6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^{4,9}.0^{15,19}]henicosa-1(21),4(9),5,7,14,19-hexaen-3-one

• ChemBase ID: 106716
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 369.15762284
• SMILES: COc1cc2c(cc1OC)C(=O)Cc1ccc3OCOc3c1CN(C)CC2
• Canonical SMILES: COc1cc2C(=O)Cc3ccc4c(c3CN(CCc2cc1OC)C)OCO4
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19(24-2)20(25-3)10-15(14)17(23)8-13-4-5-18-21(16(13)11-22)27-12-26-18/h4-5,9-10H,6-8,11-12H2,1-3H3
• InChIKey: XPOJSWHIKCNLEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^{4,9}.0^{15,19}]henicosa-1(21),4(9),5,7,14,19-hexaen-3-one; 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^4,^9.0^1^5,^1^9]henicosa-1(21),4,6,8,14,19-hexaen-3-one
• IUPAC Traditional name: 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^{4,9}.0^{15,19}]henicosa-1(21),4(9),5,7,14,19-hexaen-3-one; 6,7-dimethoxy-12-methyl-16,18-dioxa-12-azatetracyclo[12.7.0.0^4,^9.0^1^5,^1^9]henicosa-1(21),4,6,8,14,19-hexaen-3-one
• Synonyms: CRYPTOPINE; Cryptocavine; Thalisopyrine; Cryptopine

Database IDs

• CAS Number: 482-74-6
• PubChem SID: 162093020
• PubChem CID: 72616

CALCULATED PROPERTIES

• Acid pKa: 15.9009695
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.540743
• LogD (pH = 7.4): 2.6527765
• Log P: 2.6544094
• Molar Refractivity: 101.7283 cm^3
• Polarizability: 39.24419 Å^3
• Polar Surface Area: 57.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 220°C

Pharmacology Properties

• Mechanism of Action: Metabolic activator and chain-breaking antioxidant

Product Information

• Biological Source: Alkaloid from a variety of genera in the Fumariaceae (Corydalis, Dicentra), Papaveraceae (Argemone, Meconopsis, Papaver, Stylomecon) and Ranunculaceae (Thalictrum)
• Application(s): Possesses uterotonic props.

DETAILS

MP Biomedicals - 05201142

MP Biomedicals Rare Chemical collection

REFERENCES

• Hanus, V. et al., Coll. Czech. Chem. Comm., 1967, 32, 1759, (deriv, ms)
• Hruban, L. et al., Coll. Czech. Chem. Comm., 1967, 32, 3414, (uv)
• Hall, S.R. et al., Acta Cryst. B, 1968, 24, 346, (cryst struct)
• Brochmann-Hanssen, E. et al., Planta Med., 1970, 18, 366, (isol, deriv)
• Nakashima, T.T. et al., Org. Magn. Reson., 1973, 5, 9, (cmr)
• Sax, N.I., Dangerous Properties of Industrial Materials, 5th edn., Van Nostrand Reinhold, 1979, 522
• Haworth, R.D. et al., J.C.S., 1926, 1769, (synth)
• Dolejs, L. et al., Coll. Czech. Chem. Comm., 1964, 29, 2479, (ms)
• Ma, J.C.N. et al., Can. J. Chem., 1965, 43, 1849, (pmr)