CAS 27548-93-2

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Also known as: 27548-93-2, Baccatine iii, Chebi:32898, 40k5pz0k67, 7,11-methano-5h-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-, Baccatin cento

Molecular Formula

C₃₁H₃₈O₁₁

Molecular Weight

586.6 g/mol

InChI Key

OVMSOCFBDVBLFW-VHLOTGQHSA-N

FDA UNII

40K5PZ0K67

Baccatin III is a compound obtained from the needles of the Taxus baccata tree that is used as a precursor of paclitaxel.

1 2D Structure

CAS 27548-93-2

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

2.1.2 InChI

InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1

2.1.3 InChI Key

OVMSOCFBDVBLFW-VHLOTGQHSA-N

2.1.4 Canonical SMILES

CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)OC(=O)C

2.1.5 Isomeric SMILES

CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)OC(=O)C

2.2 Other Identifiers

2.2.1 UNII

40K5PZ0K67

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 27548-93-2

2. Baccatine Iii

3. Chebi:32898

4. 40k5pz0k67

5. 7,11-methano-5h-cyclodeca[3,4]benz[1,2-b]oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-

6. Baccatin Cento

7. Nsc 330753

8. Unii-40k5pz0k67

9. Nsc-330753

10. 13-o-de[(2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]paclitaxel (baccatin Iii)

11. 7,11-methano-5h-cyclodeca(3,4)benz(1,2-b)oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-

12. Baccatin Iii [who-dd]

13. Chembl288043

14. Schembl3118475

15. Ex-a832

16. Dtxsid301029474

17. Nitroniumhexafluoroantimonate

18. Baccatin Iii, >=95% (hplc)

19. Hy-n6985

20. Zinc4102268

21. Mfcd00153921

22. Akos024462641

23. Ccg-208344

24. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5h-cyclodeca[3,4]benz[1,2-b]oxet-5-one

25. 7,11-methano-5h-cyclodeca(3,4)benz(1,2-b)oxet-5-one, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-, (2ar-(2aalpha,4beta,4abeta,6beta,9alpha,11alpha,12alpha,12aalpha,12balpha))-

26. As-35071

27. Cs-0013149

28. 548b932

29. Q-100350

30. Q15410249

31. (2ar,4s,4as,6r,9s,11s,12s,12ar,12bs)-12-(benzoyloxy)-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1h-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2ah)-diyl Diacetate

32. [2ar-(2aalpha,4beta,4abeta,6beta,9alpha,11alpha,12alpha,12aalpha,12balpha)]-6,12b-bis(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,9,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-5h-cyclodeca(3,4)benz(1,2-b)oxet-5-one

33. 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₁H₃₈O₁₁
Molecular Weight	586.6 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Exact Mass	586.24141202 g/mol
Monoisotopic Mass	586.24141202 g/mol
Topological Polar Surface Area	166 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	1200
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1