(2S,3S,6R)-4-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: 131099
• Molecular Formular: C29H39NO9
• Molecular Mass: 545.62126
• Monoisotopic Mass: 545.26248183
• SMILES: CC(C)(CCCC(CC(=O)OC)(C(=O)O[C@H]1[C@H]2c3cc4c(cc3CCN3[C@@]2(CCC3)C=C1OC)OCO4)O)O
• Canonical SMILES: COC(=O)CC(C(=O)O[C@@H]1C(=C[C@]23[C@@H]1c1cc4OCOc4cc1CCN3CCC2)OC)(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
• InChIKey: HYFHYPWGAURHIV-JFIAXGOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,6R)-4-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: omacetaxine mepesuccinate
• Synonyms: Homoharringtonine

Database IDs

• CAS Number: 26833-87-4
• MDL Number: MFCD03410264
• PubChem SID: 24895407; 162225377
• PubChem CID: 285033

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

PROPERTIES

Safety Information

• RTECS: FK0260000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - H0635

Biochem/physiol Actions
Homoharringtonine is a cytotoxic alkaloid from the evergreen tree, Cephalotaxus hainanensis. Binds to the 80S ribosome in eukaryotic cells and inhibits protein synthesis by interfering with chain elongation. Blocks progression of leukemic cells from G1 phase into S phase and from G2 phase into M phase.