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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42O3
Molecular Weight 414.6216
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HU-308

SMILES

CCCCCCC(C)(C)c1cc(c([C@]2([H])C=C(CO)[C@]3([H])C[C@@]2([H])C3(C)C)c(c1)OC)OC

InChI

InChIKey=CFMRIVODIXTERW-BHIFYINESA-N
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-/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H42O3
Molecular Weight 414.6216
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20218623 | https://www.ncbi.nlm.nih.gov/pubmed/16407142 | https://www.ncbi.nlm.nih.gov/pubmed/27634891

HU-308 ([(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol) is a potent, selective agonist for the CB2 receptor. The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s. It has analgesic effects, promotes proliferation of neural stem cells,[3] and protects both liver and blood vessel tissues against oxidative stress via inhibition of TNF-α. In vivo, HU-308 has hypotensive, analgesic, and anti-inflammatory activities in mice that can be reversed by the CB2 receptor antagonist SR 144528 but not the CB1 receptor antagonist rimonabant. Pretreatment of mice with HU-308 decreases the I/R-induced tissue damage, inflammatory cell infiltration, tissue, and serum TNF-α, MIP-1, and MIP-2 levels, tissue lipid peroxidation, and apoptosis. HU-308 increases proliferation of HT29 colon cancer cells and growth of tumors in an HT29 mouse xenograft model. The physiological and toxicological properties of this compound have not been evaluated in humans.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor.
1999 Dec 7
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
2008 Oct 15
Patents

Patents

Sample Use Guides

Rats were treated with HU-308 (0.3-30 mg/kg i.p.)
Route of Administration: Intraperitoneal
Cells were set up 4x103 cells per well of a 96-well plate and were cultured in DMEM medium supplemented with 10% FCS overnight. The medium was replaced for serum-free DMEM medium and cells were incubated for 48h with HU-308 (0.001, 0.01, 0.1, 1 and 10mkM). Cell viability was assayed by Cell Counting Kit-8 (CCK-8).
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:05:26 UTC 2021
Edited
by admin
on Sat Jun 26 15:05:26 UTC 2021
Record UNII
8I5L034D55
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HU-308
Common Name English
(+)-HU-308
Common Name English
BICYCLO(3.1.1)HEPT-2-ENE-2-METHANOL, 4-(4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL)-6,6-DIMETHYL-, (1R,4R,5R)-
Systematic Name English
BICYCLO(3.1.1)HEPT-2-ENE-2-METHANOL, 4-(4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL)-6,6-DIMETHYL-, (1R,4R,5R)-REL-(+)-
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 734920
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
Code System Code Type Description
PUBCHEM
5311172
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
PRIMARY
CAS
256934-39-1
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
CAS
1220887-84-2
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
PRIMARY
FDA UNII
8I5L034D55
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
PRIMARY
WIKIPEDIA
HU-308
Created by admin on Sat Jun 26 15:05:26 UTC 2021 , Edited by admin on Sat Jun 26 15:05:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY