Linoleoyl glycine - ≥97% , CAS No.2764-03-6

CAS: 2764-03-6 Cat. No.: L333042 Molecular Weight: 337.5

GRADE & PURITY ≥97%

Synonyms

2-[[(9Z,12Z)-octadeca-9,12-dienoyl]amino]acetic acid | Glycine-linoleamide | SCHEMBL6681636 | NCGC00161201-06 | HMS1791I08 | IDI1_033916 | NCGC00161201-05 | J-016835 | linolyl glycine | HMS1361I08 | BRD-K76293260-001-02-6 | ((9Z,12Z)-Octadeca-9,12-dienoyl

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Linoleoyl glycine is an endogenous homolog of linoleoyl ethanolamide, an arachidonyl glycine. Arachidonyl glycine, the conjugate of arachidonic acid and glycine produced in mammalian skin, spinal cord and brain, is a structural counterpart of anandamide (AEA) that is reported to have analgesic activities in whole animal experiments. It has poor affinity for the central cannabinoid (CB1) receptor, high-affinity for the G protein-coupled receptor GPR-18, and is metabolically regulated by fatty acid amide hydrolase (FAAH) activity. Linoleoyl glycine inhibits the hydrolysis of AEA in FAAH-containing N18TG2 cell membranes (IC|50|~ 25 μM), which is less potent than that of arachidonyl glycine (IC|50|= 7 μM). The biological significance of linoleoyl glycine has not yet been determined.

Specifications

Synonyms

2-[[(9Z, 12Z)-octadeca-9, 12-dienoyl]amino]acetic acid | Glycine-linoleamide | SCHEMBL6681636 | NCGC00161201-06 | HMS1791I08 | IDI1_033916 | NCGC00161201-05 | J-016835 | linolyl glycine | HMS1361I08 | BRD-K76293260-001-02-6 | ((9Z, 12Z)-Octadeca-9, 12-dienoyl

Specifications & Purity

≥97%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504764150
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764150
• Canonical Smiles: CCCCCC=CCC=CCCCCCCCC(=O)NCC(=O)O
• IUPAC Name: 2-[[(9Z,12Z)-octadeca-9,12-dienoyl]amino]acetic acid
• InChIKey: YCRHZEHWEYAHCO-HZJYTTRNSA-N
• INCHI: 1S/C20H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h6-7,9-10H,2-5,8,11-18H2,1H3,(H,21,22)(H,23,24)/b7-6-,10-9-
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCC(=O)O
• Molecular Weight: 337.5
• Reaxy-Rn: 38603316
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38603316&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives
              • Level8 N-acyl-alpha amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - N-acyl-alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids
• Alternative Parents: N-acyl amines Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acyl-alpha-amino acid - Fatty amide - N-acyl-amine - Fatty acyl - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid - Monocarboxylic acid or derivatives - Carbonyl group - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HaCaT (4069 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)

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RAW264.7 (28094 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO, dimethyl formamide and ethanol.
• Molecular Weight: 337.500 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 337.262 Da
• Monoisotopic Mass: 337.262 Da
• Topological Polar Surface Area: 66.400 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 375.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1