(2S,3S,6R)-4-(13C,2H3)methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-ol

• ChemBase ID: 163983
• Molecular Formular: C18H21NO4
• Molecular Mass: 316.35629484
• Monoisotopic Mass: 316.150413
• SMILES: O1COc2c1cc1c(c2)[C@H]2[C@@]3(N(CC1)CCC3)C=C([C@H]2O)O[13CH3]
• Canonical SMILES: [13CH3]OC1=C[C@]23[C@@H]([C@@H]1O)c1cc4OCOc4cc1CCN3CCC2
• InChI: InChI=1S/C18H21NO4/c1-21-15-9-18-4-2-5-19(18)6-3-11-7-13-14(23-10-22-13)8-12(11)16(18)17(15)20/h7-9,16-17,20H,2-6,10H2,1H3/t16-,17-,18+/m1/s1/i1+1
• InChIKey: YMNCVRSYJBNGLD-GWXHSKSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,6R)-4-(^1^3C,^2H₃)methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^2,^6.0^6,^1^0.0^1^5,^1^9]icosa-1(20),4,13,15(19)-tetraen-3-ol
• IUPAC Traditional name: (2S,3S,6R)-4-(^1^3C,^2H₃)methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^2,^6.0^6,^1^0.0^1^5,^1^9]icosa-1(20),4,13,15(19)-tetraen-3-ol
• Synonyms: [1S-(1α,3aS*,14bβ)]-1,5,6,8,9,14b-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepin-1-ol-13Cd3; (-)-Cephalotaxine-13Cd3; NSC 128487-13Cd3; NSC 245454-13Cd3; Cephalotaxine-13C,d3

Database IDs

• PubChem SID: 162258118
• PubChem CID: 46780960

CALCULATED PROPERTIES

• Acid pKa: 13.51283
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -2.2385192
• LogD (pH = 7.4): -0.80307955
• Log P: 1.0830482
• Molar Refractivity: 86.4978 cm^3
• Polarizability: 33.31152 Å^3
• Polar Surface Area: 51.16 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C261052

Antiviral and antitumor agent.

REFERENCES

• Sells, M., et al.: J. Virol., 62, 2836 (1988)
• Kaneko, S., et al.: J. Clin. Microbiol., 27, 1930 (1988)
• Baba, Y., et al.: Bioorg. Med. Chem., 13, 5164 (1988)
• Romero, M., et al.: Antiviral Res., 68, 75 (2005)