1-O-hexadecyl-2-hydroxy-sn-glycero-3-phosphocholine - ≥99% , CAS No.52691-62-0

CAS: 52691-62-0 Cat. No.: O130790 Molecular Weight: 481.647

GRADE & PURITY ≥99%

Synonyms

MFCD00042932 | HMS3648P08 | GPC(O-16:0/0:0) | [(2R)-3-hexadecoxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | 3,5,9-TRIOXA-4-PHOSPHAPENTACOSAN-1-AMINIUM, 4,7-DIHYDROXY-N,N,N-TRIMETHYL-, INNER SALT, 4-OXIDE, (7R)- | CHEBI:64496 | (2r)-3-(hexade

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Specifications

Synonyms

MFCD00042932 | HMS3648P08 | GPC(O-16:0/0:0) | [(2R)-3-hexadecoxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | 3, 5, 9-TRIOXA-4-PHOSPHAPENTACOSAN-1-AMINIUM, 4, 7-DIHYDROXY-N, N, N-TRIMETHYL-, INNER SALT, 4-OXIDE, (7R)- | CHEBI:64496 | (2r)-3-(hexade

Specifications & Purity

≥99%

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

• Pubchem Sid: 488188347
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488188347
• Canonical Smiles: CCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• IUPAC Name: [(2R)-3-hexadecoxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChIKey: VLBPIWYTPAXCFJ-XMMPIXPASA-N
• INCHI: 1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Molecular Weight: 481.647
• Reaxy-Rn: 4013354
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4013354&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: Monoalkylglycerophosphocholines
• Alternative Parents: Phosphocholines Glycerol ethers Dialkyl phosphates Tetraalkylammonium salts Secondary alcohols Dialkyl ethers Organopnictogen compounds Organic salts Organic oxides Hydrocarbon derivatives Amines
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Monoalkylglycerophosphocholine - Phosphocholine - Glycerol ether - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Quaternary ammonium salt - Tetraalkylammonium salt - Secondary alcohol - Ether - Dialkyl ether - Hydrocarbon derivative - Alcohol - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic salt - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as monoalkylglycerophosphocholines. These are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.
• External Descriptors: Monoalkylglycerophosphocholines

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(Human)

SK-MEL3 (228 Activities)

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SK-OV-3 (52876 Activities)

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XF498 (12972 Activities)

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A549 (127892 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 481.600 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 24
• Exact Mass: 481.353 Da
• Monoisotopic Mass: 481.353 Da
• Topological Polar Surface Area: 88.100 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 450.000
• 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. Jingyun Li, Siqi Zeng, Enyuan Zhang, Ling Chen, Jingbin Jiang, Jun Li.  (2024)  Spatial metabolomics to discover hypertrophic scar relevant metabolic alterations and potential therapeutic strategies: A preliminary study.  BIOORGANIC CHEMISTRY,      [PMID:39383811] [10.1016/j.bioorg.2024.107873]