1-palmitoyl-2-(5'-oxo-valeroyl)-sn-glycero-3-phosphocholine(POVPC) - ≥99% , CAS No.121324-31-0

CAS: 121324-31-0 Cat. No.: P130753 Molecular Weight: 593.73

GRADE & PURITY ≥99%

Synonyms

3,5,9-Trioxa-4-phosphapentacosan-1-aminium,7-[(1,5-dioxopentyl)oxy]-4-hydroxy-N,N,N-trimethyl-10-oxo-,innersalt,4-oxide,(7R)- | HMS3648A15 | [(2R)-3-hexadecanoyloxy-2-(5-oxopentanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate | 1-palmitoyl-2-(5-oxov

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine (POVPC) is a derivative of oxidized Low density lipoprotein (oxLDL), a proinflammatory lipid present in atherosclerotic lesions

1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine (POVPC) has been used:
• to study its effects on endothelial function and vasodilation
• as a ligand for LRP6 in bone marrow mesenchymal stromal cells (MSCs)
• as a oxidized lipid to study if membrane status at different degrees of lipid peroxidation is involved in oxidative stress toleranc

Specifications

Synonyms

3, 5, 9-Trioxa-4-phosphapentacosan-1-aminium, 7-[(1, 5-dioxopentyl)oxy]-4-hydroxy-N, N, N-trimethyl-10-oxo-, innersalt, 4-oxide, (7R)- | HMS3648A15 | [(2R)-3-hexadecanoyloxy-2-(5-oxopentanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate | 1-palmitoyl-2-(5-oxov

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine (POVPC) affects endothelial function by hindering activity of endothelial nitric oxide synthase and stimulating endothelial cell apoptosis. It is implicated in the development of atherosclerosis

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: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCC=O
• IUPAC Name: [(2R)-3-hexadecanoyloxy-2-(5-oxopentanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: RKIDALSACBQVTN-HHHXNRCGSA-N
• INCHI: 1S/C29H56NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-28(32)36-25-27(39-29(33)21-18-19-23-31)26-38-40(34,35)37-24-22-30(2,3)4/h23,27H,5-22,24-26H2,1-4H3/t27-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCC=O
• Molecular Weight: 593.73
• Reaxy-Rn: 27151284
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27151284&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Glycerophospholipids
      • Subclass Glycerophosphocholines

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Glycerophospholipids
• Subclass: Glycerophosphocholines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphatidylcholines
• Alternative Parents: Phosphocholines Fatty acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Tetraalkylammonium salts Alpha-hydrogen aldehydes Carboxylic acid esters Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Diacylglycero-3-phosphocholine - Phosphocholine - Fatty acid ester - Dialkyl phosphate - Dicarboxylic acid or derivatives - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Fatty acyl - Tetraalkylammonium salt - Quaternary ammonium salt - Alpha-hydrogen aldehyde - Carboxylic acid ester - Carboxylic acid derivative - Amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aldehyde - Organic oxygen compound - Organopnictogen compound - Organic oxide - Organic salt - Carbonyl group - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
• External Descriptors: Oxidized glycerophosphocholines

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

Chemical and Physical Properties

• Molecular Weight: 593.700 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 30
• Exact Mass: 593.369 Da
• Monoisotopic Mass: 593.369 Da
• Topological Polar Surface Area: 128.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 704.000
• 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. Han Zhiyang, Hu Haidi, Yin MingZhu, Lin Yu, Yan Yan, Han Peng, Liu Bing, Jing Bao.  (2023)  HOXA1 participates in VSMC-to-macrophage-like cell transformation via regulation of NF-κB p65 and KLF4: a potential mechanism of atherosclerosis pathogenesis.  MOLECULAR MEDICINE,  29  (1): (1-19).  [PMID:37528397] [10.1186/s10020-023-00685-8]