Baccatin III - 10mM in DMSO , CAS No.27548-93-2

CAS: 27548-93-2 Cat. No.: B422969 Molecular Weight: 586.63 EC Number: 636-675-9

GRADE & PURITY 10mM in DMSO

Synonyms

AS-35071 | Baccatin cento | OVMSOCFBDVBLFW-VHLOTGQHSA-N | BACCATIN III [WHO-DD] | CHEBI:32898 | NSC-330753 | 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-tri

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Baccatin III is the precursor to paclitaxel/ taxol. Antileukaemic and antitumor agent isolated from the bark of the Pacific yew tree (Taxus breviofolia). Baccatin III binds to tubules when they are assembled in the cell and stabilizes the polymerized form of tubules so that they remain assembled even under conditions in which microtubules dissociate into tubulin subunits. Baccatin III is also an inducer of apoptosis and shows antitumor properties in vitro
An apoptosis inducer and precursor to paclitaxel/taxol

Specifications

Synonyms

AS-35071 | Baccatin cento | OVMSOCFBDVBLFW-VHLOTGQHSA-N | BACCATIN III [WHO-DD] | CHEBI:32898 | NSC-330753 | 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-tri

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

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)OC(=O)C
• 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
• InChIKey: OVMSOCFBDVBLFW-VHLOTGQHSA-N
• 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
• 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
• WGK Germany: 3
• Molecular Weight: 586.63
• Reaxy-Rn: 25074663
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25074663&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 Tricarboxylic acids and derivatives Benzoyl derivatives Alpha-acyloxy ketones 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 - Tricarboxylic acid or derivatives - Benzoyl - Alpha-acyloxy ketone - Monocyclic benzene moiety - Benzenoid - Cyclic alcohol - Tertiary alcohol - Carboxylic acid ester - Ketone - Oxetane - Secondary alcohol - Carboxylic acid derivative - Ether - Organoheterocyclic compound - Oxacycle - Polyol - Dialkyl ether - Alcohol - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - 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: 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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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MCF7 (126967 Activities)

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SW480 (6023 Activities)

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WI-38 VA13 (346 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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A2780 (11979 Activities)

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HL (112 Activities)

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Associated Targets(non-human)

B16 (5829 Activities)

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L1210 (27553 Activities)

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P388 (20296 Activities)

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.5455-1.5475
• Melt Point(°C): 229-234°C
• Molecular Weight: 586.600 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 586.241 Da
• Monoisotopic Mass: 586.241 Da
• Topological Polar Surface Area: 166.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 1200.000
• 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. 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]

2. Fei Qiao, Hanqing Cong, Xuefei Jiang, Rongxiang Wang, Junmei Yin, Dan Qian, Zhunian Wang, Peter Nick.  (2014)  De Novo Characterization of a Cephalotaxus hainanensis Transcriptome and Genes Related to Paclitaxel Biosynthesis.  PLoS One,  9  (9): (e106900).  [PMID:25203398] [10.1371/journal.pone.0106900]

3. Yao Wang, Junhua Qiu, Chengwei Wang, Ruiyu Yang, Fuyou Guo, Tian Li, Shili Li, Lei Yang, Wei Ding.  (2026)  Sustainable Strategy of Natural trans-Anethole in Controlling Bacterial Wilt: Virulence Suppression and Beneficial Microbiome Enrichment.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41568748] [10.1021/acs.jafc.5c13627]