(20S)-5,6,9,10-tetramethoxy(15,15,17,17,18,18,21,21-2H8)-16-azapentacyclo[12.7.0.02,7.08,13.016,20]henicosa-1(14),2,4,6,8,10,12-heptaene

• ChemBase ID: 179363
• Molecular Formular: C24H27NO4
• Molecular Mass: 393.47548
• Monoisotopic Mass: 393.19400835
• SMILES: c12c3c(c4c(c1ccc(c2OC)OC)CN1[C@H](C4)CCC1)ccc(c3OC)OC
• Canonical SMILES: COc1ccc2c(c1OC)c1c(c3c2CN2CCC[C@H]2C3)ccc(c1OC)OC
• InChI: InChI=1S/C24H27NO4/c1-26-19-9-7-15-17-12-14-6-5-11-25(14)13-18(17)16-8-10-20(27-2)24(29-4)22(16)21(15)23(19)28-3/h7-10,14H,5-6,11-13H2,1-4H3/t14-/m0/s1
• InChIKey: FAGLRYVRVBPJIP-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (20S)-5,6,9,10-tetramethoxy(15,15,17,17,18,18,21,21-^2H₈)-16-azapentacyclo[12.7.0.0^2,^7.0^8,^1^3.0^1^6,^2^0]henicosa-1(14),2,4,6,8,10,12-heptaene
• IUPAC Traditional name: (20S)-5,6,9,10-tetramethoxy(15,15,17,17,18,18,21,21-^2H₈)-16-azapentacyclo[12.7.0.0^2,^7.0^8,^1^3.0^1^6,^2^0]henicosa-1(14),2,4,6,8,10,12-heptaene
• Synonyms: (S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline-d8; NSC 717335-d8; NSC 76387-d8; NSTP 0G01-d8; Tylophorin-d8; (13aS)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline-d8; Tylophorine-d8; (+)-Tylophorine-d8; (+)-(S)-Tylophorine-d8

Database IDs

• PubChem SID: 164235273
• PubChem CID: 71752877

CALCULATED PROPERTIES

• Molar Refractivity: 113.8747 cm^3
• Polarizability: 46.581394 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.6364175
• LogD (pH = 7.4): 2.2844982
• Log P: 3.7683642

DETAILS

Toronto Research Chemicals - T898202

Labelled (+)-(S)-Tylophorine. (+)-(S)-Tylophorine is a a major alkaloid of Tylophora indica. (+)-(S)-Tylophorine is an immunosuppressant and inflammation inhibitor. (+)-(S)-Tylophorine showed antiproliferative activity and induction of apoptosis in tumor

REFERENCES

• Gopalakrishnan, C. et a.: Ind. J. Med. Chem., 71, 940 (1980)
• Ganguly, T.et al.: Phytomedicine, 9, 288 (1980)
• Gao, W. et al.: Cancer, Res., 64, 678 (1980)