(10S)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.02,6]dodeca-1(9),2(6),7-trien-12-one

• ChemBase ID: 179764
• Molecular Formular: C20H17NO6
• Molecular Mass: 367.35208
• Monoisotopic Mass: 367.10558727
• SMILES: c12C(=O)O[C@@H](c1ccc1c2OCO1)[C@@H]1c2c(cc3c(c2)OCO3)CCN1C
• Canonical SMILES: CN1CCc2c([C@H]1[C@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1
• InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18-/m0/s1
• InChIKey: IYGYMKDQCDOMRE-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-12-one
• IUPAC Traditional name: (10S)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^2,^6]dodeca-1(9),2(6),7-trien-12-one
• Synonyms: Adlumidine

Database IDs

• CAS Number: 550-49-2
• PubChem SID: 164235674
• PubChem CID: 120734

CALCULATED PROPERTIES

• Acid pKa: 14.719359
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.7533164
• LogD (pH = 7.4): 2.3607793
• Log P: 2.6769574
• Molar Refractivity: 93.4534 cm^3
• Polarizability: 36.674076 Å^3
• Polar Surface Area: 66.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Sigma receptor agonist

Product Information

• Biological Source: Alkaloid from many Corydalis spp. and several Fumaria spp. (opt. rotn. of isolates not recorded in some cases). Also isol. from Adlumia fungosa (Adlumia cirrhosa) (Fumariaceae, Papaveraceae)
• Application(s): Muscle relaxant; Phytoncide

REFERENCES

• Manske, R.H.F., J.A.C.S., 1950, 32, 3207, (isol, struct)
• Blha, K. et al., Coll. Czech. Chem. Comm., 1964, 29, 2328, (config)
• Snatzke, G. et al., Tetrahedron, 1969, 25, 5059, (ord, cd)
• Margvelashvili, N.N. et al., Khim. Prir. Soedin., 1972, 8, 127; 1978, 14, 592; Chem. Nat. Compd. (Engl. Transl.), 1972, 8, 131; 1978, 14, 509, (isol, ir, uv)
• Lu, S.-T. et al., J.C.S. Perkin 1, 1976, 63, (isol)
• Blasko, G. et al., J. Nat. Prod., 1982, 45, 121, (occur)
• Ribr, B. et al., Acta Cryst. C, 1991, 47, 2191, (cryst struct)