Cabazitaxel - Moligand™, ≥99% , Inhibitor of tubulin beta class I, CAS No.183133-96-2, Inhibitor of tubulin beta class I

CAS: 183133-96-2 Cat. No.: C125379 Molecular Weight: 835.93 EC Number: 680-632-7

GRADE & PURITY Moligand™, ≥99%

Synonyms

AKOS015894546 | CABAZITAXEL ACETONATE [JAN] | HY-15459 | D09755 | J-519981 | RPR 116258A | (2alpha,5beta,7beta,10beta,13alpha)-4-acetoxy-13-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-1-hydroxy-7,10-dimethoxy-9-oxo-5,20-epoxy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Cabazitaxel (XRP6258) is a semi-synthetic derivative of a natural taxoid

Specifications

Synonyms

AKOS015894546 | CABAZITAXEL ACETONATE [JAN] | HY-15459 | D09755 | J-519981 | RPR 116258A | (2alpha, 5beta, 7beta, 10beta, 13alpha)-4-acetoxy-13-(((2R, 3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-1-hydroxy-7, 10-dimethoxy-9-oxo-5, 20-epoxy

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Cabazitaxel is a semi-synthetic derivative of the natural taxoid 10-deacetylbaccatin III with potential antineoplastic activity. Cabazitaxel binds to and stabilizes tubulin, resulting in the inhibition of microtubule depolymerization and

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of tubulin beta class I

Purity

≥99%

Product Properties

• ALogP: 2.7

Names and Identifiers

• Pubchem Sid: 504764979
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764979
• Canonical Smiles: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• InChIKey: BMQGVNUXMIRLCK-OAGWZNDDSA-N
• INCHI: 1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/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]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC
• Molecular Weight: 835.93
• Reaxy-Rn: 24865959
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24865959&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 Fatty acid esters Monosaccharides Tertiary alcohols Carbamate esters Secondary alcohols Oxetanes Carboxylic acid esters Organic carbonic acids and derivatives Ketones Oxacyclic compounds Dialkyl ethers Organic oxides Organonitrogen compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Taxane diterpenoid - Benzoate ester - Benzoic acid or derivatives - Tricarboxylic acid or derivatives - Benzoyl - Fatty acid ester - Monosaccharide - Monocyclic benzene moiety - Benzenoid - Fatty acyl - Tertiary alcohol - Carbamic acid ester - Carboxylic acid ester - Carbonic acid derivative - Oxetane - Ketone - Secondary alcohol - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organooxygen compound - Organonitrogen 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: tetracyclic diterpenoid

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)

TUBB Tclin Tubulin beta chain (0 Activities)

Discover Target: TUBB

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

A-375 (9258 Activities)

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Caco-2 (12174 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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MES-SA/Dx5 (643 Activities)

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A549 (127892 Activities)

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A-431 (6446 Activities)

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NCI-H460 (60772 Activities)

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A2780 (11979 Activities)

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KB (17409 Activities)

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HeLa (62764 Activities)

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NCI-H524 (124 Activities)

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Associated Targets(non-human)

SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO > 125 mg/ml
• Melt Point(°C): 180°C
• Molecular Weight: 835.900 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 15
• Exact Mass: 835.378 Da
• Monoisotopic Mass: 835.378 Da
• Topological Polar Surface Area: 202.000 Ų
• Heavy Atom Count: 60
• Formal Charge: 0
• Complexity: 1690.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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. P. Baby Shakila, Abdurahman Hajinur Hirad, Abdullah A. Alarfaj, Samer Hasan Hussein-Al-Ali, Beza Mulugeta.  (2023)  Precise Construction of Dual-Promising Anticancer Drugs Associated with Gold Nanomaterials on Glioma Cancer Cells.  BIOINORGANIC CHEMISTRY AND APPLICATIONS,      [PMID:37920234] [10.1155/2023/8892099]

2. Chen Guo, Haoyang Yuan, Ying Yu, Zhencheng Gao, Yu Zhang, Tian Yin, Haibing He, Jingxin Gou, Xing Tang.  (2023)  FRET-based analysis on the structural stability of polymeric micelles: Another key attribute beyond PEG coverage and particle size affecting the blood clearance.  JOURNAL OF CONTROLLED RELEASE,      [PMID:37454913] [10.1016/j.jconrel.2023.07.026]

3. Jianming Gong, Renqian Feng, Xiaoqing Fu, Qi Lin, Bicheng Wu.  (2024)  Fabrication of co-delivery liposomal formulation incorporating carmustine and cabazitaxel displays improved cytotoxic potential and induced apoptosis in ovarian cancer cells.  JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION,      [PMID:39207251] [10.1080/09205063.2024.2387949]