NAV

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

Identification

Generic Name
1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine
DrugBank Accession Number
DB01728
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 691.972
Monoisotopic: 691.515205345
Chemical Formula
C37H74NO8P
Synonyms
  • 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine
  • 2-aminoethyl (2R)-2,3-bis(hexadecanoyloxy)propyl hydrogen phosphate
  • 2-aminoethyl (2R)-2,3-bis(palmitoyloxy)propyl hydrogen phosphate
  • Dipalmitoyl phosphatidylethanolamine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URhodopsinNot AvailableHumans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Phosphoethanolamines / Fatty acid esters / Dialkyl phosphates / Dicarboxylic acids and derivatives / Carboxylic acid esters / Amino acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
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-diacyl-sn-glycero-3-phosphoethanolamine (CHEBI:73127) / Diacylglycerophosphoethanolamines (LMGP02010037)
Affected organisms
Not Available

Chemical Identifiers

UNII
4FWH120Z1Z
CAS number
923-61-5
InChI Key
SLKDGVPOSSLUAI-PGUFJCEWSA-N
InChI
InChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1
IUPAC Name
(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC

References

General References
Not Available
Human Metabolome Database
HMDB0008923
PubChem Compound
445468
PubChem Substance
46505763
ChemSpider
393103
ChEBI
73005
ZINC
ZINC000032793824
PDBe Ligand
PEF
PDB Entries
1eys / 1gzm / 1kb9 / 1yp0 / 1zdt / 2qgu / 2x72 / 3c9l / 3wmm / 4rhp …
show 32 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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 Solubility9.45e-05 mg/mLALOGPS
logP8.08ALOGPS
logP10.45Chemaxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.87Chemaxon
pKa (Strongest Basic)10Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area134.38 Å2Chemaxon
Rotatable Bond Count39Chemaxon
Refractivity191 m3·mol-1Chemaxon
Polarizability85.59 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5521
Blood Brain Barrier+0.7335
Caco-2 permeable-0.6391
P-glycoprotein substrateSubstrate0.5946
P-glycoprotein inhibitor INon-inhibitor0.7401
P-glycoprotein inhibitor IINon-inhibitor0.8654
Renal organic cation transporterNon-inhibitor0.9128
CYP450 2C9 substrateNon-substrate0.9082
CYP450 2D6 substrateNon-substrate0.792
CYP450 3A4 substrateNon-substrate0.6088
CYP450 1A2 substrateNon-inhibitor0.7956
CYP450 2C9 inhibitorNon-inhibitor0.863
CYP450 2D6 inhibitorNon-inhibitor0.8755
CYP450 2C19 inhibitorNon-inhibitor0.7591
CYP450 3A4 inhibitorNon-inhibitor0.6792
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.947
Ames testNon AMES toxic0.7619
CarcinogenicityNon-carcinogens0.6597
BiodegradationNot ready biodegradable0.6926
Rat acute toxicity2.0899 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8748
hERG inhibition (predictor II)Non-inhibitor0.6491
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
LC-MS/MS Spectrum - LC-ESI-Ion Trap , NegativeLC-MS/MSsplash10-0a4i-0090100000-78393dc4e019ebd83091
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9600045000-17878dc7039524402655
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0000009000-e861d73c64527ea6fcb2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-2370819000-1c804efcd0108cc3d035
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfs-9400073000-2867636fadc4481a4eaf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-4390600000-0f8f6a1a044038e74d27
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-2910100000-d5b8514bd5545f7ae58e
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-351.7346598
predicted
DarkChem Lite v0.1.0
[M-H]-255.50652
predicted
DeepCCS 1.0 (2019)
[M+H]+352.3308598
predicted
DarkChem Lite v0.1.0
[M+H]+257.86453
predicted
DeepCCS 1.0 (2019)
[M+Na]+352.6411598
predicted
DarkChem Lite v0.1.0
[M+Na]+263.9581
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Rhodopsin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Photoreceptor activity
Specific Function
Photoreceptor required for image-forming vision at low light intensity. Required for photoreceptor cell viability after birth. Light-induced isomerization of 11-cis to all-trans retinal triggers a ...
Gene Name
RHO
Uniprot ID
P08100
Uniprot Name
Rhodopsin
Molecular Weight
38892.335 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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51