PALMITOYL GLYCINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H35NO3
Molecular Weight	313.4754
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC(=O)NCC(O)=O

InChI

InChIKey=KVTFEOAKFFQCCX-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C18H35NO3
Molecular Weight	313.4754
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18424551 | https://www.ulprospector.com/en/na/PersonalCare/Detail/1432/91748/TIMECODE

N-palmitoyl glycine, an endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. N-palmitoyl glycine is used in cosmetic under the brand name TIMECODE™ for deep wrinkles and helps relieve chronic silent inflammation, increases micro-circulation due to poor oxygenation and lack of nutrients. This product is also recommended for sensitive skin and for tired skin.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcium Influx 2 Target ID: Calcium Influx Sources: https://www.ncbi.nlm.nih.gov/pubmed/18424551	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Deep wrinkles 2 Sources: https://www.ulprospector.com/en/na/PersonalCare/Detail/1432/91748/TIMECODE	Palliative		Not Provided 504	TIMECODE Approved Use Unknown

PubMed

Title	Date	PubMed
Pivotal role of water in the mechanism of P450BM-3.	2001 Nov 13	11695892
HPLC analysis of fatty acyl-glycine in the aqueous methanesulfonic acid hydrolysates of N-terminally fatty acylated peptides.	2003 Aug	12913269
Effects of feeding Spodoptera littoralis on lima bean leaves. I. Membrane potentials, intracellular calcium variations, oral secretions, and regurgitate components.	2004 Apr	15051862
Observation of ligand binding to cytochrome P450 BM-3 by means of solid-state NMR spectroscopy.	2005 Oct 12	16201802
Structure-guided recombination creates an artificial family of cytochromes P450.	2006 May	16594730
Conformational equilibrium of cytochrome P450 BM-3 complexed with N-palmitoylglycine: a replica exchange molecular dynamics study.	2006 May 3	16637647
Interactions of substrates at the surface of P450s can greatly enhance substrate potency.	2007 Dec 11	18004886
Conformational dynamics of substrate in the active site of cytochrome P450 BM-3/NPG complex: insights from NMR order parameters.	2007 Jan 24	17226994
Conformational dynamics of the cytochrome P450 BM3/N-palmitoylglycine complex: the proposed "proximal-distal" transition probed by temperature-jump spectroscopy.	2007 Jul 12	17571881
Laser photoexcitation of NAD(P)H induces reduction of P450 BM3 heme domain on the microsecond time scale.	2007 May 23	17465554
Natural variation of potato allene oxide synthase 2 causes differential levels of jasmonates and pathogen resistance in Arabidopsis.	2008 Jul	18431595
N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons.	2008 Jul	18424551
A single mutation in P450BM-3 enhances acyl homoserine lactone: acyl homoserine substrate binding selectivity nearly 250-fold.	2008 Jul 31	18586345
Novel endogenous N-acyl glycines identification and characterization.	2009	19647113
Orphan endogenous lipids and orphan GPCRs: a good match.	2009 Sep	19379823
Two new lipoaminoacids with complementary modes of action: new prospects to fight out against skin aging.	2010 Feb	19732187
N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor.	2010 Mar 26	20346144

Sample Use Guides

In Vivo Use Guide

solution for skin firmness

Route of Administration: Topical

In Vitro Use Guide

To investigate the effect of N-palmitoyl glycine (PalGly) on primary sensory neurons, calcium influx was recorded in the DRG-like F-11 cells (rat dorsal root ganglion neuron × mouse neuroblastoma). PalGly (10 μM) induced a transient influx of calcium in F-11 cells. The effect was immediate, and the initial increase was followed by a gradual return to baseline after 5 min of PalGly addition, with an EC50 = 5.5 μM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:19:34 GMT 2023` Edited by `admin` on `Fri Dec 15 20:19:34 GMT 2023`
Record UNII	M6V3RIU5KI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PALMITOYL GLYCINE

Official Name

English

GLYCINE, N-(1-OXOHEXADECYL)-

Systematic Name

English

TIMECODE

Brand Name

English

PALMITOYL GLYCINE [INCI]

Common Name

English

PALMITOILGLICINA

Brand Name

English

Code System Code Type Description

DAILYMED

M6V3RIU5KI