Anandamide

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	dd50e867-5afd-4f45-a7bf-ad7c858e30e3
Taxonomy	Organic nitrogen compounds > Organonitrogen compounds > Amines > Alkanolamines > 1,2-aminoalcohols > N-acylethanolamines
IUPAC Name	(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
SMILES (Canonical)	CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO
SMILES (Isomeric)	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChI	InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChI Key	LGEQQWMQCRIYKG-DOFZRALJSA-N
Popularity	5,606 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₂H₃₇NO₂
Molecular Weight	347.50 g/mol
Exact Mass	347.282429423 g/mol
Topological Polar Surface Area (TPSA)	49.30 Å²
XlogP	5.40
Atomic LogP (AlogP)	5.24
H-Bond Acceptor	2
H-Bond Donor	2
Rotatable Bonds	16

Synonyms

Top

Arachidonylethanolamide

94421-68-8

Arachidonoyl ethanolamide

N-Arachidonoylethanolamine

N-arachidonoyl ethanolamine

arachidonoylethanolamide

(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide

AEA

Anandamide (20.4, n-6)

N-Arachidonoyl-2-hydroxyethylamide

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9777	97.77%
Caco-2	-	0.7115	71.15%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4551	45.51%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	-	0.4497	44.97%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7402	74.02%
P-glycoprotein inhibitior	-	0.5772	57.72%
P-glycoprotein substrate	-	0.6948	69.48%
CYP3A4 substrate	-	0.5709	57.09%
CYP2C9 substrate	-	0.6108	61.08%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.8383	83.83%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8531	85.31%
CYP inhibitory promiscuity	-	0.9112	91.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.5881	58.81%
Eye corrosion	-	0.8106	81.06%
Eye irritation	-	0.8567	85.67%
Skin irritation	-	0.6866	68.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6595	65.95%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6089	60.89%
skin sensitisation	-	0.9386	93.86%
Respiratory toxicity	-	0.7667	76.67%
Reproductive toxicity	-	0.5764	57.64%
Mitochondrial toxicity	-	0.8750	87.50%
Nephrotoxicity	+	0.4907	49.07%
Acute Oral Toxicity (c)	III	0.5354	53.54%
Estrogen receptor binding	+	0.6949	69.49%
Androgen receptor binding	-	0.8472	84.72%
Thyroid receptor binding	+	0.6635	66.35%
Glucocorticoid receptor binding	+	0.5433	54.33%
Aromatase binding	-	0.5175	51.75%
PPAR gamma	+	0.8653	86.53%
Honey bee toxicity	-	0.9877	98.77%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5080	50.80%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	10000 nM	Potency	via CMAUP
CHEMBL2243	O00519	Anandamide amidohydrolase	3400 nM	IC50	PMID: 18983142
CHEMBL1293237	P54132	Bloom syndrome protein	35481.3 nM	Potency	via CMAUP
CHEMBL218	P21554	Cannabinoid CB1 receptor	72 nM 11 nM 72 nM 89 nM 70 nM 72 nM 70 nM 70 nM 50 nM 70 nM 72 nM 72 nM	Ki Ki Ki Ki Ki Ki Ki Ki Ki Ki Ki Ki	PMID: 16213718 via Super-PRED PMID: 25065940 PMID: 23865723 PMID: 22044209 PMID: 19331413 PMID: 19161308 PMID: 16682198 PMID: 16078824 PMID: 16570929 PMID: 16279794 PMID: 17561406
CHEMBL253	P34972	Cannabinoid CB2 receptor	180 nM 180 nM 180 nM 180 nM 160 nM	Ki Ki Ki Ki Ki	PMID: 19161308 PMID: 16682198 PMID: 16570929 PMID: 16213718 via Super-PRED
CHEMBL4794	Q8NER1	Vanilloid receptor	15.8 nM 490 nM 630 nM 200 nM 15.8 nM	EC50 EC50 EC50 EC50 EC50	PMID: 23384387 PMID: 16570929 PMID: 23865723 PMID: 19361197 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	97.99%	99.17%
CHEMBL2581	P07339	Cathepsin D	97.46%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	97.26%	89.63%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.31%	97.29%
CHEMBL2664	P23526	Adenosylhomocysteinase	91.42%	86.67%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.55%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.25%	96.09%
CHEMBL1781	P11387	DNA topoisomerase I	87.25%	97.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.76%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.33%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.04%	94.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.67%	89.34%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.54%	96.95%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	83.54%	96.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.92%	91.11%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.60%	100.00%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	80.99%	89.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.62%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.06%	94.73%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Alstroemeria revoluta

Astragalus tragacantha

Baphia nitida

Chamaecyparis lawsoniana

Corynanthe mayumbensis

Crataegus viridis var. ovata

Crinum erubescens

Cylindrolobus foetidus