methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

• ChemBase ID: 172272
• Molecular Formular: C46H56N4O9
• Molecular Mass: 808.95824
• Monoisotopic Mass: 808.40472939
• SMILES: [C@@]123[C@H]([C@@]([C@@H]([C@]4([C@@H]1N(CC2)CC=C4)CC)OC(=O)C)(O)C(=O)OC)N(c1c3cc([C@@]2(c3c(c4c([nH]3)cccc4)CCN3C[C@]4([C@@H]([C@H](C2)C3)O4)CC)C(=O)OC)c(c1)OC)C
• Canonical SMILES: CC[C@@]12CN3CCc4c([C@@](C[C@@H]([C@H]2O1)C3)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@H]([C@]1(O)C(=O)OC)OC(=O)C)C)[nH]c1c4cccc1
• InChI: InChI=1S/C46H56N4O9/c1-8-42-16-12-18-50-20-17-44(37(42)50)30-21-31(34(55-5)22-33(30)48(4)38(44)46(54,41(53)57-7)39(42)58-26(3)51)45(40(52)56-6)23-27-24-49(25-43(9-2)36(27)59-43)19-15-29-28-13-10-11-14-32(28)47-35(29)45/h10-14,16,21-22,27,36-39,47,54H,8-9,15,17-20,23-25H2,1-7H3/t27-,36-,37+,38-,39-,42-,43+,44-,45+,46+/m1/s1
• InChIKey: LPGWZGMPDKDHEP-HLTPFJCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^4,^1^2.0^5,^1^0.0^1^6,^1^8]icosa-4(12),5,7,9-tetraene-13-carboxylate
• IUPAC Traditional name: methyl (1S,13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^4,^1^2.0^5,^1^0.0^1^6,^1^8]icosa-4(12),5,7,9-tetraene-13-carboxylate
• Synonyms: 4β-Acetoxy-3’α,4’-epoxy-3-hydroxy-16-methoxy-(4’α H)-vincaleukoblast-6-ene-23,22’-dioic Acid Dimethyl Ester Sulfate; Vinleurosine Sulfate; Lilly 32645; Leurosine Sulfate

Database IDs

• CAS Number: 54081-68-4
• PubChem SID: 164228182
• PubChem CID: 442111

CALCULATED PROPERTIES

• Acid pKa: 10.868012
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -0.888617
• LogD (pH = 7.4): 2.566241
• Log P: 4.311502
• Molar Refractivity: 220.1732 cm^3
• Polarizability: 87.11181 Å^3
• Polar Surface Area: 146.4 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L330800

A new antitumor derivative of Vinblastine; a dimeric Vinca alkaloid for cancer therapy.

REFERENCES

• Chakravarty, et al.: J. Med. Chem., 26(5)
• 638 (5)
• Christensson., et al.: Eu.r J. Biochem., 194, 755 (5)
• Mayer, et al.: J. Med. Chem., 34, 3029 (5)
• Yu, H., et al.: Clin. Biochem., 27, 75 (1994)