2-Arachidonoylglycerol

Details

• Internal ID: 9ce73ae0-fb04-4aae-8c5c-d8f8db8ec56a
• Taxonomy: Lipids and lipid-like molecules > Endocannabinoids
• IUPAC Name: 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• SMILES (Canonical): CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO
• SMILES (Isomeric): 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-
• InChI Key: RCRCTBLIHCHWDZ-DOFZRALJSA-N
• Popularity: 2,783 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₈O₄
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.27700969 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.03
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 17

Synonyms

• 53847-30-6
• 2-Arachidonylglycerol
• 2-AG
• 2-Arachidonoyl-glycerol
• 2-Arachidonoyl Glycerol
• 2-Arachidonyl glycerol
• 2-Arachidonyl-glycerol
• glyceryl 2-arachidonate
• 2-Ara-Gl
• 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CHEMBL122972
• 924894-97-3
• CHEBI:52392
• 2-AG-D8
• 8D239QDW64
• 5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,8Z,11Z,14Z)-
• 5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (all-Z)-
• MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol
• 2-Monoarachidonoylglycerol
• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol
• UNII-8D239QDW64
• 2-arachidonoylglycero
• 2-Oarachidonoyl Glycerol
• 2-Arachidonoyl-sn-glycerol
• BSPBio_001413
• GTPL729
• SCHEMBL136277
• BML3-F09
• 2-arachidonoylglycerol (2-AG)
• 5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glyceryl ester
• BDBM26144
• DTXSID001017454
• FA028
• HMS1361G15
• HMS1791G15
• HMS1989G15
• HMS3402G15
• HMS3649C03
• LMGL01010023
• PDSP1_000803
• PDSP2_000790
• AKOS024456515
• MAG(0:0/20:4n6)
• MAG(0:0/20:4w6)
• CS-W011767
• HY-W011051
• IDI1_033883
• MG(0:0/20:4n6)
• MG(0:0/20:4w6)
• NCGC00161389-01
• NCGC00161389-02
• NCGC00161389-03
• NCGC00161389-04
• 2-Monoarachidonoylglycerolbeta-monoacylglycerol
• F85611
• L000057
• Q209320
• SR-01000946555
• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycerol
• SR-01000946555-1
• W-204228
• 2-Arachidonyl glycerol, ~10 mg/mL, >=98% (HPLC)
• BRD-K71198913-001-02-3
• 5Z,8Z,11Z,14Z-eicosatetraenoicacid,2-glycerol-1,1,2,3,3-d5ester
• 1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate
• (5Z,8Z,11Z,14Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoate
• (5Z,8Z,11Z,14Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoic acid
• (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
• (5Z,8Z,11Z,14Z)-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
• (all-Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoate
• (all-Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoic acid
• [2-hydroxy-1-(hydroxymethyl)ethyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8808	88.08%
Caco-2	-	0.8126	81.26%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6969	69.69%
OATP2B1 inhibitior	-	0.7140	71.40%
OATP1B1 inhibitior	-	0.4239	42.39%
OATP1B3 inhibitior	+	0.9282	92.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7838	78.38%
BSEP inhibitior	+	0.7522	75.22%
P-glycoprotein inhibitior	+	0.5906	59.06%
P-glycoprotein substrate	-	0.9045	90.45%
CYP3A4 substrate	-	0.5447	54.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8510	85.10%
CYP2C9 inhibition	-	0.8669	86.69%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.8916	89.16%
CYP1A2 inhibition	-	0.6876	68.76%
CYP2C8 inhibition	-	0.8076	80.76%
CYP inhibitory promiscuity	-	0.8350	83.50%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8223	82.23%
Carcinogenicity (trinary)	Non-required	0.6971	69.71%
Eye corrosion	-	0.9722	97.22%
Eye irritation	-	0.7425	74.25%
Skin irritation	-	0.8075	80.75%
Skin corrosion	-	0.9728	97.28%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6951	69.51%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8976	89.76%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.9732	97.32%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.4847	48.47%
Acute Oral Toxicity (c)	IV	0.5487	54.87%
Estrogen receptor binding	+	0.6835	68.35%
Androgen receptor binding	-	0.7939	79.39%
Thyroid receptor binding	+	0.5236	52.36%
Glucocorticoid receptor binding	+	0.6443	64.43%
Aromatase binding	-	0.5899	58.99%
PPAR gamma	+	0.7274	72.74%
Honey bee toxicity	-	0.9639	96.39%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6402	64.02%
Fish aquatic toxicity	+	0.8769	87.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL218	P21554	Cannabinoid CB1 receptor	23 nM	EC50	via Super-PRED
CHEMBL253	P34972	Cannabinoid CB2 receptor	17 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	97.97%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	96.36%	89.63%
CHEMBL2581	P07339	Cathepsin D	96.28%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.75%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.72%	97.29%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.50%	85.94%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.10%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.73%	93.56%
CHEMBL1781	P11387	DNA topoisomerase I	86.44%	97.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.20%	92.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.13%	92.86%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.42%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.51%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.07%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.45%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.41%	86.33%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.28%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5282280
• LOTUS: LTS0231077
• wikiData: Q209320