(12R)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene

• ChemBase ID: 167022
• Molecular Formular: C20H21NO4
• Molecular Mass: 339.38504
• Monoisotopic Mass: 339.14705816
• SMILES: c1(c(cc2c(c1)c1c3[C@@H](C2)N(CCc3cc2c1OCO2)C)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)C[C@@H]1c3c2c2OCOc2cc3CCN1C
• InChI: InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m1/s1
• InChIKey: YJWBWQWUHVXPNC-CQSZACIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12R)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^2,^6.0^8,^2^0.0^1^4,^1^9]icosa-1(20),2(6),7,14,16,18-hexaene
• IUPAC Traditional name: (12R)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^2,^6.0^8,^2^0.0^1^4,^1^9]icosa-1(20),2(6),7,14,16,18-hexaene
• Synonyms: (7aR)-6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline; 9,10-Dimethoxy-1,2-(methylenedioxy)-6aβ-aporphine; (R)-6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline; (-)-Dicentrine; (R)-(-)-Dicentrine; NSC 251699; L-Dicentrine

Database IDs

• CAS Number: 28832-07-7
• PubChem SID: 162261155
• PubChem CID: 317843

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.4399817
• LogD (pH = 7.4): 2.845075
• Log P: 3.0093029
• Molar Refractivity: 94.7196 cm^3
• Polarizability: 37.88882 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D431500

A natural vascular alpha 1-adrenoceptor antagonist but less prevalent than the D-isomer. It markedly inhibits the contraction of rat stomach muscle strips induced by 5-HT, histamine, K+ and Ca2+ after high K+ depolarization, showing a non-competitive anta

REFERENCES

• Li, H. et al.: Zhong. Zhon. Zaz., 25, 426 (2000)
• Li, M. et al.: Acad. J. Kun. Med. Coll., 1003 (2000)
• Teng, C.M. et al.: Brit, J. Pharmacol., 104, 651 (2000)