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

Details

• Internal ID: 2649866c-92d2-4c09-abb0-e158ee8b75b7
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphocholines > Lysophosphatidylcholines > 1-acyl-sn-glycero-3-phosphocholines
• IUPAC Name: [(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• InChI: InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
• InChI Key: YAMUFBLWGFFICM-PTGWMXDISA-N
• Popularity: 103 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₅₂NO₇P
• Molecular Weight: 521.70 g/mol
• Exact Mass: 521.34814000 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.14
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 24

Synonyms

• [(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• ((2R)-2-hydroxy-3-((Z)-octadec-9-enoyl)oxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
• RefChem:1054577
• 19420-56-5
• 1-Oleoyl-sn-glycero-3-phosphocholine
• LPC 18:1
• oleoyl-lysophosphatidylcholine
• 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine
• 1-O-Oleoyl-sn-glycero-3-phosphocholine
• 18:1 Lyso PC
• L-Alpha-Lysophosphatidylcholine,oleoyl
• PC(18:1(9Z)/0:0)
• 1-Oleoyl-sn-glycero-3-phosphorylcholine
• lysophosphatidylcholine 18:1
• CHEBI:28610
• L-alpha-LYSOPHOSPHATIDYLCHOLINE, OLEOYL
• Choline, phosphate 3-ester with 1-monoolein, L-
• PC(18:1/0:0)
• 1-Oleoylglycerophosphocholine
• (R,Z)-2-Hydroxy-3-(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
• Choline, hydroxide, dihydrogen phosphate, inner salt, 3-ester with 1-monoolein, L-
• Olein, 1-mono-, 3-(dihydrogen phosphate), monoester with choline hydroxide, inner salt, L-
• LPC(18:1/0:0)
• C26H52NO7P
• MFCD00133435
• (R,Z)-2-Hydroxy-3-(oleoyloxy)propyl [2-(Trimethylammonio)ethyl] Phosphate
• Oleoyl lysolecithin
• 1-18:1-lysoPC
• Epitope ID:241571
• 1-Oleoyllysophosphatidylcholine
• Lyso-PC 18:1(9Z)
• Lysophosphatidylcholine C18:1
• FS74G26ZZ4
• GTPL3623
• orb1298691
• CHEMBL3093102
• LysoPIC(18:1/0:0)
• SCHEMBL19821339
• YAMUFBLWGFFICM-PTGWMXDISA-N
• DTXSID201334331
• 1-18:1-2-lysophosphatidylcholine
• MSK40279
• LMGP01050032
• LysoPC(18:1(9Z)/0:0)
• AKOS024407403
• EBC-616993
• HY-W140439
• (2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• GPCho(18:1(9Z)/0:0)[rac]
• BP-29613
• FO158106
• SY328456
• 1-Oleoyl-sn-glycerol-3-phosphatidylcholine
• Choline phosphate 3-ester with 1-monoolein
• DB-222738
• CS-0199016
• NS00074214
• Olein-1-mono-3-phosphate ester with choline
• D81955
• Choline phosphate (ester) 3-ester with 1-monoolein
• Q27088173
• (R)-2-Hydroxy-3-(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
• 18:1 Lyso PC, 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine, powder
• (2R)-2-Hydroxy-3-[(9Z)-9-Octadecenoyloxy]Propyl 2-(Trimethylammonio)Ethyl Phosphate
• (2R)-2-Hydroxy-3-{[(9Z)-octadec-9-enoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphate
• [(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxy-propyl] 2-(trimethylammonio)ethyl phosphate
• [(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropyl] 2-trimethylazaniumylethyl phosphate
• 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine, 1-cis-9-Octadecenoyl-sn-glycero-3-phosphocholine, 1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine
• 1-Oleoyl-sn-glycero-3-phosphocholine; 3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,18Z)-; 3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, [R-(Z)]-; Choline, hydroxide
• 3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,18Z)-
• 3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, [R-(Z)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9019	90.19%
Caco-2	-	0.7735	77.35%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Plasma membrane	0.6650	66.50%
OATP2B1 inhibitior	-	0.5735	57.35%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7077	70.77%
P-glycoprotein inhibitior	+	0.5730	57.30%
P-glycoprotein substrate	-	0.6372	63.72%
CYP3A4 substrate	+	0.6018	60.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8394	83.94%
CYP3A4 inhibition	-	0.7506	75.06%
CYP2C9 inhibition	-	0.8723	87.23%
CYP2C19 inhibition	-	0.7947	79.47%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	-	0.8726	87.26%
CYP2C8 inhibition	-	0.6003	60.03%
CYP inhibitory promiscuity	-	0.9825	98.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.5742	57.42%
Eye corrosion	-	0.9211	92.11%
Eye irritation	-	0.8200	82.00%
Skin irritation	-	0.7669	76.69%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4162	41.62%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8011	80.11%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7326	73.26%
Acute Oral Toxicity (c)	III	0.5132	51.32%
Estrogen receptor binding	+	0.7602	76.02%
Androgen receptor binding	-	0.6911	69.11%
Thyroid receptor binding	-	0.5699	56.99%
Glucocorticoid receptor binding	-	0.5746	57.46%
Aromatase binding	-	0.5233	52.33%
PPAR gamma	-	0.5069	50.69%
Honey bee toxicity	-	0.8560	85.60%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.7124	71.24%
Fish aquatic toxicity	+	0.7366	73.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.81%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	98.47%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	95.68%	89.63%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.57%	92.86%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.13%	92.08%
CHEMBL321	P14780	Matrix metalloproteinase 9	92.98%	92.12%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	91.83%	85.94%
CHEMBL4588	P22894	Matrix metalloproteinase 8	89.49%	94.66%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.68%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	86.83%	91.81%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.08%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.81%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.51%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.32%	100.00%
CHEMBL1781	P11387	DNA topoisomerase I	83.68%	97.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.77%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.66%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	82.47%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.42%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	82.23%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.08%	93.03%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.89%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.67%	96.90%
CHEMBL202	P00374	Dihydrofolate reductase	80.50%	89.92%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 16081932
• LOTUS: LTS0090139
• wikiData: Q27088173