(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-yl 1-methyl (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)butanedioate

• ChemBase ID: 169933
• Molecular Formular: C29H39NO9
• Molecular Mass: 546.61391484
• Monoisotopic Mass: 546.26583667
• SMILES: O1COc2c1cc1c(c2)[C@H]2[C@@]3(N(CC1)CCC3)C=C([C@H]2OC(=O)C(CCCC(O)(C)C)(CC(=O)OC)O)O[13CH3]
• Canonical SMILES: COC(=O)CC(C(=O)O[C@@H]1C(=C[C@]23[C@@H]1c1cc4OCOc4cc1CCN3CCC2)O[13CH3])(CCCC(O)(C)C)O
• InChI: InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1/i3+1
• InChIKey: HYFHYPWGAURHIV-YPUYDMJESA-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-yl 1-methyl (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)butanedioate
• 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-yl 1-methyl (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)butanedioate
• Synonyms: Cephalotaxine-13C,d3 4-Methyl (2R)-2-Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (Ester); CGX 635-13C,d3; Ceflatonin-13C,d3; NSC 141633-13C,d3; Omacetaxine Mepesuccinate-13C,d3; Homoharringtonine-13C,d3

Database IDs

• PubChem SID: 162264065
• PubChem CID: 46781703

CALCULATED PROPERTIES

• Acid pKa: 12.090441
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.4760971
• LogD (pH = 7.4): -0.124130584
• Log P: 1.8846707
• Molar Refractivity: 142.0749 cm^3
• Polarizability: 55.87113 Å^3
• Polar Surface Area: 123.99 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H596502

Homoharringtonine (HHT) combined with some botanical drugs could induce cancer cells to resemble normal cells. HHT was prepared by a semi-synthetic method from Cephalotaxine, a major alkaloid of Cepahlotaxus species through the formation of α-ketoester ha

REFERENCES

• Baaske, D., et al.: Antimicrob. Agents Chemother., 12, 298 (1977)
• Tipping, A., et al.: Leukemia, 16, 2349 (1977)
• Marin, D., et al.: Cancer, 103, 1850 (1977)
• Levy, V., et al.: Br. J. Cancer, 95, 253 (1977)
• de Lavallade, H., et al.: Blood, 2779 (1977)