1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

• ChemBase ID: 160789
• Molecular Formular: C23H38O4
• Molecular Mass: 378.54542
• Monoisotopic Mass: 378.2770097
• SMILES: C(OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)(CO)CO
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
• InChI: InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-
• InChIKey: RCRCTBLIHCHWDZ-DOFZRALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• IUPAC Traditional name: 2-arachidonylglycerol
• Synonyms: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid 2-Hydroxy-1-(hydroxymethyl)ethyl Ester; (all-Z)-5,8,11,14-Eicosatetraenoic Acid 2-Hydroxy-1-(hydroxymethyl)ethyl Ester; 2-Monoarachidonoylglycerol; 2-Arachidonyl Glycerol

Database IDs

• CAS Number: 53847-30-6
• PubChem SID: 162254924
• PubChem CID: 5282280

CALCULATED PROPERTIES

• Acid pKa: 14.278373
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.4126277
• LogD (pH = 7.4): 5.4126277
• Log P: 5.4126277
• Molar Refractivity: 116.9779 cm^3
• Polarizability: 44.134323 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A765050

2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats.

REFERENCES

• Yokotani, K., et al.: Eur. J. Pharmacol., 512, 29 (2005)
• Jensen, R., et al.: Pharmacol. Rev., 60, 1 (2005)
• Lu, L., et al.: Eur. J. Pharmacol., 590, 177 (2005)