NAV

(2R)-2-Acetamido-3-(octadecyloxy)propyl 2-(methylsulfanyl)ethyl hydrogen phosphate

Identification

Generic Name
(2R)-2-Acetamido-3-(octadecyloxy)propyl 2-(methylsulfanyl)ethyl hydrogen phosphate
DrugBank Accession Number
DB04112
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 539.749
Monoisotopic: 539.340945667
Chemical Formula
C26H54NO6PS
Synonyms
  • 1-Octadecyl-2-acetamido-2-deoxy-SN-glycerol-3-phosphoethylmethyl sulfide
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhospholipase A2, membrane associatedNot 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phosphoethanolamines. These are compounds containing a phosphate linked to the second carbon of an ethanolamine.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphoric acids and derivatives
Sub Class
Phosphate esters
Direct Parent
Phosphoethanolamines
Alternative Parents
Dialkyl phosphates / Acetamides / Secondary carboxylic acid amides / Sulfenyl compounds / Dialkylthioethers / Dialkyl ethers / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetamide / Aliphatic acyclic compound / Alkyl phosphate / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether / Dialkyl phosphate / Dialkylthioether / Ether
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZULTVWFLRZJENJ-AREMUKBSSA-N
InChI
InChI=1S/C26H54NO6PS/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-31-23-26(27-25(2)28)24-33-34(29,30)32-21-22-35-3/h26H,4-24H2,1-3H3,(H,27,28)(H,29,30)/t26-/m1/s1
IUPAC Name
[(2R)-2-acetamido-3-(octadecyloxy)propoxy][2-(methylsulfanyl)ethoxy]phosphinic acid
SMILES
[H]N([C@H](COCCCCCCCCCCCCCCCCCC)COP(O)(=O)OCCSC)C(C)=O

References

General References
Not Available
PubChem Compound
5288635
PubChem Substance
46506883
ChemSpider
4450758
ZINC
ZINC000014881051
PDBe Ligand
INB
PDB Entries
1ayp

Clinical Trials

Clinical Trials
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 Solubility0.000349 mg/mLALOGPS
logP6.11ALOGPS
logP7.11Chemaxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.92Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area94.09 Å2Chemaxon
Rotatable Bond Count27Chemaxon
Refractivity147.14 m3·mol-1Chemaxon
Polarizability65.12 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7114
Blood Brain Barrier+0.9087
Caco-2 permeable-0.6319
P-glycoprotein substrateSubstrate0.5192
P-glycoprotein inhibitor INon-inhibitor0.6232
P-glycoprotein inhibitor IINon-inhibitor0.8781
Renal organic cation transporterNon-inhibitor0.9514
CYP450 2C9 substrateNon-substrate0.8357
CYP450 2D6 substrateNon-substrate0.8093
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.827
CYP450 2C9 inhibitorNon-inhibitor0.8166
CYP450 2D6 inhibitorNon-inhibitor0.9045
CYP450 2C19 inhibitorNon-inhibitor0.7071
CYP450 3A4 inhibitorNon-inhibitor0.7477
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9577
Ames testNon AMES toxic0.6566
CarcinogenicityNon-carcinogens0.7883
BiodegradationNot ready biodegradable0.9207
Rat acute toxicity2.5871 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9256
hERG inhibition (predictor II)Non-inhibitor0.7726
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/MSsplash10-00kf-5405290000-d64040276c9968e23711
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000190000-505f648f7c482863e6b4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-7200960000-d1b2cec3b0031c4153d9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-2509400000-53cc065c5562061b2970
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-9500000000-7a6f88a5a8924379f53f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xs-1901100000-33c88ea678f7020253ce
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.49193
predicted
DeepCCS 1.0 (2019)
[M+H]+210.04225
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.3664
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Phospholipase A2, membrane associated
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipid binding
Specific Function
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-ph...
Gene Name
PLA2G2A
Uniprot ID
P14555
Uniprot Name
Phospholipase A2, membrane associated
Molecular Weight
16082.525 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]

Drug created at June 13, 2005 13:24 / Updated at July 11, 2020 03:42