1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

Details

• Internal ID: 1dee52df-d866-4ae2-a99b-8abe1f3be1a4
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphocholines > Phosphatidylcholines
• IUPAC Name: [(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
• InChI: InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1
• InChI Key: WTJKGGKOPKCXLL-VYOBOKEXSA-N
• Popularity: 2,116 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₈₂NO₈P
• Molecular Weight: 760.10 g/mol
• Exact Mass: 759.57780557 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 13.60
• Atomic LogP (AlogP): 11.17
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 39

Synonyms

• 26853-31-6
• 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
• Palmitoyloleoylphosphatidylcholine
• 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC
• PC(16:0/18:1(9Z))
• 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
• [(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• MFCD00077387
• 70778-75-5
• 1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine
• GPCho(34:1)
• (R,Z)-2-(Oleoyloxy)-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
• PC(16:0/18:1w9)
• Phosphatidylcholine(16:0/18:1)
• 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine
• C42H82NO8P
• TE895536Y5
• (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• 1-16:0-2-18:1-phosphatidylcholine
• L-beta-Oleoyl-gamma-palmitoyl-alpha-lecithin
• (R)-2-(oleoyloxy)-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
• 16:0-18:1-PC
• (R)-(Z)-(4-Oxido-9-oxo-7-(palmitoylmethyl)-3,5,8-trioxa-4-phosphahexacos-17-enyl)trimethylammonium 4-oxide
• L-b-Oleoyl-g-palmitoyl-a-lecithin
• PC 34:1
• (R,Z)-2-(Oleoyloxy)-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphate
• [3-hexadecanoyloxy-2-[(E)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• (2R)-3-(hexadecanoyloxy)-2-{[(9Z)-octadec-9-enoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphate
• UNII-TE895536Y5
• Ptd-Cho
• 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (main component of Egg Phosphatidylcholines / EPC, CAS 97281-44-2)
• EINECS 248-056-7
• 1-palmitoyl-2-oleoyl-GPC
• SCHEMBL45162
• beta-Oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholine
• orb1307139
• CHEBI:73001
• GPCho(16:0/18:1omega9)
• PC(16:0/18:1omega9)
• DTXSID101029642
• CMC_12041
• CMC_12042
• EX-A11791
• LMGP01010005
• AKOS027379127
• 1-Palmitoyl-2-oleoyl-L-alpha-lecithin
• 2-Oleoyl-1-palmitoylphosphatidylcholine
• EBC-617003
• L-a-phosphatidylcholine (Egg, Chicken)
• Phosphatidylcholine(16:0/18:1omega9)
• 1-Palmitoyl-2-oleoyl-sn-3-phosphocholine
• AS-67722
• BP-26319
• BP-26332
• DA-69576
• SY074596
• phosphatidylcholine (1-16:0-2-18:1)
• GPC(16:0/18:1)
• HY-130462
• CS-0108058
• 1-Palmitoyl-2-oleoyl-3-sn-phosphatidylcholine
• 1-palmitoyl-2-oleoyl-GPC (16:0/18:1)
• 1-Palmitoyl-2-oleyl-3-sn-phosphatidylcholine
• 1-Palmitoyl-2-oleoyl-sn-glycero-phosphocholine
• 16:0-18:1 PC
• 3-sn-Phosphatidylcholine, 2-oleoyl-1-palmitoyl
• L-alpha-1-Palmitoyl-2-oleoylphosphatidylcholine
• 1-Palmitoyl-2-oleoyl-L-alpha-phosphatidylcholine
• A905125
• 1-hexadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine
• 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylcholine
• 1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylcholine
• 1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylcholine
• Q10860475
• 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (popc)
• 1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphatidylcholine
• Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC)
• Egg PC, L-alpha-phosphatidylcholine (Egg, Chicken), powder
• Brain PC, L-alpha-phosphatidylcholine (Brain, Porcine), powder
• 1-Hexadecanoyl-2-(cis-9-octadecenoyl)-sn-glycero-3-phosphocholine
• Brain PC, L-alpha-phosphatidylcholine (Brain, Porcine), chloroform
• 16:0-18:1 PC, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, powder
• (2R)-2-[(9Z)-9-Octadecenoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphate
• (R,Z)-2-(Oleoyloxy)-3-(palmitoyloxy)propyl(2-(trimethylammonio)ethyl)phosphate
• 16:0-18:1 PC, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, chloroform
• -N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-, hydroxide, inner salt, 4-oxide, [R-(Z)]-
• [(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxy-propyl] 2-(trimethylammonio)ethyl phosphate
• 3,5,8-TRIOXA-4-PHOSPHAHEXACOS-17-EN-1-AMINIUM, 4-HYDROXY-N,N,N-TRIMETHYL-9-OXO-7-(((1-OXOHEXADECYL)OXY)METHYL)-, INNER SALT, 4-OXIDE, (7R,17Z)-
• 3,5,8-Trioxa-4-phosphahexacos-17-en-1-aminium, 4-hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-, inner salt, 4-oxide, (7R,17Z)- 3,5,8-Trioxa-4-phosphahexacos-17-en-1-aminium, 4-hydroxy
• 3,5,8-Trioxa-4-phosphahexacos-17-en-1-aminium, 4-hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-, inner salt, 4-oxide, [R-(Z)]-
• Choline, hydroxide, dihydrogen phosphate, inner salt, ester with 1-palmito-2-olein, L- (8CI)
• ethanaminium, 2-[[hydroxy[[(2R)-3-[(1-oxohexadecyl)oxy]-2-[[(9Z)-1-oxo-9-octadecenyl]oxy]propyl]oxy]phosphinyl]oxy]-N,N,N-trimethyl-, inner salt

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8902	89.02%
Caco-2	-	0.8200	82.00%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Plasma membrane	0.7625	76.25%
OATP2B1 inhibitior	-	0.5730	57.30%
OATP1B1 inhibitior	+	0.8681	86.81%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9645	96.45%
P-glycoprotein inhibitior	+	0.7222	72.22%
P-glycoprotein substrate	-	0.5839	58.39%
CYP3A4 substrate	+	0.6147	61.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.7487	74.87%
CYP2C9 inhibition	-	0.8809	88.09%
CYP2C19 inhibition	-	0.8148	81.48%
CYP2D6 inhibition	-	0.8972	89.72%
CYP1A2 inhibition	-	0.8590	85.90%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9548	95.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.5439	54.39%
Eye corrosion	-	0.9162	91.62%
Eye irritation	-	0.8775	87.75%
Skin irritation	-	0.7656	76.56%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5544	55.44%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8111	81.11%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4728	47.28%
Acute Oral Toxicity (c)	III	0.4787	47.87%
Estrogen receptor binding	+	0.7906	79.06%
Androgen receptor binding	-	0.7878	78.78%
Thyroid receptor binding	-	0.5296	52.96%
Glucocorticoid receptor binding	+	0.6057	60.57%
Aromatase binding	-	0.4824	48.24%
PPAR gamma	+	0.5986	59.86%
Honey bee toxicity	-	0.8296	82.96%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.8424	84.24%
Fish aquatic toxicity	+	0.8546	85.46%

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	98.96%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.50%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.66%	98.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.31%	92.86%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.33%	92.08%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	92.40%	85.94%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.38%	95.17%
CHEMBL321	P14780	Matrix metalloproteinase 9	91.30%	92.12%
CHEMBL5255	O00206	Toll-like receptor 4	90.10%	92.50%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	86.83%	91.81%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.09%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.75%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.02%	96.95%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.84%	94.66%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.58%	94.33%
CHEMBL1781	P11387	DNA topoisomerase I	84.49%	97.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.25%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	83.84%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	82.82%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.70%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.16%	96.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.46%	100.00%

Plants that contains it

• Dioscorea oppositifolia

Cross-Links

• PubChem: 5497103
• LOTUS: LTS0188202
• wikiData: Q10860475