2-hexadecanamidoacetic acid

• ChemBase ID: 3118
• Molecular Formular: C18H35NO3
• Molecular Mass: 313.4754
• Monoisotopic Mass: 313.26169399
• SMILES: C(=O)(O)CNC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCC(=O)O
• InChI: InChI=1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)
• InChIKey: KVTFEOAKFFQCCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hexadecanamidoacetic acid
• IUPAC Traditional name: N-palmitoyl glycine
• Synonyms: N-Hexadecanoylglycine; Hexadecanoylaminoacetic acid; N-palmitoyl glycine; PalGly

Database IDs

• CAS Number: 2441-41-0
• MDL Number: MFCD00153471
• PubChem SID: 160966562; 46505498
• PubChem CID: 151008

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.0466223
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6865194
• LogD (pH = 7.4): 2.0195756
• Log P: 5.1512995
• Molar Refractivity: 89.8871 cm^3
• Polarizability: 35.599537 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.18
• LOG S: -5.65
• Solubility (Water): 7.08e-04 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H35NO3

DETAILS

DrugBank - DB03440

Drug information: experimental

Sigma Aldrich - P0064

Biochem/physiol Actions
PalGly is an endogenous signaling lipid that modulates calcium influx and nitric oxide production. PalGly inhibits heat-evoked firing of wide dynamic range (WDR) neurons, activates calcium influx in DRG cells and stimulates NO production. Preliminary studies suggest its signaling mechanism involves GPCR-mediated cation channel activation and a Gαi/o-coupled signaling pathway, which is being further investigated.