Rugulovasine A
Basic information
- CAS
26909-33-1- Standard SMILES
CN[C@H]1Cc2c[nH]c3cccc(c23)[C@]12C=C(C)C(=O)O2- InChIKey
QTWQJTORJVFWAQ-XJKSGUPXSA-N- Molecular formula
- C16H16N2O2
- Average molar mass
- 268.31 g/mol
- Monoisotopic mass
- 268.12117776
Overview
Rugulovasine A is a member of indoles.
Names & identifiers
- Preferred name
- Rugulovasine A
- IUPAC
- (4S,5R)-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-furan]-2'-one
- English name
- rugulovasine A
- Molecular formula
- C16H16N2O2
- Molecular weight
- 268.31
Names & synonyms
Rugulovasine A26909-33-190DEE096C5DTXSID20949700(4S,5R)-3'-methyl-4-(methylamino)spiro(3,4-dihydro-1H-benzo(cd)indole-5,5'-furan)-2'-one(4S,5R)-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-furan]-2'-oneRefChem:180305DTXCID50152815328375-03-3RUGULOVASINE A [MI]UNII-90DEE096C5CHEBI:222539
Show more names
RUGULOVASINASpiro[benz[cd]indole-5(1H),2'(5'H)-furan]-5'-one, 3,4-dihydro-4'-methyl-4-(methylamino)-, (2'R,4S)-rel-
Q27271312(5R)-3'-methyl-(methylamino)spiro[[?]-5,5'-furan]-2'-one(4S,5R)-3'-methyl-4-(methylamino)spiro[3,4-dihydro-1H-benzo[cd]indole-5,5'-uran]-2'-one(2'R,4S)-4'-Methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-onePIRO(BENZ(CD)INDOLE-5(1H),2'(5'H)-FURAN)-5'-ONE, 3,4-DIHYDRO-4'-METHYL-4-(METHYLAMINO)-, (2'R,4S)-REL-Spiro(benz(cd)indole-5(1H),2'(5'H)-furan)-5'-one, 3,4-dihydro-4'-methyl-4-(methylamino)-, (2'R,4S)-rel-SPIRO(BENZ(CD)INDOLE-5(1H),2'(5'H)-FURAN)-5'-ONE, 3,4-DIHYDRO-4'-METHYL-4-(METHYLAMINO)-, CIS-Spiro(benz(cd)indole-5(1H),2'(5'H)-furan)-5'-one, 3,4-dihydro-4'-methyl-4-(methylamino)-, cis-(+-)-
Database identifiers
- CAS
26909-33-1- PubChem CID
- 115153
- DTXSID
DTXSID20949700- ChEBI
CHEBI:222539- UNII
- 90DEE096C5
- Nikkaji
- J237.984H
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 54.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 475
Physicochemical properties
- Melting point
- 138 ° · 138° (dec)
- alpha
- 22436 · 22436 -3.0° (pyridine)
- Boiling point
- 550.294 · 550.294±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.329 · 1.329±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 16.773 · 16.773±0.60(predicted)
- FDA UNII
- 90 DEE096C5 · 90DEE096C5
Chemistry & industry
Applications
DescriptionA non-crystallizable alkaloid, this base has been obtained from cultures of Penicillium concavorugulosum. It is slightly laevorotatory with [α]22436 - 3.0° (c 1.0, pyridine). The five-membered lactone ring is unsaturated and on catalytic hydrogenation the alkaloid forms the crystalline dihydro derivative, m.p. l49-l5l oC. One of the nitrogen atoms is present in the indole ring, the other being a methylamino group.
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