Corynoline
Basic information
- CAS
18797-79-0- Standard SMILES
CN1Cc2c(ccc3c2OCO3)[C@@]2(C)[C@@H](O)Cc3cc4c(cc3[C@@H]12)OCO4- InChIKey
IQUGPRHKZNCHGC-TYPHKJRUSA-N- Molecular formula
- C21H21NO5
- Average molar mass
- 367.4 g/mol
- Monoisotopic mass
- 367.14197277
Overview
Corynoline is a benzophenanthridine alkaloid that is chelidonine substituted by a methyl group at position 13. Isolated from the aerial parts of Corydalis incisa, it acts as an acetylcholinesterase inhibitor and also exhibits antineoplastic and hepatoprotective activity. It has a role as a metabolite, an antineoplastic agent, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a hepatoprotective agent. It is a member of isoquinolines, a secondary alcohol, a benzophenanthridine alkaloid, an organic heterohexacyclic compound and a cyclic acetal. It is functionally related to a chelidonine.
Names & identifiers
- Preferred name
- Corynoline
- IUPAC
- (1R,12S,13R)-13,24-dimethyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
- English name
- CORYNOLINE
- Molecular formula
- C21H21NO5
- Molecular weight
- 367.4
Names & synonyms
Corynoline13-methylchelidonineChelidonine, 13-methyl-ZQ9W3JU6N3DTXSID20940272(1R,12S,13R)-13,24-dimethyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-olCHEBI:65660(1R,12S,13R)-13,24-dimethyl-5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-olRefChem:128172DTXCID70136874318797-79-0(+)-corynoline
Show more names
CORYNOLINE(P)Corynoline-RM8-Dihydrokawain8-DihydrokavainCorynoline (Standard)dimethyl-, (5bR,6S,12bR)-Corynoline, 10 mM in DMSO13-Methylchelidonan-11β-ol
(11S,13R,14R)-corynoline(5BR,6S,12BR)-5B,13-DIMETHYL-5B,6,7,12B,13,14-HEXAHYDRO-[1,3]DIOXOLO[4',5':4,5]BENZO[1,2-C][1,3]DIOXOLO[4,5-I]PHENANTHRIDIN-6-OL[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-5b,13-dimethyl-, (5bR,6S,12bR)-68035-45-0UNII-ZQ9W3JU6N3CHEMBL4126384HY-N0826(invertedexclamationmarkA)-Corynoline
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 60.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 603
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 180 · 180~181℃
- Boiling point
- 504.2 · 504.2±50.0 °C(Predicted)
- Density
- 1.395 · 1.395±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
- pka
- 14.14 · 14.14±0.40(Predicted)
- form
- Solid
- color
- Off-White to Pale Yellow
- Stability
- Light Sensitive
- InChI
- InChI=1S/C21H21NO5/c1-21-14-3-4-15-19(27-10-24-15)13(14)8-22(2)20(21)12-7-17-16(25-9-26-17)5-11(12)6-18(21)23/h3-5,7,18,20,23H,6,8-10H2,1-2H3/t18-,20+,21-/m0/s1
- InChIKey
- IQUGPRHKZNCHGC-TYPHKJRUSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302+H312+H332 (95%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (95%)
Safety data
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H302+H312+H332
Chemistry & industry
Applications
DescriptionThe empirical formula of corynoline should read C21H21NO5
UsesCorynoline is an isoquinoline alkaloid with reported pharmacological activity such as cell adhesion inhibition, sedation and liver protection.
Additional notes
DefinitionChEBI: A benzophenanthridine alkaloid that is chelidonine substituted by a methyl group at position 13. Isolated from the aerial parts of Corydalis incisa, it acts as an acetylcholinesterase inhibitor and also exhibits antineoplastic and hepatoprotec ive activity.
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