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2-Arachidonoylglycerol

Athanor · official

C23H38O4 · 378.5 g/mol

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

Also called 2-AG, endocannabinoid

HormonesLipids
Open in Athanor
The structure of 2-Arachidonoylglycerol
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Synonyms
2-AG, endocannabinoid, 2-Arachidonylglycerol
+ 35 more

2-Arachidonyl-glycerol, 2-Arachidonoyl-glycerol, glyceryl 2-arachidonate, 2-Ara-Gl, 2-Monoarachidonoylglycerol, 8D239QDW64, 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, (5Z,8Z,11Z,14Z)-, CHEBI:52392, DTXSID001017454, 1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate, RefChem:85501, DTXCID30890234, 2-Arachidonoyl Glycerol, 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate, 2-Arachidonyl glycerol, UNII-8D239QDW64, CHEMBL122972, 2-AG-D8, 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol, 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol, MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0), 2-Arachidonoyl-sn-glycerol, 2-arachidonoylglycero, BSPBio_001413, GTPL729, SCHEMBL136277, BML3-F09, orb1707757, 2-arachidonoylglycerol (2-AG), 5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glyceryl ester, BDBM26144, FA028, HMS1361G15, HMS1791G15

Molecular formula
C23H38O4
Empirical formula
C23H38O4
Molecular weight
378.5 g/mol
Exact mass
378.27701
CAS number
53847-30-6
PubChem CID
5282280
Canonical SMILES
CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO
Isomeric 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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
27
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.61
H-bond donors
2
H-bond acceptors
4
Rotatable bonds
17 computed here · PubChem 18
TPSA (Ų)
66.8
Formal charge
0
XLogP3
5.3 PubChem
Complexity
445 PubChem
Stereocenters
None
Double-bond geometry
C6=C7: Z · C9=C10: Z · C12=C13: Z · C15=C16: Z
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C72.98%
  • H10.12%
  • O16.91%

Isotope pattern

100%378.27725%379.2803.9%380.283381.286

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
5.03 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-4.23 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.02 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 378.55
  • log P ≤ 5 (Crippen): 5.03
  • H-bond donors ≤ 5: 2
  • H-bond acceptors ≤ 10: 4

Breaks 1 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: eMolecules, AbaChemScene, ChemoSapiens.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  5. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  6. ·Literature on PubChem

Data last updated 2026-10-14.