1859-87-6

Basic information

• Product Name: ECHINULIN
• Synonyms: ECHINULIN;echinuline;(3S,6S)-3-[[2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione;2-(1,1-Dimethyl-2-propenyl)-5,7-diisopentenylcyclo(L-Trp-L-Ala-);(3S,6S)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methyl-piperazine-2,5-quinone;(3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
• CAS NO: 1859-87-6
• Molecular Formula: C29H39N3O2
• Molecular Weight: 461.64
• Mol File: 1859-87-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 242-243°
• Boiling Point: 695.3°Cat760mmHg
• Flash Point: 374.3°C
• Appearance: /
• Density: 1.068g/cm³
• Vapor Pressure: 3.51E-19mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: ECHINULIN(CAS DataBase Reference)
• NIST Chemistry Reference: ECHINULIN(1859-87-6)
• EPA Substance Registry System: ECHINULIN(1859-87-6)

Safety Data

• Hazardous Substances Data: 1859-87-6(Hazardous Substances Data)

Usage

Description

Echinulin, a diketopiperazine metabolite, is derived from fungi and has been observed to cause liver and lung damage in rabbits when administered at a dose of 10 mg/kg. It does not exhibit activity at the δ, κ, or μ-opioid receptors or the cannabinoid CB1 and CB2 receptors.

Uses

Since the provided materials do not specify any particular applications for Echinulin, it is not possible to list its uses based on the given information. However, if there were any applications, the format for listing them would be as follows:
Used in [Application Industry]:
ECHINULIN is used as [application type] for [application reason]
For example, if Echinulin had a specific application in the pharmaceutical industry, it would be listed as:
Used in Pharmaceutical Industry:
ECHINULIN is used as a [specific application type, e.g., therapeutic agent] for [application reason, e.g., treating a particular condition or disease].

InChI:InChI=1/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-15,19,24,32H,1,12-13,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1

Upstream product

• 21008-43-5 (3S,6S)-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl-6-methyl-2,5-piperazinedione 
• 17079-37-7 (3S,6S)-3-(3'-indolylmethyl)-6-methylpiperazine-2,5-dione 

Relevant articles and documents

Two Prenyltransferases Govern a Consecutive Prenylation Cascade in the Biosynthesis of Echinulin and Neoechinulin

Two prenyltransferases from Aspergillus ruber control the echinulin biosynthesis via exceptional sequential prenylations. EchPT1 catalyzes the first prenylation step, leading to preechinulin. The unique EchPT2 attaches, in a consecutive prenylation cascade, up to three dimethylallyl moieties to preechinulin and its dehydro forms neoechinulins A and B, resulting in the formation of at least 23 2- to 4-fold prenylated derivatives. Confirming these products in fungal extracts unravels the unprecedented catalytic relevance of EchPT2 for structural diversity.