2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate

Details

• Internal ID: 38041eb3-de76-4ecc-91c5-23b021593193
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphates > Diacylglycerophosphates > 1,2-diacylglycerol-3-phosphates
• IUPAC Name: [(2R)-2-hexadecanoyloxy-3-phosphonooxypropyl] hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)O)OC(=O)CCCCCCCCCCCCCCC
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)OC(=O)CCCCCCCCCCCCCCC
• InChI: InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1
• InChI Key: PORPENFLTBBHSG-MGBGTMOVSA-N
• Popularity: 478 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₆₉O₈P
• Molecular Weight: 648.90 g/mol
• Exact Mass: 648.47300615 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 12.90
• Atomic LogP (AlogP): 10.51
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 34

Synonyms

• 7091-44-3
• Dipalmitoyl
• dipalmitoyl phosphatidic acid
• 1,2-Dipalmitoyl-3-sn-phosphatidic acid
• phosphatidic acid
• dipalmitoylphosphatidic acid
• 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid
• PA(16:0/16:0)
• L-alpha-Dipalmitoylphosphatidic acid
• Phosphatidic acid(32:0)
• [(2R)-2-hexadecanoyloxy-3-phosphonooxypropyl] hexadecanoate
• Phosphatidic acid(16:0/16:0)
• 2-(HEXADECANOYLOXY)-1-[(PHOSPHONOOXY)METHYL]ETHYL HEXADECANOATE
• L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID
• 1,2-dihexadecanoyl-sn-glycero-3-phosphate
• Dipalmitoyl-L-alpha-phosphatidic acid
• 1,2-dihexadecanoyl-sn-glycerol-3-phosphate
• Palmitin, 1,2-di-, dihydrogen phosphate, L-
• 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid
• (2R)-3-(phosphonooxy)propane-1,2-diyl dihexadecanoate
• Hexadecanoic acid, 1-[(phosphonooxy)methyl]-1,2-ethanediyl ester, (R)-
• PA(32:0)
• Dipalmitoylphosphatidate
• L-a-Dipalmitoylphosphatidate
• SCHEMBL44215
• Dipalmitoyl-L-a-phosphatidate
• L-a-Dipalmitoyl-phosphatidate
• L-alpha-Dipalmitoylphosphatidate
• L-a-Dipalmitoylphosphatidic acid
• CHEBI:73246
• Dipalmitoyl-L-alpha-phosphatidate
• L-alpha-Dipalmitoyl-phosphatidate
• Dipalmitoyl-L-a-phosphatidic acid
• L-a-Dipalmitoyl-phosphatidic acid
• PORPENFLTBBHSG-MGBGTMOVSA-N
• DTXSID101301555
• 1,2-Dipalmitoyl-3-sn-phosphatidate
• L-alpha-Dipalmitoyl-phosphatidic acid
• LMGP10010027
• AKOS040732217
• 16:0 PA
• 1,2-dihexadecanoyl-rac-phosphatidic acid
• 1,2-dipalmitoyl-sn-glycerol-3-phosphate
• PD101874
• 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate
• HY-113437
• CS-0059528
• 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate
• Palmitin, 1,2-di-, dihydrogen phosphate, L- (8CI)
• Q27140395
• Hexadecanoic acid, 1-[(phosphonooxy)methyl]-1,2-ethanediyl ester,(R)-
• Hexadecanoic acid, (1R)-1-[(phosphonooxy)methyl]-1,2-ethanediyl ester(9CI)
• hexadecanoic acid, (1R)-2-[(1-oxohexadecyl)oxy]-1-[(phosphonooxy)methyl]ethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6222	62.22%
Caco-2	-	0.7907	79.07%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7998	79.98%
OATP2B1 inhibitior	-	0.7140	71.40%
OATP1B1 inhibitior	+	0.8946	89.46%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8420	84.20%
P-glycoprotein inhibitior	+	0.6222	62.22%
P-glycoprotein substrate	-	0.7878	78.78%
CYP3A4 substrate	+	0.5095	50.95%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.9161	91.61%
CYP2C9 inhibition	-	0.8731	87.31%
CYP2C19 inhibition	-	0.8381	83.81%
CYP2D6 inhibition	-	0.9024	90.24%
CYP1A2 inhibition	-	0.8631	86.31%
CYP2C8 inhibition	-	0.8507	85.07%
CYP inhibitory promiscuity	-	0.9613	96.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.6107	61.07%
Eye corrosion	+	0.5655	56.55%
Eye irritation	-	0.7644	76.44%
Skin irritation	-	0.7569	75.69%
Skin corrosion	+	0.6464	64.64%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4422	44.22%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5699	56.99%
skin sensitisation	-	0.8502	85.02%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.8000	80.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6669	66.69%
Acute Oral Toxicity (c)	III	0.6019	60.19%
Estrogen receptor binding	+	0.8248	82.48%
Androgen receptor binding	-	0.8279	82.79%
Thyroid receptor binding	-	0.5826	58.26%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5916	59.16%
PPAR gamma	+	0.6536	65.36%
Honey bee toxicity	-	0.8415	84.15%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.7704	77.04%
Fish aquatic toxicity	+	0.9672	96.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3819	Q92633	Lysophosphatidic acid receptor Edg-2	407 nM; 221 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL3250	Q9UBY5	Lysophosphatidic acid receptor Edg-7	119 nM; 39 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	707.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	99.13%	97.29%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.61%	95.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	96.75%	85.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.53%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.29%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.49%	92.86%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	93.21%	94.01%
CHEMBL299	P17252	Protein kinase C alpha	92.83%	98.03%
CHEMBL5255	O00206	Toll-like receptor 4	92.09%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.46%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.33%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.35%	91.71%
CHEMBL4333	P21453	Sphingosine 1-phosphate receptor Edg-1	87.23%	96.99%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.19%	91.81%
CHEMBL1907	P15144	Aminopeptidase N	83.86%	93.31%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	83.38%	92.08%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.37%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.29%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	82.28%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.77%	93.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.37%	100.00%

Plants that contains it

• Amaranthus blitum subsp. oleraceus
• Ferula tenuisecta
• Murraya koenigii
• Pyracantha coccinea
• Ruta graveolens

Cross-Links

• PubChem: 446066
• LOTUS: LTS0190394
• wikiData: Q27140395