LINOLEAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H33NO
Molecular Weight	279.4607
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(N)=O

InChI

InChIKey=SFIHQZFZMWZOJV-HZJYTTRNSA-N

InChI=1S/C18H33NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H2,19,20)/b7-6-,10-9-

HIDE SMILES / InChI

Molecular Formula	C18H33NO
Molecular Weight	279.4607
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27595606 | https://www.ncbi.nlm.nih.gov/pubmed/11212875

Linoleamide, an endogenous sleep-inducing lipid, which inhibits sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), an enzyme, maintaining intracellular Ca2+ homeostasis by sequestering cytosolic Ca2+ into SR/ER stores. And thus, linoleamide modulates the intracellular Ca2+ homeostasis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 5 Target ID: P16615 Gene ID: 488.0 Gene Symbol: ATP2A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27595606	Inhibitor 8297		6.0 µM [Ki]
Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 2 Target ID: Q93084\|\|\|Q6JHX1 Gene ID: 489.0 Gene Symbol: ATP2A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27595606	Inhibitor 8297		6.8 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells.	2001 Jan 19	11212875
Inhibitory action of linoleamide and oleamide toward sarco/endoplasmic reticulum Ca(2+)-ATPase.	2017 Jan	27595606

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Three major sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) isoforms, rSERCA1a, hSERCA2b, and hSERCA3a, were individually overexpressed in COS-1 cells, and the inhibitory action of linoleamide (at a concentration ranging from 0 to 300 uM) on Ca2+-ATPase activity of SERCA was examined.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:58:51 GMT 2023` Edited by `admin` on `Fri Dec 15 18:58:51 GMT 2023`
Record UNII	5340S2UXSP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LINOLEAMIDE

Official Name

English

LINOLEIC ACID AMIDE

Systematic Name

English

LINOLEAMIDE (LINOLEIC ACID AMIDE)

Common Name

English

LINOLEAMIDE [INCI]

Common Name

English

9,12-OCTADECADIENAMIDE

Systematic Name

English

9,12-OCTADECADIENAMIDE, (9Z,12Z)-

Systematic Name

English

Code System Code Type Description

FDA UNII

5340S2UXSP