n-Oleoylethanolamine

Details

• Internal ID: bd853257-d930-43f1-b379-5334a55f3659
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Alkanolamines > 1,2-aminoalcohols > N-acylethanolamines
• IUPAC Name: (Z)-N-(2-hydroxyethyl)octadec-9-enamide
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)NCCO
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)NCCO
• InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
• InChI Key: BOWVQLFMWHZBEF-KTKRTIGZSA-N
• Popularity: 344 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₉NO₂
• Molecular Weight: 325.50 g/mol
• Exact Mass: 325.298079487 g/mol
• Topological Polar Surface Area (TPSA): 49.30 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.13
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 17

Synonyms

• oleoylethanolamide
• 111-58-0
• N-(2-Hydroxyethyl)oleamide
• Oleylethanolamide
• Oleamide MEA
• N-oleoyl ethanolamine
• Oleoyl Ethanolamide
• Oleoyl monoethanolamide
• (Z)-N-(2-hydroxyethyl)octadec-9-enamide
• N-oleoylethanolamide
• OLEIC MONOETHANOLAMIDE
• N-oleoyl ethanolamide
• N-(2-Hydroxyethyl)-9-octadecenamide
• N-(Hydroxyethyl)oleamide
• OEA
• Oleic acid ethanolamide
• N-(9Z-octadecenoyl)-ethanolamine
• (9Z)-N-(2-hydroxyethyl)octadec-9-enamide
• N-(cis-9-octadecenoyl) ethanolamine
• N-(hydroxyethyl) oleamide
• Oleic acid monoethanolamide
• 9-Octadecenamide, N-(2-hydroxyethyl)-
• 1HI5J9N8E6
• CHEMBL280065
• CHEBI:71466
• 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
• SR-01000076041
• EINECS 203-884-8
• UNII-1HI5J9N8E6
• N-(2-hydroxyethyl)octadec-9-enamide
• Monoethanolamine oleic acid amide
• 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-
• Olemsartan Medoximil
• MFCD00045972
• oleoyl 1-ethanolamide
• Tocris-1484
• N-Oleoyl-2-aminoethanol
• Oleoylethanolamide (OEA)
• Spectrum5_002037
• Lopac-O-0383
• OLEAMIDE MEA [INCI]
• Lopac0_000942
• MLS002153155
• SCHEMBL177713
• GTPL2661
• DTXSID1044516
• BDBM29080
• N-(9Z-octadecenoyl) ethanolamine
• HMS2233E21
• HMS3262N06
• HMS3412D21
• HMS3649J05
• HMS3676D21
• OLEYLETHANOLAMIDE [WHO-DD]
• NAE 18:1
• Tox21_500942
• LMFA08040015
• N-Oleoylethanolamine, ~98% (TLC)
• NAE(18:1)
• AKOS015839895
• N-(2-Hydroxyethyl)-9Z-octadecenamide
• CCG-205023
• LP00942
• SDCCGSBI-0050916.P002
• NCGC00015761-01
• NCGC00015761-02
• NCGC00015761-03
• NCGC00015761-04
• NCGC00015761-05
• NCGC00015761-06
• NCGC00015761-07
• NCGC00015761-12
• NCGC00025182-01
• NCGC00025182-02
• NCGC00025182-04
• NCGC00025182-05
• NCGC00025182-06
• NCGC00261627-01
• AS-15152
• SMR001230650
• (9Z)-N-(2-Hydroxyethyl)-9-octadecenamide
• HY-107542
• CS-0028847
• EU-0100942
• O0345
• Oleic acid monoethanolamideN-Oleoylethanolamide
• C20792
• D82195
• O 0383
• 9-OCTADECENAMIDE, N-(2-HYDROXYETHYL)-, Z
• A802386
• Q7086404
• SR-01000076041-1
• SR-01000076041-3
• SR-01000076041-8
• W-109412
• C18:1 anandamide, 9Z-octadecenoylethanolamide, powder
• (Z)-N-(2-hydroxyethyl)octadec-9-enamide;Oleoylethanolamide
• N-Oleoylethanolamide; Oleamide MEA; Oleic acid monoethanolamide
• N-oleoyl ethanolamine, Oleoyl monoethanolamide, Oleoylethanolamide
• 5YM

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9777	97.77%
Caco-2	+	0.4899	48.99%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4551	45.51%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.8023	80.23%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7285	72.85%
P-glycoprotein inhibitior	-	0.7725	77.25%
P-glycoprotein substrate	-	0.7137	71.37%
CYP3A4 substrate	-	0.5851	58.51%
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	-	0.8967	89.67%
CYP inhibitory promiscuity	-	0.9112	91.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.5881	58.81%
Eye corrosion	-	0.8106	81.06%
Eye irritation	+	0.6986	69.86%
Skin irritation	-	0.6866	68.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4079	40.79%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6480	64.80%
skin sensitisation	-	0.9386	93.86%
Respiratory toxicity	-	0.9667	96.67%
Reproductive toxicity	-	0.5764	57.64%
Mitochondrial toxicity	-	0.8750	87.50%
Nephrotoxicity	+	0.5602	56.02%
Acute Oral Toxicity (c)	III	0.5354	53.54%
Estrogen receptor binding	-	0.4894	48.94%
Androgen receptor binding	-	0.8008	80.08%
Thyroid receptor binding	+	0.6942	69.42%
Glucocorticoid receptor binding	-	0.7231	72.31%
Aromatase binding	-	0.7333	73.33%
PPAR gamma	+	0.7082	70.82%
Honey bee toxicity	-	0.9868	98.68%
Biodegradation	+	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7850	78.50%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	112.2 nM	Potency	via Super-PRED
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	110 nM	EC50	via Super-PRED
CHEMBL4794	Q8NER1	Vanilloid receptor	40 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.67%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	98.01%	89.63%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	96.52%	97.29%
CHEMBL2581	P07339	Cathepsin D	96.49%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.64%	92.08%
CHEMBL2664	P23526	Adenosylhomocysteinase	92.37%	86.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.82%	91.11%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	87.64%	96.67%
CHEMBL1781	P11387	DNA topoisomerase I	87.16%	97.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.96%	89.34%
CHEMBL2885	P07451	Carbonic anhydrase III	86.92%	87.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.83%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	85.79%	98.03%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	84.35%	89.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.94%	92.86%
CHEMBL4179	P45984	c-Jun N-terminal kinase 2	83.60%	90.75%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.60%	91.81%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.44%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.00%	91.24%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.68%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.95%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	81.92%	92.50%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.04%	93.10%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5283454
• LOTUS: LTS0000206
• wikiData: Q7086404