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P0064

Sigma-Aldrich

PalGly

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H35NO3
CAS Number:
2441-41-0
Molecular Weight:
313.48
MDL number:
MFCD00153471
UNSPSC Code:
12352200
PubChem Substance ID:
329820003
NACRES:
NA.77

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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)
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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