Combretastatin A4
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Grundinformationen
- CAS
117048-59-6- 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 StruktureigenschaftenWird ergänzt
- XLogP
- 3,7
- Polarare Oberfläche (TPSA)
- 57,2 Ų
- 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
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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
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.
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