5-[2-(dimethylamino)ethyl]-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

• ChemBase ID: 178084
• Molecular Formular: C20H19NO6
• Molecular Mass: 369.36796
• Monoisotopic Mass: 369.12123733
• SMILES: c1(=O)c2c3c4c(o1)c(cc(c4c(=O)oc3c(cc2)OC)CCN(C)C)OC
• Canonical SMILES: COc1cc(CCN(C)C)c2c3c1oc(=O)c1c3c(oc2=O)c(cc1)OC
• InChI: InChI=1S/C20H19NO6/c1-21(2)8-7-10-9-13(25-4)18-16-14(10)20(23)27-17-12(24-3)6-5-11(15(16)17)19(22)26-18/h5-6,9H,7-8H2,1-4H3
• InChIKey: MTAWKURMWOXCEO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(dimethylamino)ethyl]-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^4,^1^6.0^1^1,^1^5]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione
• IUPAC Traditional name: 5-[2-(dimethylamino)ethyl]-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^4,^1^6.0^1^1,^1^5]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione
• Synonyms: 1-[2-(Dimethylamino)ethyl]-3,8-dimethoxy-[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione; Thaspine; NSC 688259; Taspin; Taspine

Database IDs

• CAS Number: 602-07-3
• PubChem SID: 164233994
• PubChem CID: 215159

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.89893484
• LogD (pH = 7.4): 0.79829156
• Log P: 2.1448991
• Molar Refractivity: 98.9081 cm^3
• Polarizability: 38.808117 Å^3
• Polar Surface Area: 74.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T007800

It is an alkaloid isolated from Radix et Rhizoma Leonticis. It shows various pharmaceutical properties: bacteriostatic, wound healing, cytotoxicity, immunosuppression, acetilcholinesterase inhibition, and inhibition of the activity of tumor angiogenesis.

REFERENCES

• Perdue, G.P., et al.: J. Pharm. Sci., 68, 124 (1979)
• Tsacheva, I., et al.: J. Biosci., 59, 528 (1979)
• Zhang, Y., et al.: Cancer Lett., 262 103 (1979)