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P0064

PalGly

Name: PalGly
Brand: SIGMA

≥98% (HPLC), solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):

C₁₈H₃₅NO₃

Número de CAS:

2441-41-0

Peso molecular:

313.48

MDL number:

MFCD00153471

UNSPSC Code:

12352200

PubChem Substance ID:

329820003

NACRES:

NA.77

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Sigma-Aldrich

O0383

N-Oleoylethanolamine

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)

Certificados de análisis (COA)

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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)

Conformational equilibrium of cytochrome P450 BM-3 complexed with N-palmitoylglycine: a replica exchange molecular dynamics study.

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

Orphan endogenous lipids and orphan GPCRs: a good match.

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

Pivotal role of water in the mechanism of P450BM-3.

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

Opportunistic activation of TRP receptors by endogenous lipids: exploiting lipidomics to understand TRP receptor cellular communication.

Heather B Bradshaw et al.

Life sciences, 92(8-9), 404-409 (2012-11-28)

Transient receptor potential channels (TRPs) form a large family of ubiquitous non-selective cation channels that function as cellular sensors and in many cases regulate intracellular calcium. Identification of the endogenous ligands that activate these TRP receptors is still under intense

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