Docosahexaenoyl Ethanolamide - ≥98%, 25mg/ml in ethanol , CAS No.162758-94-3

CAS: 162758-94-3 Cat. No.: D335344 Molecular Weight: 371.56

GRADE & PURITY ≥98%, 25mg/ml in ethanol

Synonyms

HMS3650G19 | Q27158436 | N-(2-hydroxyethyl)-4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenamide | SCHEMBL1228084 | Synaptamide | Anandamide (22:6, n-3) | BDBM50463963 | N-(2-Hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide | EX-A7999E | (4Z,7Z,10Z,13Z,16Z,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Docosahexaenoyl Ethanolamide (DHEA) is an ethanolamine amide of DHA that has been detected in both retina and brain at concentrations similar to those for arachidonoyl ethanolamide (AEA). Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, particularly in the retina and brain. A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets on a DHA-supplemented diet compared to a DHA-free control diet. DHEA binds rat brain CB1 receptor with a K|i|of 324 nM, which is about 10-fold higher than the K|i|for AEA. DHEA inhibits shaker-related voltage-gated potassium channels in the brain slightly better than AEA, with an IC|50|of 1.5 μM.

Specifications

Synonyms

HMS3650G19 | Q27158436 | N-(2-hydroxyethyl)-4(Z), 7(Z), 10(Z), 13(Z), 16(Z), 19(Z)-docosahexaenamide | SCHEMBL1228084 | Synaptamide | Anandamide (22:6, n-3) | BDBM50463963 | N-(2-Hydroxyethyl)docosa-4, 7, 10, 13, 16, 19-hexaenamide | EX-A7999E | (4Z, 7Z, 10Z, 13Z, 16Z,

Specifications & Purity

≥98%, 25mg/ml in ethanol

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.

Action Type

AGONIST

Purity

≥98%

Product Properties

• pKa: pKa: 15.45 (Predicted), pKa: -0.48 (Predicted)
• Ki Data: CB1: Ki= 324 nM (rat brain)

Names and Identifiers

• Canonical Smiles: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)NCCO
• IUPAC Name: (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide
• InChIKey: GEEHOLRSGZPBSM-KUBAVDMBSA-N
• INCHI: 1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO
• WGK Germany: 3
• Molecular Weight: 371.56
• Reaxy-Rn: 27889054
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27889054&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,2-aminoalcohols
            • Level7 N-acylethanolamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines - 1,2-aminoalcohols
• Direct Parent: N-acylethanolamines
• Alternative Parents: N-acyl amines Secondary carboxylic acid amides Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acylethanolamine - Fatty amide - N-acyl-amine - Fatty acyl - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Alcohol - Organooxygen compound - Primary alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acylethanolamines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
• External Descriptors: N-acyl ethanolamines (endocannabinoids)

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)

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

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

143B (353 Activities)

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MG-63 (795 Activities)

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A549 (127892 Activities)

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Associated Targets(non-human)

Faah Anandamide amidohydrolase (3907 Activities)

Discover Target: Faah

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Trpv2 Transient receptor potential cation channel subfamily V member 2 (148 Activities)

Discover Target: Trpv2

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Mus musculus (284745 Activities)

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RBL-2H3 (1162 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol, DMSO (~20 mg/ml), DMF (~20 mg/ml), PBS (pH 7.2) (~0.15 mg/ml), and water (0.15 mg/ml at 25° C).
• Refractive Index: n20D1.52 (Predicted)
• Boil Point(°C): 78° C
• Molecular Weight: 371.600 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 371.282 Da
• Monoisotopic Mass: 371.282 Da
• Topological Polar Surface Area: 49.300 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 510.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 6
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 6
• Covalently-Bonded Unit Count: 1