10-Deacetylbaccatin III - analytical standard, ≥98% , CAS No.32981-86-5

CAS: 32981-86-5 Cat. No.: D107312 Molecular Weight: 544.59 EC Number: 608-810-1

GRADE & PURITY Analytical standard, ≥98%

Synonyms

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-4,6,9,11-tetrahydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate | MLS006011993 | SMR004703546 | BRD-K96631475-001

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

(2aR, 4S, 4aS, 6R, 9S, 11S, 12S, 12aR, 12bS)-12b-acetoxy-4, 6, 9, 11-tetrahydroxy-4a, 8, 13, 13-tetramethyl-5-oxo-2a, 3, 4, 4a, 5, 6, 9, 10, 11, 12, 12a, 12b-dodecahydro-1H-7, 11-methanocyclodeca[3, 4]benzo[1, 2-b]oxet-12-yl benzoate | MLS006011993 | SMR004703546 | BRD-K96631475-001

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

10-Deacetylbaccatin-III is an intermediate for taxol analog preparations. Taxols have exhibit antitumor agents. Several of these taxols can be synthesized from 10- Deacetylbaccatin-III. 10-Deacetylbaccine III is the fifth intermediate of

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Purity

≥98%

Names and Identifiers

• 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)O
• 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[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• InChIKey: YWLXLRUDGLRYDR-ZHPRIASZSA-N
• 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
• 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)O
• WGK Germany: 3
• Molecular Weight: 544.59
• Reaxy-Rn: 13170468
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13170468&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Taxanes and derivatives
• Alternative Parents: Benzoic acid esters Benzoyl derivatives Dicarboxylic acids and derivatives Tertiary alcohols Secondary alcohols Oxetanes Ketones Cyclic alcohols and derivatives Carboxylic acid esters Polyols Oxacyclic compounds Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Taxane diterpenoid - Benzoate ester - Benzoic acid or derivatives - Benzoyl - Monocyclic benzene moiety - Benzenoid - Dicarboxylic acid or derivatives - Cyclic alcohol - Tertiary alcohol - Carboxylic acid ester - Secondary alcohol - Ketone - Oxetane - Ether - Dialkyl ether - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Polyol - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] propellane ring system.
• External Descriptors: Diterpenes - Taxanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

A498 (42825 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-3 (62116 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SW480 (6023 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H460 (60772 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A2780 (11979 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KB (17409 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NCI-H226 (44470 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania donovani (89745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -42° (C=1,MeOH)
• Melt Point(°C): 231-236°C
• Molecular Weight: 544.600 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 544.231 Da
• Monoisotopic Mass: 544.231 Da
• Topological Polar Surface Area: 160.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 1090.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Hao Li, Wenbo Xie, Lei Zeng, Wen Li, Boan Shi, Fuhou Lei.  (2022)  Development and evaluation of a hydrogenated rosin (β-acryloxyl ethyl) ester–bonded silica stationary phase for high-performance liquid chromatography separation of paclitaxel from yew bark.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:35038614] [10.1016/j.chroma.2022.462815]

2. Jia Gao, Li Chen, Yongsheng Yan, Jian Lu, Wendong Xing, Jiangdong Dai, Minjia Meng, Yilin Wu.  (2021)  Dot-matrix-initiated molecularly imprinted nanocomposite membranes for selective recognition: a high-efficiency separation system with an anti-oil fouling layer.  Environmental Science-Nano,  8  (10): (2932-2949).  [PMID:] [10.1039/D1EN00296A]

3. Bi Wang, Shu Xu, Yan Cao, Fei Liu, Xingzeng Zhao, Xu Feng.  (2018)  Fungicidal activity of 10-deacetylbacatin III against Phytophthora capsici via inhibiting lysine biosynthesis.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:30497701] [10.1016/j.pestbp.2018.09.008]

4. Yu Chunna, Luo Xiujun, Zhan Xiaori, Hao Juan, Zhang Lei, L Song Yao-Bin, Shen Chenjia, Dong Ming.  (2018)  Comparative metabolomics reveals the metabolic variations between two endangered Taxus species (T. fuana and T. yunnanensis) in the Himalayas.  BMC PLANT BIOLOGY,  18  (1): (1-12).  [PMID:30223770] [10.1186/s12870-018-1412-4]

5. Hao Juan, Guo Hong, Shi Xinai, Wang Ye, Wan Qinghua, Song Yao-Bin, Zhang Lei, Dong Ming, Shen Chenjia.  (2017)  Comparative proteomic analyses of two Taxus species (Taxus × media and Taxus mairei) reveals variations in the metabolisms associated with paclitaxel and other metabolites.  PLANT AND CELL PHYSIOLOGY,  58  (11): (1878-1890).  [PMID:29016978] [10.1093/pcp/pcx128]

6. Yu Chunna, Guo Hong, Zhang Yangyang, Song Yaobin, Pi Erxu, Yu Chenliang, Zhang Lei, Dong Ming, Zheng Bingsong, Wang Huizhong, Shen Chenjia.  (2017)  Identification of potential genes that contributed to the variation in the taxoid contents between two Taxus species (Taxus media and Taxus mairei).  TREE PHYSIOLOGY,  37  (12): (1659-1671).  [PMID:28985439] [10.1093/treephys/tpx091]

7. Na Yang, Xingyuan Zhang, Juanqiong Ma, Liqing Ouyang, Zhiyong Xie, Pei Li, Xiao Lin, Qiongfeng Liao, Yanlong Chen.  (2025)  Synergistic integration of three-dimensional covalent organic frameworks and molecularly imprinted nanocavities for selective extraction of chiral 10-deacetylbacatin III.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:40440919] [10.1016/j.chroma.2025.466072]