1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine - ≥99% , CAS No.74389-69-8

CAS: 74389-69-8 Cat. No.: O130786 Molecular Weight: 551.736

GRADE & PURITY ≥99%

Synonyms

[(2R)-2-acetyloxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | (-)-1-O-octadeyl-2-O-acetyl-sn-glycerylphosphocholine | C18-02:0 PC, 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine, chloroform | PAF C18 | PC(O-18:0/2:0) | 1-octadecyl-2-ac

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A naturally occurring phospholipid involved in inflammation and other physiological processes.

Specifications

Synonyms

[(2R)-2-acetyloxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | (-)-1-O-octadeyl-2-O-acetyl-sn-glycerylphosphocholine | C18-02:0 PC, 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine, chloroform | PAF C18 | PC(O-18:0/2:0) | 1-octadecyl-2-ac

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

PAF C-18 is a naturally occurring phospholipid produced upon stimulation through two distinct pathways known as the de novo and remodeling pathways. PAF C-18 is less potent than PAF C-16 in the induction of platelet aggregation, but equipotent in activati

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
• IUPAC Name: [(2R)-2-acetyloxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: ZXCIEWBDUAPBJF-MUUNZHRXSA-N
• INCHI: 1S/C28H58NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h28H,6-26H2,1-5H3/t28-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
• Molecular Weight: 551.736
• Reaxy-Rn: 4727176
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4727176&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphocholines
        • Level5 1-alkyl,2-acylglycero-3-phosphocholines
          • Level6 1-alkyl,2-acetylglycero-3-phosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: 1-alkyl,2-acylglycero-3-phosphocholines
• Direct Parent: 1-alkyl,2-acetylglycero-3-phosphocholines
• Alternative Parents: Phosphocholines Glycerol ethers Dialkyl phosphates Tetraalkylammonium salts Carboxylic acid esters Monocarboxylic acids and derivatives Dialkyl ethers Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1-alkyl,2-acetylglycero-3-phosphocholine - Phosphocholine - Glycerol ether - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Tetraalkylammonium salt - Quaternary ammonium salt - Carboxylic acid ester - Carboxylic acid derivative - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Amine - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-alkyl,2-acetylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acetyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
• External Descriptors: 1-alkyl,2-acylglycerophosphocholines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Cavia porcellus (23802 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Oryctolagus cuniculus (11301 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 551.700 g/mol
• XLogP3: 7.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 28
• Exact Mass: 551.395 Da
• Monoisotopic Mass: 551.395 Da
• Topological Polar Surface Area: 94.100 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 575.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wanyi Chen, Binbin Chen, Xinjia Li, Gang Xu, Lirong Yang, Jianping Wu, Haoran Yu.  (2024)  Non-canonical amino acids uncover the significant impact of Tyr671 on Taq DNA polymerase catalytic activity.  FEBS Journal,      [PMID:38362811] [10.1111/febs.17091]