Echinulin

Base Information

• Chemical Name: Echinulin
• CAS No.: 1859-87-6
• Molecular Formula: C₂₉H₃₉N₃O₂
• Molecular Weight: 461.648
• UNII: 3DP19VPN8U
• Nikkaji Number: J20.673C
• Wikidata: Q27257084
• Metabolomics Workbench ID: 129503
• ChEMBL ID: CHEMBL251450
• Mol file: 1859-87-6.mol

Synonyms:echinuline

Chemical Property of Echinulin

Chemical Property:

• Vapor Pressure: 3.51E-19mmHg at 25°C
• Melting Point: 242-243°
• Boiling Point: 695.3°Cat760mmHg
• Flash Point: 374.3°C
• PSA: 73.99000
• Density: 1.068g/cm³
• LogP: 5.85210
• XLogP3: 7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 461.30422750
• Heavy Atom Count: 34
• Complexity: 834

Purity/Quality:

98%,99%, ^*data from raw suppliers

Echinulin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)N1)CC2=C(NC3=C(C=C(C=C23)CC=C(C)C)CC=C(C)C)C(C)(C)C=C
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N1)CC2=C(NC3=C(C=C(C=C23)CC=C(C)C)CC=C(C)C)C(C)(C)C=C
• Description: Echinulin is a diketopiperazine metabolite found in fungi that, when administered to rabbits, at a dose of 10 mg/kg, leads to liver and lung damage. It has no activity at the δ, κ, or μ-opioid receptors or the cannabinoid CB1 and CB2 receptors.
• Uses: Echinulin is a metabolite of diketopiperazine.

Technology Process of Echinulin

There total 6 articles about Echinulin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(3S,6S)-3-(3'-indolylmethyl)-6-methylpiperazine-2,5-dione (17079-37-7,19943-35-2,22216-02-0,22216-03-1,22839-21-0,22839-22-1,22839-23-2,26384-48-5) → variecolorin L + C34H47N3O2 + cyclo-L-2-tert-dimethylallyl-4,5,7-tri-dimethylallyl-Trp-L-Ala + Echinulin (1859-87-6,19943-37-4,26384-49-6,35849-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: calcium chloride / 0.02 h / 37 °C / pH 7.5

2: calcium chloride / 0.05 h / 37 °C / pH 7.5

With calcium chloride;

DOI:10.1021/acs.orglett.7b02926

Reference yield:

(3S,6S)-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl-6-methyl-2,5-piperazinedione (21008-43-5) → variecolorin L + C34H47N3O2 + cyclo-L-2-tert-dimethylallyl-4,5,7-tri-dimethylallyl-Trp-L-Ala + Echinulin (1859-87-6,19943-37-4,26384-49-6,35849-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: calcium chloride / 0.05 h / 37 °C / pH 7.5

2: protein-EYE₉₈₇₄₆(EchPT₂)

With calcium chloride;

DOI:10.1021/acs.orglett.7b02926

Reference yield:

cyclo-L-alanyl-5-isopentenyl-2-(1',1'-dimethylallyl)-L-tryptophan → variecolorin L + C34H47N3O2 + cyclo-L-2-tert-dimethylallyl-4,5,7-tri-dimethylallyl-Trp-L-Ala + Echinulin (1859-87-6,19943-37-4,26384-49-6,35849-87-7)

Guidance literature:

With protein-EYE₉₈₇₄₆(EchPT₂);

DOI:10.1021/acs.orglett.7b02926

upstream raw materials:

(3S,6S)-3-(3'-indolylmethyl)-6-methylpiperazine-2,5-dione

(3S,6S)-3-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl-6-methyl-2,5-piperazinedione

Refernces