(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-(3-hydroxy-3-methylbutyl)butanedioate

• ChemBase ID: 169846
• Molecular Formular: C28H37NO9
• Molecular Mass: 531.59468
• Monoisotopic Mass: 531.24683177
• SMILES: O1COc2c1cc1c(c2)[C@H]2[C@@]3(N(CC1)CCC3)C=C([C@H]2OC(=O)C(CCC(O)(C)C)(CC(=O)OC)O)OC
• Canonical SMILES: COC(=O)CC(C(=O)O[C@@H]1C(=C[C@]23[C@@H]1c1cc4OCOc4cc1CCN3CCC2)OC)(CCC(O)(C)C)O
• InChI: InChI=1S/C28H37NO9/c1-26(2,32)8-9-28(33,15-22(30)35-4)25(31)38-24-21(34-3)14-27-7-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,32-33H,5-11,15-16H2,1-4H3/t23-,24-,27+,28-/m1/s1
• InChIKey: HAVJATCHLFRDHY-KSZYUSJVSA-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-(3-hydroxy-3-methylbutyl)butanedioate
• IUPAC Traditional name: harringtonine
• Synonyms: 3-[4-Methyl (2R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate]cephalotaxine; 2'R-Harringtonine; NSC 124147; Harringtonin

Database IDs

• CAS Number: 26833-85-2
• PubChem SID: 162263978
• PubChem CID: 276389

CALCULATED PROPERTIES

• Acid pKa: 12.085257
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.9206656
• LogD (pH = 7.4): -0.5686993
• Log P: 1.440102
• Molar Refractivity: 137.4739 cm^3
• Polarizability: 54.039352 Å^3
• Polar Surface Area: 123.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 79-85°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H105285

A natural product with significant antitumor activities.

REFERENCES

• Sah, N., et al.: J. Biol. Chem., 278, 20593 (2003)
• Lu, D., et al.: J. Int. Med. Res., 32, 488 (2003)
• Yunmbam, M., et al.: Oncol. Rep., 11, 833 (2003)
• Shao, S., et al.: Cell Biol. Int., 32, 893 (2003)