Phosphatidylethanolamine

Overview

DrugBank ID
DB04327
Type
Small Molecule
US Approved
NO
Other Approved
NO
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Phosphatidylethanolamine
DrugBank Accession Number
DB04327
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 749.0734
Monoisotopic: 748.585630149
Chemical Formula
C41H83NO8P
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhosphatidylinositol 3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN
substrate
Humans
UEndothelial protein C receptorNot AvailableHumans
UBacteriorhodopsinNot AvailableNostoc sp. (strain PCC 7120 / UTEX 2576)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphoethanolamines
Direct Parent
Phosphatidylethanolamines
Alternative Parents
Fatty acid esters / Dialkyl phosphates / Dicarboxylic acids and derivatives / Carboxylic acid esters / Amino acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aliphatic acyclic compound / Alkyl phosphate / Amine / Amino acid or derivatives / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Diacylglycero-3-phosphoethanolamine / Dialkyl phosphate / Dicarboxylic acid or derivatives
show 14 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
1,2-distearoylphosphatidylethanolaminium (CHEBI:44887)
Affected organisms
Not Available

Chemical Identifiers

UNII
7CMB6B4449
CAS number
Not Available
InChI Key
LVNGJLRDBYCPGB-KDXMTYKHSA-O
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)/p+1/t39-/m0/s1
IUPAC Name
(2-azaniumylethoxy)[(2S)-2,3-bis(octadecanoyloxy)propoxy]phosphinic acid
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[P@](O)(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC

References

General References
Not Available
KEGG Compound
C00350
PubChem Compound
17754130
PubChem Substance
46506543
ChemSpider
16744169
ChEBI
44887
PDBe Ligand
PEE
Wikipedia
Phosphatidylethanolamine

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.03e-05 mg/mLALOGPS
logP6.93ALOGPS
logP12.23Chemaxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.87Chemaxon
pKa (Strongest Basic)10Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area136 Å2Chemaxon
Rotatable Bond Count43Chemaxon
Refractivity220.7 m3·mol-1Chemaxon
Polarizability95.03 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9397
Blood Brain Barrier+0.7387
Caco-2 permeable-0.6216
P-glycoprotein substrateSubstrate0.5934
P-glycoprotein inhibitor INon-inhibitor0.7846
P-glycoprotein inhibitor IINon-inhibitor0.774
Renal organic cation transporterNon-inhibitor0.9162
CYP450 2C9 substrateNon-substrate0.8792
CYP450 2D6 substrateNon-substrate0.7957
CYP450 3A4 substrateNon-substrate0.59
CYP450 1A2 substrateNon-inhibitor0.8213
CYP450 2C9 inhibitorNon-inhibitor0.8515
CYP450 2D6 inhibitorNon-inhibitor0.8828
CYP450 2C19 inhibitorNon-inhibitor0.7636
CYP450 3A4 inhibitorNon-inhibitor0.7498
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9311
Ames testNon AMES toxic0.7582
CarcinogenicityNon-carcinogens0.6876
BiodegradationReady biodegradable0.6811
Rat acute toxicity2.1408 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7722
hERG inhibition (predictor II)Non-inhibitor0.6074
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-273.373
predicted
DeepCCS 1.0 (2019)
[M+H]+275.1979
predicted
DeepCCS 1.0 (2019)
[M+Na]+280.8039
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Dual-specificity protein phosphatase, dephosphorylating tyrosine-, serine- and threonine-phosphorylated proteins (PubMed:9187108, PubMed:9256433, PubMed:9616126). Also functions as a lipid phosphatase, removing the phosphate in the D3 position of the inositol ring of PtdIns(3,4,5)P3/phosphatidylinositol 3,4,5-trisphosphate, PtdIns(3,4)P2/phosphatidylinositol 3,4-diphosphate and PtdIns3P/phosphatidylinositol 3-phosphate with a preference for PtdIns(3,4,5)P3 (PubMed:16824732, PubMed:26504226, PubMed:9593664, PubMed:9811831). Furthermore, this enzyme can also act as a cytosolic inositol 3-phosphatase acting on Ins(1,3,4,5,6)P5/inositol 1,3,4,5,6 pentakisphosphate and possibly Ins(1,3,4,5)P4/1D-myo-inositol 1,3,4,5-tetrakisphosphate (PubMed:11418101, PubMed:15979280). Antagonizes the PI3K-AKT/PKB signaling pathway by dephosphorylating phosphoinositides and thereby modulating cell cycle progression and cell survival (PubMed:31492966, PubMed:37279284). The unphosphorylated form cooperates with MAGI2 to suppress AKT1 activation (PubMed:11707428). In motile cells, suppresses the formation of lateral pseudopods and thereby promotes cell polarization and directed movement (PubMed:22279049). Dephosphorylates tyrosine-phosphorylated focal adhesion kinase and inhibits cell migration and integrin-mediated cell spreading and focal adhesion formation (PubMed:22279049). Required for growth factor-induced epithelial cell migration; growth factor stimulation induces PTEN phosphorylation which changes its binding preference from the p85 regulatory subunit of the PI3K kinase complex to DLC1 and results in translocation of the PTEN-DLC1 complex to the posterior of migrating cells to promote RHOA activation (PubMed:26166433). Meanwhile, TNS3 switches binding preference from DLC1 to p85 and the TNS3-p85 complex translocates to the leading edge of migrating cells to activate RAC1 activation (PubMed:26166433). Plays a role as a key modulator of the AKT-mTOR signaling pathway controlling the tempo of the process of newborn neurons integration during adult neurogenesis, including correct neuron positioning, dendritic development and synapse formation (By similarity). Involved in the regulation of synaptic function in excitatory hippocampal synapses. Recruited to the postsynaptic membrane upon NMDA receptor activation, is required for the modulation of synaptic activity during plasticity. Enhancement of lipid phosphatase activity is able to drive depression of AMPA receptor-mediated synaptic responses, activity required for NMDA receptor-dependent long-term depression (LTD) (By similarity). May be a negative regulator of insulin signaling and glucose metabolism in adipose tissue. The nuclear monoubiquitinated form possesses greater apoptotic potential, whereas the cytoplasmic nonubiquitinated form induces less tumor suppressive ability (PubMed:10468583, PubMed:18716620)
Specific Function
anaphase-promoting complex binding
Gene Name
PTEN
Uniprot ID
P60484
Uniprot Name
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN
Molecular Weight
47165.92 Da
References
  1. Meuillet EJ, Mahadevan D, Berggren M, Coon A, Powis G: Thioredoxin-1 binds to the C2 domain of PTEN inhibiting PTEN's lipid phosphatase activity and membrane binding: a mechanism for the functional loss of PTEN's tumor suppressor activity. Arch Biochem Biophys. 2004 Sep 15;429(2):123-33. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Binds activated protein C. Enhances protein C activation by the thrombin-thrombomodulin complex; plays a role in the protein C pathway controlling blood coagulation
Specific Function
signaling receptor activity
Gene Name
PROCR
Uniprot ID
Q9UNN8
Uniprot Name
Endothelial protein C receptor
Molecular Weight
26671.245 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Nostoc sp. (strain PCC 7120 / UTEX 2576)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
monoatomic ion channel activity
Gene Name
Not Available
Uniprot ID
Q8YSC4
Uniprot Name
Bacteriorhodopsin
Molecular Weight
30190.99 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52