(1R,14R,24R)-24-methoxy-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.02,10.04,8.015,23.018,22]pentacosa-2(10),3,8,15(23),16,18(22)-hexaene

• ChemBase ID: 177498
• Molecular Formular: C21H21NO6
• Molecular Mass: 383.39454
• Monoisotopic Mass: 383.1368874
• SMILES: N1([C@H]2[C@@H](c3c(cc4c(c3)OCO4)CC1)O[C@H](c1c2ccc2c1OCO2)OC)C
• Canonical SMILES: CO[C@@H]1O[C@@H]2c3cc4OCOc4cc3CCN([C@@H]2c2c1c1OCOc1cc2)C
• InChI: InChI=1S/C21H21NO6/c1-22-6-5-11-7-15-16(26-9-25-15)8-13(11)19-18(22)12-3-4-14-20(27-10-24-14)17(12)21(23-2)28-19/h3-4,7-8,18-19,21H,5-6,9-10H2,1-2H3/t18-,19-,21-/m1/s1
• InChIKey: XRBIHOLQAKITPP-SFHLNBCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,14R,24R)-24-methoxy-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0^2,^1^0.0^4,^8.0^1^5,^2^3.0^1^8,^2^2]pentacosa-2(10),3,8,15(23),16,18(22)-hexaene
• IUPAC Traditional name: (1R,14R,24R)-24-methoxy-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0^2,^1^0.0^4,^8.0^1^5,^2^3.0^1^8,^2^2]pentacosa-2(10),3,8,15(23),16,18(22)-hexaene
• Synonyms: (5bR,13bR,15S)-5b,6,7,8,13b,15-Hexahydro-15-methoxy-6-methyl-[1,3]dioxolo[4,5-h]-1,3-dioxolo[7,8][2]benzopyrano[3,4-a][3]benzazepine; (8β)-8-Methoxy-16-methyl-2,3:10,11-bis[methylenebis(oxy)]rheadan; Rhoeadine; Rhoeadin; (+)-Rheadine

Database IDs

• CAS Number: 2718-25-4
• PubChem SID: 164233408
• PubChem CID: 71752057

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 2.282779
• LogD (pH = 7.4): 3.0038636
• Log P: 3.0281596
• Molar Refractivity: 98.7763 cm^3
• Polarizability: 39.134567 Å^3
• Polar Surface Area: 58.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R317500

An isoquinoline alkaloid used in the therapeutic field particularly for the prevention and the treatment of pathologies implying a central and/or peripheral disorder.

REFERENCES

• Sariyar, G., et al.: J. Nat. Prod., 44, 239 (1981)
• Kalav, Y., et al.: Planta Med., 55, 488 (1981)