Combretastatin A4

HCID 5351344CAS 117048-59-6

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Grundinformationen

Standard-SMILES: COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1O
InChIKey: HVXBOLULGPECHP-WAYWQWQTSA-N
Summenformel: C18H20O5
Durchschnittliche Molmasse: 316,3 g/mol
Monoisotopische Masse: 316,13107374

Überblick

Combretastatin A4 is a stilbenoid.

Namen und Bezeichner

Bevorzugter Name: Combretastatin A4
IUPAC: 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
Englischer Name: COMBRETASTATIN A-4
Summenformel: C18H20O5
Molmasse: 316.35

Namen und Synonyme

Combretastatin A4117048-59-6Combretastatin A-4Combrestatin A4Combretastatin 42'-deoxycombretastatin A12-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenolNSC-61372916U6OP69RQ3,4,5-Trimethoxy-3'-hydroxy-4'-methoxystilbene1-(3,4,5-Trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)etheneDTXSID101025983

Weitere Namen anzeigen

CA4CoMbretastatin Acombretastatin A-4 (CA-4)CS-A4CS-284CRC 87-09NSC 817373NSC-817373

Phenol, 2-methoxy-5-(2-(3,4,5-trimethoxyphenyl)ethenyl)-, (Z)-NSC6137292-methoxy-5-((Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)phenolRefChem:918948DTXCID80852504NSC817373631-427-6NSC609397

Datenbank-Bezeichner

CAS: 117048-59-6
PubChem CID: 5351344
DTXSID: DTXSID101025983
ChEMBL: CHEMBL67
ChEBI: CHEBI:181391
UNII: 16U6OP69RQ
EC Number: 631-427-6
Nikkaji: J424.288B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,7
Polarare Oberfläche (TPSA): 57,2 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 6
Schwere Atome: 23
Formalladung: 0
Komplexität: 358

Experimentelle und physikochemische Eigenschaften

Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt: 84.5 · 84.5-85.5°C
Siedepunkt: 490.3 · 490.3±45.0 °C(Predicted)
Dichte: 1.184 · 1.184±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
Löslichkeit: 10 mg/mL · DMSO: >10mg/mL
pka: 9.65 · 9.65±0.10(Predicted)
Aggregatzustand: powder
Farbe: off-white
Merck: 14 · 14,2494
InChI: InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChIKey: HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES: C1(O)=CC(/C=C\C2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Sicherheitsdaten

wgk: 2
ridadr: UN 2811
hs_code: 29095000
risk_code: 23/24/25-41
hazard_code: T
safety_code: 26-36/37-39-45
hazard_class: 6.1
packing_group: Ⅲ
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesCombretastatin A4 has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid.

MeSH Pharmacological ClassificationAgents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Anwendungen · 2 Einträge

BeschreibungCombrestatin A4 (CA4) is a potent inhibitor of tubulin polymerization and displays strong inhibitory activity on tumor cell growth. Combrestatin A4 was shown to inhibit tumor growth in several cell lines including IMR32 (neuroblastoma), Hs746T (gastric carcinoma), CFPAC-1 (pancreatic carcinoma), and MCF-7 (breast cancer) with IC50 values of 2.16, 5.20, 3.46, and 18.47 nM, respectively. CA4 inhibits tubulin polymerization with an IC50 value of 2.2 μM.

VerwendenCombretastatin is a small organic molecule found in the bark of the African bush willow tree Combretum caffrum. Combretastatin-A4 Prodrug Induces Mitotic Catastrophe in Chronic Lymphocytic Leukemia Cell Line Independent of Caspase Activation and Poly(ADP-ribose) Polymerase Cleavage. A potent cytotoxic agent which strongly inhibits the polymerization of tubulin by binding to the colchicine site.