N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide

• ChemBase ID: 155076
• Molecular Formular: C20H41NO4
• Molecular Mass: 359.54384
• Monoisotopic Mass: 359.3035588
• SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)NC(=O)C)O)O
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@@H](NC(=O)C)CO)O)O
• InChI: InChI=1S/C20H41NO4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-19(24)20(25)18(16-22)21-17(2)23/h18-20,22,24-25H,3-16H2,1-2H3,(H,21,23)/t18-,19+,20-/m0/s1
• InChIKey: SZUJJDLBXJCDNT-ZCNNSNEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide
• IUPAC Traditional name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide
• Synonyms: Phytoceramide C2

Database IDs

• MDL Number: MFCD02686954
• PubChem SID: 24893024; 162249214
• PubChem CID: 9798946

CALCULATED PROPERTIES

• Acid pKa: 13.239481
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 3.516537
• LogD (pH = 7.4): 3.5165367
• Log P: 3.5165372
• Molar Refractivity: 101.7347 cm^3
• Polarizability: 40.63331 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >25 mg/mL (with warming); ethanol: >25 mg/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98% (TLC)
• Empirical Formula (Hill Notation): C20H41NO4

DETAILS

Sigma Aldrich - C8105

Biochem/physiol Actions
Yeast growth inhibitor and ceramide-activated protein phosphatase (CAPP) activator.