(12bS)-3,4,10-trimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-11-ol

• ChemBase ID: 171780
• Molecular Formular: C20H23NO4
• Molecular Mass: 341.40092
• Monoisotopic Mass: 341.16270822
• SMILES: c1c(c(c2c(c1)C[C@@H]1N(C2)CCc2c1cc(c(c2)OC)O)OC)OC
• Canonical SMILES: COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(OC)c(cc1)OC
• InChI: InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1
• InChIKey: KDFKJOFJHSVROC-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12bS)-3,4,10-trimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-11-ol
• IUPAC Traditional name: tetrahydrocolumbamine
• Synonyms: (13aS)-5,8,13,13a-Tetrahydro-3,9,10-trimethoxy-6H-dibenzo[a,g]quinolizin-2-ol; Tetrahydro-columbamine; 2-O-Desmethyl-L-THP; Corydalis L; O10-Methylstepholidine; Tetrahydrocolumbamine; (-)-Isocorypalmine

Database IDs

• CAS Number: 483-34-1
• PubChem SID: 164227690
• PubChem CID: 440229

CALCULATED PROPERTIES

• Acid pKa: 10.116466
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.803128
• LogD (pH = 7.4): 2.9980814
• Log P: 3.0020807
• Molar Refractivity: 96.8732 cm^3
• Polarizability: 37.192818 Å^3
• Polar Surface Area: 51.16 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I798000

A metabolite of the isoquinoline alkaloid biosynthesis pathway.

REFERENCES

• Ding, B., et al.: J. Pharm. Biomed. Anal., 45, 219 (2007)
• Hawkins, K., et al.: Nat. Chem. Biol., 4, 564 (2007)
• Rao, G., et al.: J. Ethnopharmacol., 123, 1 (2007)