(+)-Serpentine
Basic information
- CAS
18786-24-8- Standard SMILES
COC(=O)C1=CO[C@@H](C)[C@H]2C[n+]3ccc4c([nH]c5ccccc54)c3C[C@H]12- InChIKey
WYTGDNHDOZPMIW-VBNZEHGJSA-O- Molecular formula
- C21H21N2O3+
- Average molar mass
- 349.4 g/mol
- Monoisotopic mass
- 349.15521754
Overview
Serpentine(1+) is an organic cation that is the conjugate acid of serpentine. It is the major species at pH 7.3. It is a conjugate acid of a serpentine.
Names & identifiers
- Preferred name
- (+)-Serpentine
- IUPAC
- methyl (15R,16S,20S)-16-methyl-17-oxa-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8,11,18-heptaene-19-carboxylate
- English name
- Serpentine hydrogen tartrate
- Molecular formula
- C25H26N2O9
- Molecular weight
- 498.48
Names & synonyms
18786-24-8(+)-SerpentineDTXSID40940259RefChem:1048999DTXCID401765996CHEMBL355948855322-91-3serpentine(1+)orb1681706SCHEMBL26479502CHEBI:142531WYTGDNHDOZPMIW-VBNZEHGJSA-O
Show more names
Nsc 407301Einecs 242-570-5serpentine (alkaloid)Serpentine hydrochlorideSerpentine hydrogen tartrate3,4,5,6-Tetradehydroajmalicine(19α)-3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyl-oxayohimbanium(19 alpha)-3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbanium3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19α-methyl-18-oxayohimban-4-ium-1-ideOxayohimbanium, 3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyl-, (19alpha)- (9ci)
BDBM50608890TN4997AKOS032962081AE-508/2113102116-(Methoxycarbonyl)-19alpha-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 55.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 1
- Complexity
- 606
Physicochemical properties
- Melting point
- 158 ° · 158° (air-dried); mp 175° (after drying at 120° in a high vacuum, but still not entirely solvent-free)
- alpha
- 25 · D25 +292° (c = 0.27 in methanol); D25 +267° (c = 0.21 in ethanol)
- Boiling point
- 482.77 °C · 482.77°C (rough estimate)
- Density
- 1.2214 · 1.2214 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- color
- Yellow
- FDA UNII
- 503 RKE34F · B503RKE34F
Chemistry & industry
Additional notes
DefinitionChEBI: 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.
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