N-Palmitoyl-D-sphingosine - ≥99% , CAS No.24696-26-2

CAS: 24696-26-2 Cat. No.: N130620 Molecular Weight: 537.901 EC Number: 640-541-5

GRADE & PURITY ≥99%

Synonyms

N-Palmitoylsphingosine | N-palmitoyl-sphingosine | Hexadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]- | N-Palmitoyl-D-erythro-sphingosine;N-Hexadecanoyl-D-erythro-sphingosine;N-Palmitoyl ceramide | BDBM50289523 | N-(hexadecanoyl)-sp

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Ceramide comprise sphingosine and fatty acid and belongs to the sphingolipids family

• as an internal standard in the chromatography with negative ion electrospray ionization coupled to tandem mass spectrometry for myocardial ceramide quantification

• as an internal standard for the ceramide quantification from rat samples using liquid chromatography-mass spectrometry

• to test its effect on mitochondrial stress response in worms

Specifications

Synonyms

N-Palmitoylsphingosine | N-palmitoyl-sphingosine | Hexadecanamide, N-[(1S, 2R, 3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]- | N-Palmitoyl-D-erythro-sphingosine;N-Hexadecanoyl-D-erythro-sphingosine;N-Palmitoyl ceramide | BDBM50289523 | N-(hexadecanoyl)-sp

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

C16 Ceramide levels are elevated in chronic alcohol-related liver disease (ALD). In general, ceramide inhibits mitochondrial function and insulin signaling. They are essential component of cell membrane and are involved in lipid raft formation. C16 cerami

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Action Type

ACTIVATOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504763468
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763468
• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• IUPAC Name: N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• InChIKey: YDNKGFDKKRUKPY-TURZORIXSA-N
• INCHI: 1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Molecular Weight: 537.901
• Reaxy-Rn: 29799713
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29799713&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Sphingolipids
      • Subclass Ceramides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Sphingolipids
• Subclass: Ceramides
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain ceramides
• Alternative Parents: N-acyl amines Secondary carboxylic acid amides Secondary alcohols Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain ceramide - Fatty amide - N-acyl-amine - Fatty acyl - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid derivative - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alcohol - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
• External Descriptors: N-acylsphingosines (ceramides)

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)

CETP Tchem Cholesteryl ester transfer protein (2422 Activities)

Discover Target: CETP

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

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

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

Associated Targets(non-human)

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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

Ulva (10 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

• Solubility: Soluble in DMF at 0.15mg/ml
• Sensitivity: Hygroscopic; sensitive to air
• Melt Point(°C): 98 - 99°C
• Molecular Weight: 537.900 g/mol
• XLogP3: 12.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 30
• Exact Mass: 537.512 Da
• Monoisotopic Mass: 537.512 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 508.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1