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

Details

• Internal ID: dac7b78b-4774-4d00-9dca-60fe5e1c58a9
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphocholines > Lysophosphatidylcholines > 1-acyl-sn-glycero-3-phosphocholines
• IUPAC Name: [(2R)-3-[(Z)-hexadec-9-enoyl]oxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• SMILES (Canonical): CCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• SMILES (Isomeric): CCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• InChI: InChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h10-11,23,26H,5-9,12-22H2,1-4H3/b11-10-/t23-/m1/s1
• InChI Key: LFUDDCMNKWEORN-ZXEGGCGDSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₈NO₇P
• Molecular Weight: 493.60 g/mol
• Exact Mass: 493.31683987 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.36
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 22

Synonyms

• 1-palmitoleoyl-glycerophosphocholine
• CHEBI:73851
• 1-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine
• [(2R)-3-[(Z)-hexadec-9-enoyl]oxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• 1-((9Z)-hexadecenoyl)-sn-glycero-3-phosphocholine
• ((2R)-3-((Z)-hexadec-9-enoyl)oxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
• RefChem:1054576
• 76790-27-7
• PC(16:1(9Z)/0:0)
• LysoPC(16:1(9Z))
• LysoPC(16:1(9Z)/0:0)
• 1-palmitoleoyl-glycero-3-phosphocholine
• 1-palmitoleoyl-sn-glycero-3-phosphocholine
• LPC(16:1/0:0)
• (R,Z)-3-(Hexadec-9-enoyloxy)-2-hydroxypropyl (2-(trimethylammonio)ethyl) phosphate
• LPC 16:1
• LPC(16:1)
• (7R,18Z)-4,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphapentacos-18-en-1-aminium inner salt 4-oxide
• 1-palmitoleoyl-GPC
• lysoPC a C16:1
• T5T3TC2ZQQ
• 1-16:1-lysoPC
• LysoPC(16:1)
• Lysophosphatidylcholine(16:1)
• orb2564732
• CHEMBL5431567
• LyPC(16:1)
• LysoPC(16:1/0:0)
• SCHEMBL29426378
• LysoPC(16:1n7/0:0)
• LysoPC(16:1w7/0:0)
• DTXSID701108020
• 1-16:1-2-lysophosphatidylcholine
• LyPC(16:1n7/0:0)
• LyPC(16:1w7/0:0)
• LysoPC 16:1(9Z)/0:0
• LMGP01050022
• LyPC(16:1/0:0)
• Lysophosphatidylcholine(16:1/0:0)
• GPC(16:1(9Z))
• LPC(16:1n7/0:0)
• LPC(16:1w7/0:0)
• Lysophosphatidylcholine(16:1n7/0:0)
• Lysophosphatidylcholine(16:1w7/0:0)
• lysophosphatidylcholine(16:1(9Z)/0:0)
• LPC 16:1(9Z)/0:0
• CS-0062322
• LPC(16:1(9Z)/0:0)
• PC 16:1(9Z)/0:0
• Q27144179
• (2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl 2-(trimethylammonio)ethyl phosphate
• 3,5,9-Trioxa-4-phosphapentacos-18-en-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide, (7R,18Z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9019	90.19%
Caco-2	-	0.7472	74.72%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Plasma membrane	0.6650	66.50%
OATP2B1 inhibitior	-	0.8585	85.85%
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	+	0.7074	70.74%
P-glycoprotein inhibitior	-	0.4881	48.81%
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	-	0.8477	84.77%
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	-	0.5142	51.42%
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	+	0.7473	74.73%
Androgen receptor binding	-	0.7064	70.64%
Thyroid receptor binding	-	0.5169	51.69%
Glucocorticoid receptor binding	-	0.5604	56.04%
Aromatase binding	-	0.4909	49.09%
PPAR gamma	-	0.5054	50.54%
Honey bee toxicity	-	0.8560	85.60%
Biodegradation	-	0.5250	52.50%
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: 24779461
• LOTUS: LTS0101466
• wikiData: Q27144179