(12bS)-4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol

• ChemBase ID: 177877
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: c1c(c(c2c(c1)C[C@@H]1N(C2)CCc2c1cc(c(c2)OC)O)OC)O
• Canonical SMILES: COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(OC)c(cc1)O
• InChI: InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
• InChIKey: JKPISQIIWUONPB-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12bS)-4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol
• IUPAC Traditional name: (12bS)-4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol
• Synonyms: (13aS)-5,8,13,13a-Tetrahydro-3,9-dimethoxy-6H-dibenzo[a,g]quinolizine-2,10-diol; 3,9-Dimethoxy-13aα-Berbine-2,10-diol; (-)-Stepholidine; S-Stepholidine; L-Stepholidine

Database IDs

• CAS Number: 16562-13-3
• PubChem SID: 164233787
• PubChem CID: 6917970

CALCULATED PROPERTIES

• Acid pKa: 9.813804
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.731901
• LogD (pH = 7.4): 2.8527107
• Log P: 2.8561866
• Molar Refractivity: 92.3909 cm^3
• Polarizability: 35.281284 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S686610

A tetrahydroprotoberberine agonist at dopamine D1 and antagonist at D2 receptors. It is used for preventing or treating neural diseases. The neural diseases comprise parkinsonism, schizophrenia and dyskinesia which is produced by L-DOPA or medicine to tre

REFERENCES

• Smith, B., et al.: Pharm. Res., 17, 1278 (2000)
• Shou, M., et al.: Eur. J. Pharm. Sci., 26, 151 (20050, Upton, R., et al.: Clin. Exp. Pharmacol. Physiol., 34, 695 (2000)
• Ohno, S., et al.: Drug Metab. Dispos., 37, 32 (2000)