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Epothilone A

Epothilone A structure

CAS No:
152044-53-6
Formula:
C26H39NO6S
Chemical Name:
Epothilone A
Synonyms:
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione,7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-,(1S,3S,7S,10R,11S,12S,16R)-;4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione,7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-,[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]-;(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione;Epothilone A;(-)-Epothilone A;Epo A;186692-57-9
Categories:
Biochemical Engineering > Inhibitors

Description

Epothilone A is a competitive inhibitor of the binding of [3H] paclitaxel to tubulin polymers, with a Ki of 0.6-1.4 μM.

Epothilone A is an epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). It has a role as an antineoplastic agent, a tubulin modulator, a metabolite and a microtubule-stabilising agent. It is an epoxide and an epothilone.|Epothilone A is an extract from the myxobacteria Sorangium cellulosum that promotes tubulin polymerization and microtubule stabilization, thereby inhibiting mitosis. Epothilone A appears to be less potent than Epothilone B. (NCI)

Epothilone A Basic Attributes

Molecular Weight：

493.659

Exact Mass：

493.66

UNII：

51E07YBX96

NSC Number：

684362

DSSTox ID：

DTXSID10332288

NCI Thesaurus Code：

C1622

Characteristics

PSA：

138

XLogP3：

2.54

Density：

1.1±0.1 g/cm3

Melting Point：

95 °C @ Solvent: Ethyl acetate, Hexane

Boiling Point：

683.3±55.0 °C at 760 mmHg

Flash Point：

367.1±31.5 °C

Refractive Index：

1.532

Storage Conditions：

-20°C

Vapor Pressure：

1.31E-19mmHg at 25°C

Specific rotation：

D21 -47.1° (c = 1.0 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

Drug Information

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)

MeSH Entry Terms：

epothilon A

Epothilone A Use and Manufacturing

Uses

Epothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumor agent.

Use Classification：

Polyketides [PK] -> Macrolides and lactone polyketides [PK04]

Computed Properties

Molecular Weight:493.7
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:493.24980914
Monoisotopic Mass:493.24980914
Topological Polar Surface Area:138
Heavy Atom Count:34
Complexity:770
Defined Atom Stereocenter Count:7
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Epothilone A

CAS No.: 152044-53-6

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