Basic information
- CAS
131-07-7- Standard SMILES
COC(=O)C1=CO[C@@H](C)[C@H]2Cn3ccc4c5ccccc5nc-4c3C[C@H]12- InChIKey
WYTGDNHDOZPMIW-VBNZEHGJSA-N- Molecular formula
- C21H20N2O3
- Average molar mass
- 348.4 g/mol
- Monoisotopic mass
- 348.1473925
Overview
Serpentine is an indole alkaloid that is 18-oxayohimban dehydrogenated at positions 3, 4, 5, 6, 16 and 17 and substituted by a methyl group at the 19alpha position and by a methoxycarbonyl group at position 16. It is a zwitterion, a carboxylic ester, an iminium betaine, a member of quinolizines and an indole alkaloid. It is a conjugate base of a serpentine(1+). It derives from a hydride of a 18-oxayohimban.
Names & identifiers
- Preferred name
- Serpentine
- IUPAC
- methyl (15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylate
- English name
- Serpentine
- Molecular formula
- C21H20N2O3
- Molecular weight
- 348.4
Names & synonyms
Serpentine (alkaloid)3,4,5,6-TetradehydroajmalicineB503RKE34FCHEBI:9119methyl (19alpha)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide-16-carboxylatemethyl (15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylateNSC-407301(19 alpha)-3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbanium3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19a-methyl-20a-oxayohimbaniumOxayohimbanium, 3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyl-, (19alpha)-SchweizeriteOnion jade
Show more names
methyl (15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylateRefChem:931639242-570-5hydron;methyl (15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-1,3,5,7,9,11,18-heptaene-19-carboxylateSerpentine131-07-7Serpentine hydroxide, inner salt(19alpha)-3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbanium
Database identifiers
- CAS
131-07-7、18786-24-8- PubChem CID
- 73073
- DTXSID
DTXSID80927029- ChEBI
CHEBI:9119- UNII
- B503RKE34F
- Nikkaji
- J247.674F
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 53.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 606
Physicochemical properties
- Boiling point
- 490.09 °C · 490.09°C (rough estimate)
- Density
- 1.1379 · 1.1379 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
Chemistry & industry
Additional notes
DefinitionChEBI: Serpentine is an indole alkaloid that is 18-oxayohimban dehydrogenated at positions 3, 4, 5, 6, 16 and 17 and substituted by a methyl group at the 19alpha position and by a methoxycarbonyl group at position 16. It is an indole alkaloid, a member of quinolizines, a carboxylic ester, an iminium betaine and a zwitterion. It is a conjugate base of a serpentine(1+). It derives from a hydride of a 18-oxayohimban.
Related reactions
0 records
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Compound notes
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