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P0064

Sigma-Aldrich

PalGly

≥98% (HPLC), solid

Synonyma:

N-(1-Oxohexadecyl)glycine, N-Hexadecanoylglycine, Hexadecanoylaminoacetic acid, N-palmitoyl glycine

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About This Item

Empirický vzorec (Hillův zápis):
C18H35NO3
Číslo CAS:
2441-41-0
Molekulová hmotnost:
313.48
MDL number:
MFCD00153471
UNSPSC Code:
12352200
PubChem Substance ID:
329820003
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

O=C(CCCCCCCCCCCCCCC)NCC(O)=O

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)

InChI key

KVTFEOAKFFQCCX-UHFFFAOYSA-N

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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.

Features and Benefits

This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Osvědčení o analýze (COA)

Lot/Batch Number
098K4604V
098K46041
098K4604

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Heather B Bradshaw et al.
Prostaglandins & other lipid mediators, 89(3-4), 131-134 (2009-04-22)
A large and growing family of over 70 endogenous lipids of the basic structure N-acyl amide has been identified during the last 10 years. Only a few of these lipids have been characterized for biological activity, however, those that have
D C Haines et al.
Biochemistry, 40(45), 13456-13465 (2001-11-07)
Cytochrome P450s constitute a superfamily of enzymes that catalyze the oxidation of a vast number of structurally and chemically diverse hydrophobic substrates. Herein, we describe the crystal structure of a complex between the bacterial P450BM-3 and the novel substrate N-palmitoylglycine
Krishna Pratap Ravindranathan et al.
Journal of the American Chemical Society, 128(17), 5786-5791 (2006-04-28)
UV-vis absorbance measurements and associated studies of cytochrome P450 BM-3 in complex with N-palmitoylglycine (NPG) indicate that a conformational change occurs in the active site of the complex where the terminal atoms of the ligand move from a site distant
Conformational dynamics of substrate in the active site of cytochrome P450 BM-3/NPG complex: insights from NMR order parameters.
Krishna Pratap Ravindranathan et al.
Journal of the American Chemical Society, 129(3), 474-475 (2007-01-18)
Kristen A Jeffries et al.
Journal of lipid research, 57(5), 781-790 (2016-03-27)
Long-chain fatty acid amides are signaling lipids found in mammals and other organisms; however, details of the metabolic pathways for the N-acylglycines and primary fatty acid amides (PFAMs) have remained elusive. Heavy-labeled precursor and subtraction lipidomic experiments in mouse neuroblastoma
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