1,2-Distearoyl-sn-glycero-3-phosphoethanolamine

Details

• Internal ID: 2aee5d4b-9d22-4b16-b294-1c21055d2f95
• Taxonomy: Lipids and lipid-like molecules > Glycerophospholipids > Glycerophosphoethanolamines > Phosphatidylethanolamines
• IUPAC Name: [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
• InChI: InChI=1S/C41H82NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39H,3-38,42H2,1-2H3,(H,45,46)/t39-/m1/s1
• InChI Key: LVNGJLRDBYCPGB-LDLOPFEMSA-N
• Popularity: 556 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₈₂NO₈P
• Molecular Weight: 748.10 g/mol
• Exact Mass: 747.57780557 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 12.40
• Atomic LogP (AlogP): 12.06
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 41

Synonyms

• 1069-79-0
• DSPE
• 1,2-Dioctadecanoyl-sn-glycero-3-phosphoethanolamine
• (R)-1,2-distearoylphosphatidylethanolamine
• L-beta,gamm
• 1,2-distearoyl-sn-glycero-3-phosphorylethanolamine
• Distearoyl phosphatidylethanolamine
• PE(18:0/18:0)
• (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl distearate
• 1G4B5265CQ
• L-alpha-Distearoylphosphatidylethanolamine
• 1,2-Distearoyl-sn-glycerophosphoethanolamine
• Stearin, 1,2-di-, 2-aminoethyl hydrogen phosphate, L-
• Octadecanoic acid, 1-[[[(2-aminoethoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, (R)-
• UNII-1G4B5265CQ
• MFCD00036777
• EINECS 213-963-9
• 1,2-distearoyl-rac-glycero-3-phosphoethanolamine
• DISTEAROYL CEPHALIN
• DSPE, L-
• DSPE, R-
• SCHEMBL25605
• 1,2-DSPE
• CHEBI:47766
• DTXSID601240990
• BCP11133
• LMGP02010097
• AKOS027322756
• GS-6360
• (R)-1-((((2-Aminoethoxy)hydroxyphosphinyl)oxy)methyl)ethane-1,2-diyl distearate
• [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
• 1,2-Distearoyl-sn-glycero-3-phosphoethan
• BP-23601
• HY-112530
• CS-0046318
• D4214
• H10394
• 1,2-Distearoyl L-|A,|A-Distearoyl-|A-cephalin
• J-001683
• 1,2-Distearoyl-sn-Glycero-3-Phosphatidylethanolamine
• Q60533035
• 1,2-Distearoyl-sn-glycero-3-phosphoethanolamine, >=99%
• 2-Aminoethyl (R)-2,3-Bis(octadecanoyloxy)propyl Hydrogen Phosphate
• (2-aminoethoxy)[(2R)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid
• (2R)-3-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyldistearate
• (2R)-3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}propane-1,2-diyl dioctadecanoate
• 3-SN-PHOSPHATIDYLETHANOLAMINE; 1,2-DIACYL-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
• (2R)-3-{[(R)-(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-(octadecanoyloxy)propyl octadecanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4891	48.91%
Caco-2	-	0.8222	82.22%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5808	58.08%
OATP2B1 inhibitior	-	0.5702	57.02%
OATP1B1 inhibitior	+	0.9006	90.06%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6633	66.33%
P-glycoprotein inhibitior	+	0.6815	68.15%
P-glycoprotein substrate	-	0.6315	63.15%
CYP3A4 substrate	+	0.5406	54.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7924	79.24%
CYP3A4 inhibition	-	0.6792	67.92%
CYP2C9 inhibition	-	0.8630	86.30%
CYP2C19 inhibition	-	0.7591	75.91%
CYP2D6 inhibition	-	0.8755	87.55%
CYP1A2 inhibition	-	0.7956	79.56%
CYP2C8 inhibition	-	0.6818	68.18%
CYP inhibitory promiscuity	-	0.9470	94.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6900	69.00%
Carcinogenicity (trinary)	Non-required	0.5972	59.72%
Eye corrosion	-	0.7843	78.43%
Eye irritation	-	0.8344	83.44%
Skin irritation	-	0.7894	78.94%
Skin corrosion	-	0.8064	80.64%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6090	60.90%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5518	55.18%
skin sensitisation	-	0.8366	83.66%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6166	61.66%
Acute Oral Toxicity (c)	III	0.5884	58.84%
Estrogen receptor binding	+	0.7495	74.95%
Androgen receptor binding	-	0.8352	83.52%
Thyroid receptor binding	-	0.5320	53.20%
Glucocorticoid receptor binding	-	0.5361	53.61%
Aromatase binding	+	0.5232	52.32%
PPAR gamma	+	0.5975	59.75%
Honey bee toxicity	-	0.8567	85.67%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.7469	74.69%
Fish aquatic toxicity	+	0.6824	68.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	99.75%	95.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	98.67%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.48%	99.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	97.06%	85.94%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	95.61%	94.01%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.09%	92.86%
CHEMBL299	P17252	Protein kinase C alpha	93.55%	98.03%
CHEMBL2885	P07451	Carbonic anhydrase III	92.52%	87.45%
CHEMBL5255	O00206	Toll-like receptor 4	91.85%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	90.28%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.70%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.89%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	85.73%	90.17%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.79%	80.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.02%	91.71%
CHEMBL1907	P15144	Aminopeptidase N	82.50%	93.31%
CHEMBL340	P08684	Cytochrome P450 3A4	82.08%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	81.65%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.62%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.09%	96.00%
CHEMBL2973	O75116	Rho-associated protein kinase 2	80.63%	96.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.12%	100.00%

Plants that contains it

• Hippophae rhamnoides

Cross-Links

• PubChem: 447078
• LOTUS: LTS0241176
• wikiData: Q60533035