1-O-Octyl-2-Heptylphosphonyl-Sn-Glycero-3-Phosphoethanolamine

Identification

Name
1-O-Octyl-2-Heptylphosphonyl-Sn-Glycero-3-Phosphoethanolamine
Accession Number
DB03565  (EXPT01580)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 489.5207
Monoisotopic: 489.262040445
Chemical Formula
C20H45NO8P2
InChI Key
RCCNUBYROFOKAU-HXUWFJFHSA-N
InChI
InChI=1S/C20H45NO8P2/c1-3-5-7-9-10-12-15-26-18-20(19-28-31(24,25)27-16-14-21)29-30(22,23)17-13-11-8-6-4-2/h20H,3-19,21H2,1-2H3,(H,22,23)(H,24,25)/t20-/m1/s1
IUPAC Name
{[(2R)-1-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-3-(octyloxy)propan-2-yl]oxy}(heptyl)phosphinic acid
SMILES
[H][[email protected]@](COCCCCCCCC)(COP(O)(=O)OCCN)OP(O)(=O)CCCCCCC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhospholipase A2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
129148
PubChem Substance
46504601
ChemSpider
114411
BindingDB
50366475
ChEMBL
CHEMBL1159973
HET
GEL
PDB Entries
1mkv / 1pob / 1poc / 1poe

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.806 mg/mLALOGPS
logP2.7ALOGPS
logP2.34ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.75ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area137.54 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity122.05 m3·mol-1ChemAxon
Polarizability54.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7532
Blood Brain Barrier+0.7818
Caco-2 permeable-0.6122
P-glycoprotein substrateSubstrate0.6787
P-glycoprotein inhibitor INon-inhibitor0.6193
P-glycoprotein inhibitor IINon-inhibitor0.8686
Renal organic cation transporterNon-inhibitor0.8948
CYP450 2C9 substrateNon-substrate0.9106
CYP450 2D6 substrateNon-substrate0.7645
CYP450 3A4 substrateNon-substrate0.5886
CYP450 1A2 substrateNon-inhibitor0.8158
CYP450 2C9 inhibitorNon-inhibitor0.8464
CYP450 2D6 inhibitorNon-inhibitor0.8876
CYP450 2C19 inhibitorNon-inhibitor0.7865
CYP450 3A4 inhibitorNon-inhibitor0.7044
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9665
Ames testNon AMES toxic0.7244
CarcinogenicityNon-carcinogens0.6018
BiodegradationNot ready biodegradable0.7533
Rat acute toxicity2.2540 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6104
hERG inhibition (predictor II)Non-inhibitor0.5594
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as glycerophosphoethanolamines. These are glycerolipids characterized by an ethanolamine ester of glycerophosphoric acid. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphoethanolamines
Direct Parent
Glycerophosphoethanolamines
Alternative Parents
Glycerophosphonolipids / Phosphoethanolamines / Glycerol ethers / Dialkyl phosphates / Phosphonic acid esters / Organic phosphonic acids / Dialkyl ethers / Organopnictogen compounds / Organophosphorus compounds / Organic oxides
show 2 more
Substituents
Sn-glycero-3-phosphoethanolamine / Glycerophosphonolipid / Phosphoethanolamine / Glycerol ether / Dialkyl phosphate / Organic phosphoric acid derivative / Phosphoric acid ester / Phosphonic acid ester / Alkyl phosphate / Organophosphonic acid derivative
show 15 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
Gene Name
PLA2G1B
Uniprot ID
P04054
Uniprot Name
Phospholipase A2
Molecular Weight
16359.535 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:15