methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase ID: 154511
• Molecular Formular: C25H32N2O6
• Molecular Mass: 456.53138
• Monoisotopic Mass: 456.22603675
• SMILES: CC[C@@]12C=CCN3[C@@H]1[C@@]1(CC3)c3ccc(cc3N([C@H]1[C@]([C@@H]2OC(=O)C)(C(=O)OC)O)C)OC
• Canonical SMILES: COC(=O)[C@@]1(O)[C@H](OC(=O)C)[C@]2(CC)C=CCN3[C@@H]2[C@@]2([C@H]1N(C)c1c2ccc(c1)OC)CC3
• InChI: InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
• InChIKey: CXBGOBGJHGGWIE-ACSXSLCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-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-tetraene-10-carboxylate; methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• IUPAC Traditional name: vindolin
• Synonyms: (2β,3β,4β,5α,12β,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic Acid Methyl Ester; (-)-Vindoline; NSC 91994; Vindolin; Vindoline; Methyl (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylate; Vindoline

Database IDs

• CAS Number: 2182-14-1
• EC Number: 218-558-0
• PubChem SID: 162248650
• PubChem CID: 260535

CALCULATED PROPERTIES

• Acid pKa: 10.868158
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1257739
• LogD (pH = 7.4): 0.5863102
• Log P: 1.8826375
• Molar Refractivity: 122.2981 cm^3
• Polarizability: 47.688213 Å^3
• Polar Surface Area: 88.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: Powder; White to Off-White Solid
• Melting Point: 163-165°C
• Optical Rotation: [α]/D -65±3°, c = 1.5 in methanol

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: CJ0120000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 68
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H341
• GHS Precautionary statements: P281
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C25H32N2O6

DETAILS

Sigma Aldrich - 03179

Biochem/physiol Actions
Vindoline is a monoterpenoid indole alkaloid exclusive to the Madagascar periwinkle plant (Catharanthus roseus). Vindoline combines catharanthine to derive the anti-cancer agents vinblastine and vincristine.

Toronto Research Chemicals - V416500

A novel antitumor agent.

REFERENCES

• Distefano, M., et al.: Int. J. Cancer, 72, 844 (1997)
• Altstadt, T., et al.: J. Med. Chem., 44, 4577 (1997)
• Baloglu, E., et al.: Bioorg. Med. Chem., 11, 1557 (1997)