Explore a selection of our essential drug information below, or:
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
Structure for (2R)-2-Acetamido-3-(octadecyloxy)propyl 2-(methylsulfanyl)ethyl hydrogen phosphate (DB04112)
- Weight
- Average: 539.749
Monoisotopic: 539.340945667 - Chemical Formula
- C26H54NO6PS
- Synonyms
- 1-Octadecyl-2-acetamido-2-deoxy-SN-glycerol-3-phosphoethylmethyl sulfide
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPhospholipase A2, membrane associated Not Available Humans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- External Links
- PubChem Compound
- 5288635
- PubChem Substance
- 46506883
- ChemSpider
- 4450758
- ZINC
- ZINC000014881051
- PDBe Ligand
- INB
- PDB Entries
- 1ayp
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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
Property Value Source Water Solubility 0.000349 mg/mL ALOGPS logP 6.11 ALOGPS logP 7.11 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 1.92 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 94.09 Å2 Chemaxon Rotatable Bond Count 27 Chemaxon Refractivity 147.14 m3·mol-1 Chemaxon Polarizability 65.12 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7114 Blood Brain Barrier + 0.9087 Caco-2 permeable - 0.6319 P-glycoprotein substrate Substrate 0.5192 P-glycoprotein inhibitor I Non-inhibitor 0.6232 P-glycoprotein inhibitor II Non-inhibitor 0.8781 Renal organic cation transporter Non-inhibitor 0.9514 CYP450 2C9 substrate Non-substrate 0.8357 CYP450 2D6 substrate Non-substrate 0.8093 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.827 CYP450 2C9 inhibitor Non-inhibitor 0.8166 CYP450 2D6 inhibitor Non-inhibitor 0.9045 CYP450 2C19 inhibitor Non-inhibitor 0.7071 CYP450 3A4 inhibitor Non-inhibitor 0.7477 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9577 Ames test Non AMES toxic 0.6566 Carcinogenicity Non-carcinogens 0.7883 Biodegradation Not ready biodegradable 0.9207 Rat acute toxicity 2.5871 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9256 hERG inhibition (predictor II) Non-inhibitor 0.7726
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 207.49193 predictedDeepCCS 1.0 (2019) [M+H]+ 210.04225 predictedDeepCCS 1.0 (2019) [M+Na]+ 217.3664 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secretory calcium-dependent phospholipase A2 that primarily targets extracellular phospholipids with implications in host antimicrobial defense, inflammatory response and tissue regeneration (PubMed:10455175, PubMed:10681567, PubMed:2925633). Hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) with preference for phosphatidylethanolamines and phosphatidylglycerols over phosphatidylcholines (PubMed:10455175, PubMed:10681567). Contributes to lipid remodeling of cellular membranes and generation of lipid mediators involved in pathogen clearance. Displays bactericidal activity against Gram-positive bacteria by directly hydrolyzing phospholipids of the bacterial membrane (PubMed:10358193, PubMed:11694541). Upon sterile inflammation, targets membrane phospholipids of extracellular mitochondria released from activated platelets, generating free unsaturated fatty acids such as arachidonate that is used by neighboring leukocytes to synthesize inflammatory eicosanoids such as leukotrienes. Simultaneously, by compromising mitochondrial membrane integrity, promotes the release in circulation of potent damage-associated molecular pattern molecules that activate the innate immune response (PubMed:25082876). Plays a stem cell regulator role in the intestinal crypt. Within intracellular compartment mediates Paneth cell differentiation and its stem cell supporting functions by inhibiting Wnt signaling pathway in intestinal stem cell (ICS). Secreted in the intestinal lumen upon inflammation, acts in an autocrine way and promotes prostaglandin E2 synthesis that stimulates Wnt signaling pathway in ICS cells and tissue regeneration (By similarity). May play a role in the biosynthesis of N-acyl ethanolamines that regulate energy metabolism and inflammation. Hydrolyzes N-acyl phosphatidylethanolamines to N-acyl lysophosphatidylethanolamines, which are further cleaved by a lysophospholipase D to release N-acyl ethanolamines (PubMed:14998370). Independent of its catalytic activity, acts as a ligand for integrins (PubMed:18635536, PubMed:25398877). Binds to and activates integrins ITGAV:ITGB3, ITGA4:ITGB1 and ITGA5:ITGB1 (PubMed:18635536, PubMed:25398877). Binds to a site (site 2) which is distinct from the classical ligand-binding site (site 1) and induces integrin conformational changes and enhanced ligand binding to site 1 (PubMed:25398877). Induces cell proliferation in an integrin-dependent manner (PubMed:18635536)
- Specific Function
- Calcium ion binding
- Gene Name
- PLA2G2A
- Uniprot ID
- P14555
- Uniprot Name
- Phospholipase A2, membrane associated
- Molecular Weight
- 16082.525 Da
References
Drug created at June 13, 2005 13:24 / Updated at July 11, 2020 03:42