Fangchinoline
Grundinformationen
- CAS
436-77-1- Standard-SMILES
COc1ccc2cc1Oc1ccc(cc1)C[C@H]1c3cc(c(OC)cc3CCN1C)Oc1c(O)c(OC)cc3c1[C@H](C2)N(C)CC3- InChIKey
IIQSJHUEZBTSAT-VMPREFPWSA-N- Summenformel
- C37H40N2O6
- Durchschnittliche Molmasse
- 608,7 g/mol
- Monoisotopische Masse
- 608,288637
Überblick
Fangchinoline is a bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from Stephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity. It has a role as an antioxidant, an antineoplastic agent, a neuroprotective agent, an anti-HIV-1 agent, an anti-inflammatory agent and a plant metabolite. It is a bisbenzylisoquinoline alkaloid, an aromatic ether and a macrocycle.
Namen und Bezeichner
- Bevorzugter Name
- Fangchinoline
- IUPAC
- (1S,14S)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol
- Englischer Name
- (+)-FANGCHINOLINE
- Summenformel
- C37H40N2O6
- Molmasse
- 608.72
Namen und Synonyme
Fangchinoline436-77-1(+)-Fangchinoline7-O-Demethyltetrandrine(+)-LimacineNSC-77036(1S,14S)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol953592C3ZBJ11.388CCHEBI:132893DTXSID4089349816H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido(2',3':17,18)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolin-22-ol, 3,4,4a,5,16a,17,18,19-octahydro-12,21,26-trimethoxy-4,17-dimethyl-, (4aS,16aS)-
Weitere Namen anzeigen
Hanfangichin BHanfangchin B（Fangchinoline）Tetrandrine BFANGCHINO-LINEFangchinoline-RMFANGCHINOLINE (RG)Fangchinoline (Standard)
(1S,14S)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo(22.6.2.23,6.18,12.114,18.027,31.022,33)hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-22-ol, 3,4,4a,5,16a,17,18,19-octahydro-12,21,26-trimethoxy-4,17-dimethyl-, (4aS,16aS)-7-O-demethyl-tetrandrineRefChem:139929DTXCID501323517berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-, (1beta)-Berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-Hanfangchin B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,1
- Polarare Oberfläche (TPSA)
- 72,9 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 45
- Formalladung
- 0
- Komplexität
- 963
Physikochemische Eigenschaften
- Schmelzpunkt
- 240 · 240~242℃
- Siedepunkt
- 709.7 · 709.7±60.0 °C(Predicted)
- Dichte
- 1.204 · 1.204±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- Löslichkeit
- Soluble in chloroform and methanol;
- pka
- 9.38 · 9.38±0.20(Predicted)
- Aggregatzustand
- powder to crystal
- Farbe
- White to Orange to Green
- Wasserlöslichkeit
- slightly soluble in water
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- IIQSJHUEZBTSAT-VMPREFPWSA-N
- SMILES
- OC1C(=CC2CCN([C@@]3([H])CC4=CC=C(C(OC5=CC=C(C=C5)C[C@]5([H])N(CCC6=CC(=C(C=C65)OC=1C3=2)OC)C)=C4)OC)C)OC
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 2939.79.0000
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Anwendungen
BeschreibungA bisbenzylisoquino!ine alkaloid obtained from Limacia cuspidata (Miers.) Hook. f. et Thorn., the base crystallizes from Me2CO in the form of long, colourless needles. It is strongly laevorotatory with [α]D - 2120 (CHCI3) and has been shown to be the optical antipode of fanchinoline (q.v.).
Verwenden(+)-Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.
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