CAS 32981-86-5|10-DAB|10-Deacetylbaccatin|10-deacetylbaccatin|(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4...

General Information

Structure

Molecular Formula

C₂₉H₃₆O₁₀

Molecular Mass

544.59014

Exact Mass

544.23084735

Charge

InChI

InChI=1S/C29H36O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,17-19,21-22,24,31-33,36H,11-13H2,1-5H3/t17-,18-,19+,21+,22-,24-,27+,28-,29+/m0/s1

InChIKey

YWLXLRUDGLRYDR-ZHPRIASZSA-N

Canonic Smiles

CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O

Isomeric Smiles

[C@@]12([C@@H]([C@]3([C@@H](C[C@@H]1O)OC3)OC(=O)C)[C@@H]([C@]1(C(C(=C([C@H](C1)O)C)[C@H](C2=O)O)(C)C)O)OC(=O)c1ccccc1)C

Calculated Properties

JChem

Acid pKa

10.294341

H Acceptors

H Donor

LogD (pH = 5.5)

0.6015966

LogD (pH = 7.4)

0.6010504

Log P

0.6016035

Molar Refractivity

136.1971

Polarizability

54.406586

Polar Surface Area

159.82

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

Synonyms

10-DAB10-Deacetylbaccatin10-Deacetylbaccatin III from Taxus baccata10-Deacetylbaccatin III10-DAB(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one10-Deacetyl Baccatin III

IUPAC Traditional name

10-deacetylbaccatin

IUPAC name

(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

PubChem CID

MDL Number

Registration numbers

Properties

Product Information

Safety Information

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2409

Research Area: cancer
Biological Activity:
10-DAB (10-Deacetylbaccatin) is an antineoplastic agent and an anti-cancer intermediate. 10-DAB (10-Deacetylbaccatin) has gained great attention because of its partly excellent anti-cancer properties. 10-DAB (10-Deacetylbaccatin) can be gained from the leaves of yew trees and 10-DAB (10-Deacetylbaccatin) is used as starting materials for numerous partial syntheses. The esterification of 10-DAB (10-Deacetylbaccatin) with longchain fatty acids can also generate an important enhancement of their kinetics and consequently their pharmacological action pattern. 10-DAB (10-Deacetylbaccatin) was first succinylated by use of dimethylaminopyridine and succinic anhydride in dried pyridine. [1][2]References on 10-DAB (10-Deacetylbaccatin)[1] Nat Prod Res. , 2006 Feb, 20(2):119-24[2] Biol Pharm Bull. , 2011, 34(4):562-6

Sigma Aldrich

D3676

Biochem/physiol Actions
10-Deacetylbaccine III is the fifth intermediate of paclitaxel biosynthesis. The biosynthetic pathway consists of approximately 20 enzymatic steps but is not fully elucidated1.
Application
10-Deacetylbaccatin III is used as a chemical intermediate in the preparation of the anti-cancer drug paclitaxel (Taxol). It is used to study the taxol biosynthetic pathway1,2,3.

TRC

D198250

10-Deacetyl Baccatin III is an impurity of Paclitaxel (P132500) and derivatives.

Molecule Details

References

PubChem Literature

From Data Sources

• Muto S et al. Biol Pharm Bull. 2011; 34(4):562-6.

• Sun, D., et al.: Bioorg. Med. Chem., 9, 1985 (1997)

• Hu, S., et al.: Biocatal. Biotransform., 14, 241 (1997)

References

Bioactivity