Echinulin
Basic information
- CAS
1859-87-6- Standard SMILES
C=CC(C)(C)c1[nH]c2c(CC=C(C)C)cc(CC=C(C)C)cc2c1C[C@@H]1NC(=O)[C@H](C)NC1=O- InChIKey
DIKMWTRJIZQJMY-CYFREDJKSA-N- Molecular formula
- C29H39N3O2
- Average molar mass
- 461.6 g/mol
- Monoisotopic mass
- 461.3042275
Overview
Echinulin is an indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species. It has a role as a marine metabolite, a plant metabolite and an Aspergillus metabolite. It is a member of indoles, an indole alkaloid, a member of 2,5-diketopiperazines and an olefinic compound.
Names & identifiers
- Preferred name
- Echinulin
- IUPAC
- (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
- English name
- ECHINULIN
- Molecular formula
- C29H39N3O2
- Molecular weight
- 461.64
Names & synonyms
echinulin(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(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-dioneRefChem:1084040Echinuline1859-87-6(3s,6s)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}piperazine-2,5-dione3DP19VPN8UCHEMBL251450UNII-3DP19VPN8UD-Gluconic acid, 2-(acetylamino)-2-deoxy-, delta-lactone(3S,6S)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methyl-piperazine-2,5-dione
Show more names
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-[[2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione2,5-Piperazinedione,3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-6-methyl-,(3S,6S)-
Properties
Computed structural properties
- XLogP
- 7
- Topological polar surface area
- 74 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 8
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 834
Physicochemical properties
- Melting point
- 242 · 242-243°
- alpha
- 20 · D20 -26.0° (chloroform)
- Boiling point
- 695.3 · 695.3±55.0 °C(Predicted)
- Density
- 1.068 · 1.068±0.06 g/cm3(Predicted)
- solubility
- Methanol: soluble
- form
- A solid
- pka
- 13.05 · 13.05±0.60(Predicted)
- color
- White to off-white
- FDA UNII
- 3 DP19VPN8U · 3DP19VPN8U
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionEchinulin 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.
UsesEchinulin is a metabolite of diketopiperazine.
Additional notes
DefinitionChEBI: Echinulin is an indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species. It has a role as an Aspergillus metabolite, a marine metabolite and a plant metabolite. It is a member of indoles, a member of 2,5-diketopiperazines, an olefinic compound and an indole alkaloid.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…