMRIVODIXTERW-BDTNDASRSA-N
SMILES [C@@H]1(C=C([C@@H]2C([C@H]1C2)(C)C)CO)C=3C(=CC(=CC3OC)C(CCCCCC)(C)C)OC
Roles Classification
Biological Role(s): CB2 receptor agonist
A cannabinoid receptor agonist that binds to and activates type 2 cannabinoid receptors.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
bone density conservation agent
An 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.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing HU-308 (CHEBI:146244) has role anti-inflammatory agent (CHEBI:67079)
HU-308 (CHEBI:146244) has role antihypertensive agent (CHEBI:35674)
HU-308 (CHEBI:146244) has role apoptosis inhibitor (CHEBI:68494)
HU-308 (CHEBI:146244) has role bone density conservation agent (CHEBI:50646)
HU-308 (CHEBI:146244) has role CB2 receptor agonist (CHEBI:146246)
HU-308 (CHEBI:146244) is a aromatic ether (CHEBI:35618)
HU-308 (CHEBI:146244) is a bridged compound (CHEBI:35990)
HU-308 (CHEBI:146244) is a carbobicyclic compound (CHEBI:36785)
HU-308 (CHEBI:146244) is a primary allylic alcohol (CHEBI:134394)
HU-308 (CHEBI:146244) is a synthetic cannabinoid (CHEBI:67201)
IUPAC Name
{(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
Synonyms Sources
(+)-{(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
HU 308 ChEBI
HU308 ChEBI
Manual Xref Database
HU-308 Wikipedia
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Citations Waiting for Citations Types Sources
10588688 PubMed citation Europe PMC
17652447 PubMed citation Europe PMC
21542549 PubMed citation Europe PMC
26124120 PubMed citation Europe PMC
26846967 PubMed citation Europe PMC
29450258 PubMed citation Europe PMC
30372893 PubMed citation Europe PMC
Last Modified
12 March 2020
General Comment
2020-03-12 One of the "HU cannabinoids" synthesised by Raphael Mechoulam's research group at Hebrew University.