Basic information
- CAS
475-67-2- Standard SMILES
COc1ccc2c(c1O)-c1c(OC)c(OC)cc3c1[C@H](C2)N(C)CC3- InChIKey
QELDJEKNFOQJOY-ZDUSSCGKSA-N- Molecular formula
- C20H23NO4
- Average molar mass
- 341.4 g/mol
- Monoisotopic mass
- 341.16270821
Overview
Isocorydine is an aporphine alkaloid.
Names & identifiers
- Preferred name
- (+)-Isocorydine
- IUPAC
- (6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
- English name
- Isocorydine hydrochloride
- Molecular formula
- C20H23NO4
- Molecular weight
- 341.4
Names & synonyms
Isocorydine475-67-2(+)-IsocorydineArtabotrinLuteaninUzokoridind-IsocorydineL-(+)-IsocorydineS-(+)-IsocorydineLindcarpine, N,O-dimethyl-Aporphin-11-ol, 1,2,10-trimethoxy-(+)-(S)-Isocorydine
Show more names
LUTEANINEAids138466Aids-138466lsocorynoline
(S)-(+)-Isocorydine3B5E87JEOX4H-Dibenzo(de,g)quinolin-11-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-, (S)-DTXSID201023580NSC-32979(6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol6a-alpha-APORPHIN-11-OL, 1,2,10-TRIMETHOXY-NSC-645316
Database identifiers
- CAS
475-67-2- PubChem CID
- 10143
- DTXSID
DTXSID201023580- ChEMBL
CHEMBL489525- ChEBI
CHEBI:6000- UNII
- 3B5E87JEOX
- Nikkaji
- J5.971D
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 51.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 475
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical diffusion
Melting Point185 °C
Physical DescriptionSolid
Collision Cross Section181.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 216 · 216-220 °C(lit.)
- alpha
- 20 · D20 +195° (chloroform)
- Boiling point
- 477.03 °C · 477.03°C (rough estimate)
- Density
- 1.2064 · 1.2064 (rough estimate)
- refractive index
- 1.5614 · 1.5614 (estimate)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Cryst.
- pka
- 9.41 · 9.41±0.20(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Summary
Isocorydine induces G2/M phase arrest by increasing cyclin B1 and p-CDK1 expression levels, which was caused by decreasing the expression and inhibiting the activation of Cdc25C. The phosphorylation levels of Chk1 and Chk2 were increased after ICD treatment. Furthermore, G2/M arrest induced by ICD can be disrupted by Chk1 siRNA but not by Chk2 siRNA. In addition, isocorydine treatment led to a decrease in the percentage of CD133+ PLC/PRF/5 cells. Interestingly, isocorydine treatment dramatically decreased the tumorigenicity of SMMC-7721 and Huh7 cells. (A15211)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- 3
- rtecs
- CE1057950
- Toxicity
- LD50 intraperitoneal in mouse: 104mg/kg
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Uses(S)-Isocorydine is found in cherimoya.
Applications
DescriptionIsocorydine is an aporphine alkaloid that has been found in A. squamosa that has vasodilatory and anticancer activities. It reduces the action potential duration and increases the effective refractory period in isolated canine Purkinje fibers when used at a concentration of 30 μM. Isocorydine induces relaxation of norepinephrine-precontracted isolated rabbit aortic strips with an EC50 value of 12.6 μM. It is cytotoxic to A549 lung cancer cells (IC50 = 197.7 μM), as well as Huh7, HepG2, SNU-449, and SNU-387 hepatic cancer cells (IC50s = 161.3, 148, 262.2, and 254.1 μg/ml, respectively). Isocorydine, in combination with doxorubicin, reduces tumor growth in a Huh7 mouse xenograft model.
UsesIsocorydine is an alkaloid inhibitor of eukaryotic kinases.
UsesIsocorydine Hydrochloride is the hydrochloric acid of Isocorydine(I797000) which is an alkaloid inhibitor of eukaryotic kinases.
Usessedative, cholinergic
Upstream & downstream products
Downstream products
Suppliers100 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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