Vindoline

Synopsis, Chemistry

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Also known as: Vindolin, 2182-14-1, (-)-vindoline, 571pj1lw03, Nsc91994, Nsc-91994

Molecular Formula

C₂₅H₃₂N₂O₆

Molecular Weight

456.5 g/mol

InChI Key

CXBGOBGJHGGWIE-ACSXSLCXSA-N

FDA UNII

571PJ1LW03

Vindoline is an indole alkaloid that exhibits antimitotic activity by inhibiting microtubule assembly. (NCI)

1 2D Structure

Vindoline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

CXBGOBGJHGGWIE-ACSXSLCXSA-N

2.1.4 Canonical SMILES

CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C

2.1.5 Isomeric SMILES

CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C

2.2 Other Identifiers

2.2.1 UNII

571PJ1LW03

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Vindoline, Citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer

2. Vindoline, Monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Vindolin

2. 2182-14-1

3. (-)-vindoline

4. 571pj1lw03

5. Nsc91994

6. Nsc-91994

7. Sr-05000002168

8. Nsc-628056

9. Nsc 91994

10. Vindoline [mi]

11. Schembl234532

12. Unii-571pj1lw03

13. Megxp0_001802

14. Chembl2001832

15. Acon1_000494

16. Chebi:16380

17. Dtxsid901045589

18. Hy-n0687

19. Methyl 4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

20. Methyl 4beta-acetyloxy-3beta-hydroxy-16-methoxy-1-methyl-6,7-didehydro-2beta,5alpha,12beta,19alpha-aspidospermidine-3alpha-carboxylate

21. Vindoline, >=98.0% (hplc)

22. Einecs 218-558-0

23. Mfcd27991347

24. S3970

25. Zinc53201238

26. Akos032962057

27. Ccg-208615

28. Nsc 628056

29. Smp2_000150

30. Ncgc00163666-02

31. Nci60_042033

32. Cs-0009711

33. Sr-05000002168-2

34. Sr-05000002168-3

35. Brd-k64280411-001-01-7

36. Q15427936

37. (2.beta.,3.beta.,4.beta.,5.alpha.,12.beta.,19.alpha.)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester

38. (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid

39. 57794-53-3

40. Aspidospermidine-3-carboxylic Acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, Methyl Ester, (2.beta.,3.beta.,4.beta.,5.alpha.,12r,19.alpha.)-

41. Aspidospermidine-3-carboxylic Acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, Methyl Ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-

42. Aspidospermidine-3-carboxylic Acid,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, Methyl Ester, (2.beta.,3.beta.,4.beta.,5.alpha.,12.beta.,19.alpha.)-

43. Methyl (2bet.,3bet.,4bet.,5alp.,12r,19alp.)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylate

44. Methyl (3ar,4r,5s,5ar,10br,13ar)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8- Methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1h-indolizino[8,1- Cd]carbazole-5-carboxylate

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₂N₂O₆
Molecular Weight	456.5 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	456.22603674 g/mol
Monoisotopic Mass	456.22603674 g/mol
Topological Polar Surface Area	88.5 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	864
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1