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Home > Encyclopedia > (5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide

(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide

(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide structure

(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide 

structure
  • CAS No:

    187947-37-1

  • Formula:

    C30H42N2O2

  • Chemical Name:

    (5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide

  • Synonyms:

    5,8,11,14-Eicosatetraenamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-,(5Z,8Z,11Z,14Z)-;5,8,11,14-Eicosatetraenamide,N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-,(all-Z)-;(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide;N-Arachidonoylserotonin;AA-5-HT

  • Categories:

    Biochemical Engineering  >  Inflammation Mediators

Description

N-arachidonoylserotonin is an N-acylserotonin obtained by formal condensation of the carboxy group of arachidonic acid with the primary amino group of serotonin. It has a role as a human metabolite, a signalling molecule, an antioxidant, an anti-inflammatory agent, an anticonvulsant, a capsaicin receptor antagonist and an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor. It is a member of phenols and a N-acylserotonin. It derives from an arachidonic acid.

(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide Basic Attributes

462.67

462.67

Characteristics

65.1

8.06880

yellow

DMSO: >10mg/mL

−20°C

Safety Information

3

Drug Information

AA-5-HT

(5Z,8Z,11Z,14Z)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-5,8,11,14-eicosatetraenamide Use and Manufacturing

Uses

Dual fatty acid amide hydrolase (FAAH) inhibitor/TRPV1 antagonist (IC 50 values are 5.6 μ M and 37-40 nM for FAAH and TRPV1 respectively). Inactive at cPLA 2 , CB 1 or 5-HT receptors. Displays strong analgesic activity against both acute and chronic peripheral pain.

Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802]

Computed Properties

Molecular Weight:462.7
XLogP3:7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:17
Exact Mass:462.324628587
Monoisotopic Mass:462.324628587
Topological Polar Surface Area:65.1
Heavy Atom Count:34
Complexity:652
Defined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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