15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one

• ChemBase ID: 129152
• Molecular Formular: C20H19NO5
• Molecular Mass: 353.36856
• Monoisotopic Mass: 353.12632271
• SMILES: c12cc3OCOc3cc1CCN(C)Cc1c(CC2=O)ccc2c1OCO2
• Canonical SMILES: CN1CCc2cc3OCOc3cc2C(=O)Cc2c(C1)c1OCOc1cc2
• InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
• InChIKey: GPTFURBXHJWNHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^4,^1^2.0^6,^1^0.0^1^8,^2^2]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one; 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^4,^1^2.0^6,^1^0.0^1^8,^2^2]tetracosa-1(24),4,6(10),11,17,22-hexaen-3-one
• IUPAC Traditional name: protopine
• Synonyms: Protopine; 4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one; 7-Methyl-2,3:9,10-bis(methylenedioxy)-7,13a-secoberbin-13a-one; Biflorine; Corydinine; Fumarin; Fumarine; Macleyine; Protopin; Protopine

Database IDs

• CAS Number: 130-86-9
• PubChem SID: 162223449
• PubChem CID: 4970
• CHEMBL: 486179
• Wikipedia Title: Protopine

CALCULATED PROPERTIES

• Acid pKa: 15.816586
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.4857821
• LogD (pH = 7.4): 2.5914571
• Log P: 2.5929854
• Molar Refractivity: 94.5688 cm^3
• Polarizability: 36.68139 Å^3
• Polar Surface Area: 57.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1:15 in chloroform; Dioxane; DMSO; practically insoluble in water
• Apperance: Off-White Solid; Powder; white crystals
• Melting Point: 203-205°C; 208 °C
• Density: 1.399 g/cm^3

Safety Information

• Storage Condition: Refrigerator

Product Information

• Classification: Rare Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - P838870

Protopine is a Ca2+ channel blocker and antiplatelet agent. Immunomodulator.

REFERENCES

• Janbaz, K., et al.: Pharmacol. Res., 38, 215 (1998)
• Lai, C., et al.: Clin. Chem., 45, 229 (1998)
• Ma, H., et al.: J. Pharm. Biom. Anal., 49, 440 (1998)