N-Methyl-N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)formamide
Basic information
- CAS
14686-61-4- Standard SMILES
COc1cc2c(c(OC)c1OC)-c1ccc(OC)c(=O)cc1[C@@H](N(C)C=O)CC2- InChIKey
HTWMEJLBEVTMMZ-INIZCTEOSA-N- Molecular formula
- C22H25NO6
- Average molar mass
- 399.4 g/mol
- Monoisotopic mass
- 399.16818752
Overview
N-Formyldemecolcine is a member of acetamides, an alkaloid and a carbotricyclic compound.
Names & identifiers
- Preferred name
- N-Methyl-N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)formamide
- IUPAC
- N-methyl-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamide
- English name
- N-Formyldemecolcine
- Molecular formula
- C22H25NO6
- Molecular weight
- 399.44
Names & synonyms
N-Formyldemecolcine14686-61-4COLCHICINE, N-DEACETYL-N-FORMYL-N-METHYL-DTXSID00163528N-methyl-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]formamideN-methyl-N-((7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo(a)heptalen-7-yl)formamideRefChem:1091917DTXCID9086019N-Methyl-N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)formamideN-FormyldemeocolcineNSC 315260BRN 3179104
Show more names
(S)-6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylformylamino)benzo[a]heptalene-9(5H)-one(S)-7-(N-Methyl-N-formylamino)-6,7-dihydro-1,2,3,10-tetramethoxybenzo[a]heptalen-9(5H)-oneFormamide, N-methyl-N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-
NSC315260Formamide, N-methyl-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-,CHEMBL315193SCHEMBL38656948CHEBI:80675NSC-315260NCI60_002713HY-164510
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 74.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 727
Physicochemical properties
- Melting point
- 187 · 187-8°C
- Boiling point
- 705.1 · 705.1±60.0 °C(Predicted)
- Density
- 1.25 · 1.25±0.1 g/cm3(Predicted)
- pka
- -0.91 · -0.91±0.40(Predicted)
Chemistry & industry
Applications
DescriptionThis alkaloid has been isolated from the seeds and corms of Colchicum autumnale, C. cornigerum, Gloriosa virescens and Littoria modesta. The melting point of that material obtained from C. cornigerum is the higher of the two values given above. The base has specific rotation of [αJ[α]D-189°C(CHCl) and [αJl - 2020 ± 50 (c 0.79, EtOH).
UsesN-Formyldemecolcine is a colchicine precursor that contains the characteristic tropolone ring and pharmacophore of colchicine. N-Formyldemecolcine can be synthesized de novo by genetically engineering transgenic Nicotiana benthamiana and atypical cytochrome P450s that catalyze the production of colchicine's unique carbon scaffold[1].
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: N-Formyldemecolcine is a member of acetamides, a carbotricyclic compound and an alkaloid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…