Epothilone D

HCID 447865CAS 189453-10-9

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Grundinformationen

Standard-SMILES: C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1
InChIKey: XOZIUKBZLSUILX-GIQCAXHBSA-N
Summenformel: C27H41NO5S
Durchschnittliche Molmasse: 491,7 g/mol
Monoisotopische Masse: 491,27054441

Überblick

Epothilone D is an epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group. It has a role as a microtubule-stabilising agent.

Namen und Bezeichner

Bevorzugter Name: Epothilone D
IUPAC: (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
Englischer Name: Epothilone D
Summenformel: C27H41NO5S
Molmasse: 491.68

Namen und Synonyme

Epothilone D189453-10-9Desoxyepothilone b(-)-Desoxyepothilone BKOS-86212,13-Desoxyepothilone B(-)-Epothilone DEpothilon DNSC-703147KOS 86212,13-Deoxyepothilone BEpothiolone D

Weitere Namen anzeigen

Epo DCS-1161Ebomycin12,13-Deoxyepo13-Desoxyepothilone BEpothilone D (KOS-862)

DEpoB cpdNSC 703147T0358E0YUFEpothilone B, desoxy12,13-desoxyepothilone b, cisKOS862Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-R1492

Datenbank-Bezeichner

CAS: 189453-10-9
PubChem CID: 447865
DTXSID: DTXSID70880053
ChEMBL: CHEMBL96172
ChEBI: CHEBI:29579
UNII: T0358E0YUF

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 5
Polarare Oberfläche (TPSA): 125 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 2
Schwere Atome: 34
Formalladung: 0
Komplexität: 777

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt: 63 · 63-66°C
Siedepunkt: 663.7 · 663.7±55.0 °C(Predicted)
Dichte: 1.084 · 1.084±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer
Löslichkeit: Soluble in DMSO
Aggregatzustand: solid
pka: 13.47 · 13.47±0.70(Predicted)
Farbe: white to off-white
InChIKey: XOZIUKBZLSUILX-GIQCAXHBSA-N
SMILES: O1[C@H](/C(/C)=C/C2=CSC(C)=N2)CC=C(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC1=O |t:13|

Sicherheit und Regulatorisches

Gefahrenhinweise

Regulatory Information · 1 Eintrag

Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of ActionThe principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing.

MeSH Pharmacological ClassificationAgents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

Anwendungen · 1 Eintrag

BeschreibungEpothilones are microtubule-stabilizing agents with potential anti-neoplastic actions. They are natural macrolides that have high potency in both taxane-sensitive and taxane-resistant models. Epothilone D is a desoxy form of epothilone B (Item No. 10924) that inhibits the growth of a variety of cancer cells both in vitro (IC50 values range from 0.97 to 21 nM) and in mice. Epothilone D is brain penetrant and reduces neurodegeneration in aged tau transgenic mice. Effects include improved axonal transport, decreased tau neuropathology, and reduced hippocampal neuron loss. Epothilone D also rescues microtubule defects and attenuates nigrostriatal degeneration in a mouse model of Parkinson’s disease.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Epothilone B

Anbieter50 Anbieter

南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.