8-Chlororugulovasine A
Basic information
- CAS
59787-45-0- Standard SMILES
CN[C@H]1Cc2c[nH]c3c(Cl)ccc(c23)[C@]12C=C(C)C(=O)O2- InChIKey
SDYOUVJWVNBXPX-BLLLJJGKSA-N- Molecular formula
- C16H15ClN2O2
- Average molar mass
- 302.75 g/mol
- Monoisotopic mass
- 302.0822054
Overview
8-chlororugulovasine A is a member of indoles.
Names & identifiers
- Preferred name
- 8-Chlororugulovasine A
- IUPAC
- (4S,5R)-8-chloro-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-furan]-2'-one
- English name
- 8-chlororugulovasine A
- Molecular formula
- C16H15ClN2O2
- Molecular weight
- 302.76
Names & synonyms
8-Chlororugulovasine AToxin B (Penicillium islandicum)59787-45-0L5FM3F581NDTXSID50208519(4S,5R)-8-chloro-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-furan]-2'-one(4S,5R)-8-chloro-3'-methyl-4-(methylamino)spiro(3,4-dihydro-1H-benzo(cd)indole-5,5'-furan)-2'-oneRefChem:107029DTXCID50131010UNII-L5FM3F581NCHEBI:222552Spiro(benz(cd)indole-5(1H),2'(5'H)-furan)-5'-one, 3,4-dihydro-8-chloro-4'-methyl-4-(methylamino)-, cis-(+-)-
Show more names
Spiro[benz[cd]indole-5(1H),2'(5'H)-furan]-5'-one, 8-chloro-3,4-dihydro-4'-methyl-4-(methylamino)-, (2'R,4S)-rel-
(2'R,4S)-8-Chloro-4'-methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-one(4S,5R)-8-chloro-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-uran]-2'-oneREL-(2'R,4S)-8-CHLORO-3,4-DIHYDRO-4'-METHYL-4-(METHYLAMINO)SPIRO(BENZ(CD)INDOLE-5(1H),2'(5'H)-FURAN)-5'-ONESPIRO(BENZ(CD)INDOLE-5(1H),2'(5'H)-FURAN)-5'-ONE, 8-CHLORO-3,4-DIHYDRO-4'-METHYL-4-(METHYLAMINO)-, (2'R,4S)-REL-SPIRO(BENZ(CD)INDOLE-5(1H),2'(5'H)-FURAN)-5'-ONE, 8-CHLORO-3,4-DIHYDRO-4'-METHYL-4-(METHYLAMINO)-, CIS-(+/-)-
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 54.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 509
Physicochemical properties
- Melting point
- Ci o . NHMe
- Boiling point
- 567.985 · 567.985±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.423 · 1.423±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 15.192 · 15.192±0.60(predicted)
- FDA UNII
- 5 FM3F581N · L5FM3F581N
Chemistry & industry
Applications
DescriptionWhen Penicillium islandicum is grown on freshly dug green peanuts it elaborates two chlorine-containing alkaloids which are the first naturally occurring chlorinated ergot bases discovered. The bases have been separated by chromatography on silica gel and are stereoisomeric, being readily interconverted by refluxing in methanol. This alkaloid forms an amorphous white powder and has the structure shown above which is based upon spectroscopic data.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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