1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine

Details

• Internal ID: 3f51b246-79bb-4df2-b293-261ff3c05abd
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphoethanolamines > Lysophosphatidylethanolamines > 1-acyl-sn-glycero-3-phosphoethanolamines
• IUPAC Name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] (Z)-octadec-9-enoate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)OCCN)O
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN)O
• InChI: InChI=1S/C23H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h9-10,22,25H,2-8,11-21,24H2,1H3,(H,27,28)/b10-9-/t22-/m1/s1
• InChI Key: PYVRVRFVLRNJLY-MZMPXXGTSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₄₆NO₇P
• Molecular Weight: 479.60 g/mol
• Exact Mass: 479.30118980 g/mol
• Topological Polar Surface Area (TPSA): 128.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 5.02
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 23

Synonyms

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine
• O-LysoPE
• PE(18:1(9Z)/0:0)
• 1-Oleoyl-sn-glycero-3-phosphoethanolamine
• LPE(18:1/0:0)
• LysoPE(18:1/0:0)
• Lyso-PE(18:1/0:0)
• PE(18:1/0:0)
• LysoPE(18:1(9Z)/0:0)
• Lysophosphatidylethanolamine(18:1/0:0)
• [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] (Z)-octadec-9-enoate
• 1-Oleoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamine
• CHEBI:74971
• 9-Octadecenoic acid (Z)-, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-
• 1-18:1-lysophosphatidylethanolamine
• 9-Octadecenoic acid (9Z)-, (2R)-3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester
• SCHEMBL274999
• CHEMBL3262734
• LPE(18:1omega9/0:0)
• LysoPE(18:1omega9/0:0)
• CHEBI:75168
• EX-A8005F
• LysoPE(18:1n9/0:0)
• LysoPE(18:1w9/0:0)
• Lyso-PE(18:1omega9/0:0)
• Lyso-PE(18:1n9/0:0)
• Lyso-PE(18:1w9/0:0)
• LMGP02050004
• AKOS037647728
• LPE(18:1n9/0:0)
• LPE(18:1w9/0:0)
• 9-Octadecenoic acid (9Z)-,3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-
• AS-74594
• Lysophosphatidylethanolamine(18:1n9/0:0)
• Lysophosphatidylethanolamine(18:1w9/0:0)
• Lysophosphatidylethanolamine(18:1omega9/0:0)
• 1-C18:1(omega-9)-lysophosphatidylethanolamine
• 1-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine
• Q27145156
• (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-2-hydroxypropyl oleate
• (2R)-3-[(2-azaniumylethyl phosphonato)oxy]-2-hydroxypropyl (9Z)-octadec-9-enoate
• (2R)-3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-hydroxypropyl (9Z)-octadec-9-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4715	47.15%
Caco-2	-	0.8140	81.40%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5726	57.26%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8614	86.14%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7219	72.19%
P-glycoprotein inhibitior	-	0.5125	51.25%
P-glycoprotein substrate	-	0.7036	70.36%
CYP3A4 substrate	+	0.5639	56.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8095	80.95%
CYP3A4 inhibition	-	0.7008	70.08%
CYP2C9 inhibition	-	0.8542	85.42%
CYP2C19 inhibition	-	0.7525	75.25%
CYP2D6 inhibition	-	0.8562	85.62%
CYP1A2 inhibition	-	0.7426	74.26%
CYP2C8 inhibition	-	0.6789	67.89%
CYP inhibitory promiscuity	-	0.9345	93.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6838	68.38%
Carcinogenicity (trinary)	Non-required	0.5680	56.80%
Eye corrosion	-	0.8329	83.29%
Eye irritation	-	0.8534	85.34%
Skin irritation	-	0.7596	75.96%
Skin corrosion	-	0.8061	80.61%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4258	42.58%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8332	83.32%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7384	73.84%
Acute Oral Toxicity (c)	III	0.5876	58.76%
Estrogen receptor binding	+	0.7236	72.36%
Androgen receptor binding	-	0.6809	68.09%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6521	65.21%
Aromatase binding	-	0.5929	59.29%
PPAR gamma	+	0.5831	58.31%
Honey bee toxicity	-	0.8658	86.58%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6724	67.24%
Fish aquatic toxicity	+	0.8031	80.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	99.24%	97.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.82%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.74%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	96.82%	85.94%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.18%	92.86%
CHEMBL2885	P07451	Carbonic anhydrase III	93.92%	87.45%
CHEMBL2581	P07339	Cathepsin D	93.21%	98.95%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.18%	100.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	92.98%	94.01%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.67%	96.95%
CHEMBL221	P23219	Cyclooxygenase-1	92.44%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.92%	94.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.66%	89.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.42%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.06%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.77%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.36%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.16%	91.71%
CHEMBL230	P35354	Cyclooxygenase-2	83.80%	89.63%
CHEMBL3401	O75469	Pregnane X receptor	83.53%	94.73%
CHEMBL1907	P15144	Aminopeptidase N	82.99%	93.31%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	82.71%	92.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.67%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.62%	87.67%
CHEMBL340	P08684	Cytochrome P450 3A4	82.13%	91.19%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.04%	96.00%
CHEMBL4333	P21453	Sphingosine 1-phosphate receptor Edg-1	81.93%	96.99%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.39%	80.33%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.21%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.06%	97.21%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.86%	93.03%
CHEMBL1781	P11387	DNA topoisomerase I	80.55%	97.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.55%	95.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.12%	93.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9547071
• LOTUS: LTS0250903
• wikiData: Q27145156