7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^{4,9}.0^{16,20}]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one

• ChemBase ID: 112417
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 369.15762284
• SMILES: COc1c(OC)c2c(CC(=O)c3cc4c(OCO4)cc3CCN(C)C2)cc1
• Canonical SMILES: COc1c(OC)ccc2c1CN(C)CCc1c(C(=O)C2)cc2c(c1)OCO2
• InChI: InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
• InChIKey: HYBRYAPKQCZIAE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^{4,9}.0^{16,20}]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one; 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^4,^9.0^1^6,^2^0]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• IUPAC Traditional name: β-allocryptopine; 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^4,^9.0^1^6,^2^0]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one
• Synonyms: ALLOCRYPTOPINE; Alpha-Fagarine; Gamma-Homochelidonine; Beta-Homochelidonine; Allocryptopine; 3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[c]azecin-14(15H)-one

Database IDs

• CAS Number: 485-91-6; 24240-04-8
• PubChem SID: 162098280
• PubChem CID: 98570

CALCULATED PROPERTIES

• Acid pKa: 15.98228
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.5328574
• LogD (pH = 7.4): 2.652647
• Log P: 2.6544094
• Molar Refractivity: 101.7283 cm^3
• Polarizability: 39.244293 Å^3
• Polar Surface Area: 57.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Pharmacology Properties

• Mechanism of Action: Potassium outward current inducer

Product Information

• Purity: 98.0
• Biological Source: Alkaloid from a wide variety of genera in the Fumariaceae ( Corydalis, Dactylicapnos ), Papaveraceae ( Argemone, Bocconia, Eschscholtzia, Glaucium, Hunnemannia, Hylomecon, Macleaya, Meconopsis, Papaver, Sanguinaria,
• Application(s): Antiarrhythmic; Antihypertensive agent; Cardiac inhibitor; Muscle relaxant; Respiratory stimulant

DETAILS

MP Biomedicals - 05223801

MP Biomedicals Rare Chemical collection

REFERENCES

• Ma, J.C.N. et al., Can. J. Chem., 1965, 43, 1849, (pmr)
• Hruban, L. et al., Coll. Czech. Chem. Comm., 1967, 32, 3414, (uv)
• Teitel, S. et al., Helv. Chim. Acta, 1973, 56, 553, (synth)
• Nakashima, T.T. et al., Org. Magn. Reson., 1973, 5, 9, (cmr)
• Battersby, A.R. et al., J.C.S. Perkin 1, 1975, 1147, (biosynth)
• Hanaoka, M. et al., Heterocycles, 1976, 4, 1685, (synth)
• Iwasa, K. et al., J.O.C., 1982, 47, 4275, (pmr, cmr)
• Sakai, T. et al., Acta Cryst. C, 1988, 44, 838, (cryst struct)
• Marek, J. et al., Coll. Czech. Chem. Comm., 1998, 63, 416-424, (cryst struct)
• Haworth, R.D. et al., J.C.S., 1926, 445, (synth)
• Deulofeu, V. et al., J.O.C., 1947, 12, 217, (struct)
• Redemann, C.E. et al., J.A.C.S., 1949, 71, 1030, (uv, struct)
• Dolejs, L. et al., Coll. Czech. Chem. Comm., 1964, 29, 2479, (ms)