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Cerberin

HCID 10031063
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
25633-33-4
Standard-SMILES
CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)[C@H]1OC(C)=O
InChIKey
UYQMTWMXBKEHJQ-IVHDSYOHSA-N
Summenformel
C32H48O9
Durchschnittliche Molmasse
576,7 g/mol
Monoisotopische Masse
576,3298331

Überblick

Cerberin is a cardenolide glycoside that is the 2'-acetyl derivative of neriifolin. It has a role as a metabolite and an antineoplastic agent. It is a cardenolide glycoside, an acetate ester and a monosaccharide derivative. It is functionally related to a neriifolin.

Namen und Bezeichner

Bevorzugter Name
Cerberin
IUPAC
[(2R,3S,4R,5S,6S)-5-hydroxy-2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetate
Englischer Name
cerberin
Summenformel
C32H48O9
Molmasse
576.72

Namen und Synonyme

Cerberin25633-33-42'-acetylneriifolinVeneniferinKW5A155S64[(2R,3S,4R,5S,6S)-5-hydroxy-2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-6-methyloxan-3-yl] acetateCHEBI:75049DTXSID30893922((2R,3S,4R,5S,6S)-5-hydroxy-2-(((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-yl)oxy)-4-methoxy-6-methyloxan-3-yl) acetateRefChem:918244DTXCID3013239613-((4-0-acetyl-6-deoxy-3-0-methyl-alpha-L-glucopyranosyl)oxy)-14-hydroxy-(3 beta,5 beta)-card-20(22)-enolide
Weitere Namen anzeigen
Vaneferine3β-(2-O-Acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyloxy)-14-hydroxy-5β-card-20(22)-enolide3β-[(2-O-Acetyl-3-O-methyl-6-deoxy-α-L-glucopyranosyl)oxy]-14-hydroxy-5β-card-20(22)-enolide3β-(2-O-Acetyl-3-O-methyl-6-deoxy-α-L-glucopyranosyloxy)-14β-hydroxy-5β-carda-20(22)-enolide

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,7
Polarare Oberfläche (TPSA)
121 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
6
Schwere Atome
41
Formalladung
0
Komplexität
1.080

Physikochemische Eigenschaften

Schmelzpunkt
212 · 212-215 °C
Siedepunkt
693.7 · 693.7±55.0 °C(Predicted)
Dichte
1.26 · 1.26±0.1 g/cm3(Predicted)
storage temp.
Hygroscopic, Refrigerator, under inert atmosphere
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
13.06 · 13.06±0.70(Predicted)
Farbe
White to Pale Yellow
Stabilität
Hygroscopic

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

Cerbera odollam is a plant species of the Apocynaceae family and te common names include Pong-Pong and Othalanga. The poison rich part is the kernel, which is present at the core of its fruit, and the bioactive toxin is cerberin, a cardiac glycoside. Cerberin has a mechanism of action similar to digoxin, and the signs of toxicity are similar to acute digoxin poisoning. Ingestion of the kernel causes nausea, vomiting, hyperkalemia, thrombocytopenia, and ECG abnormalities, and exposure to high doses can be fatal. The initial management includes supportive therapy and the administration of atropine, followed by temporary pacemaker insertion. Administration of digoxin immune Fab can be considered in severe cases, although the authors noted hat the efficacy is variable and the data are limited to isolated case reports.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

Cerberin has a mechanism of action similar to digoxin. Thus, cerbera odollam's signs of toxicity are similar to acute digoxin poisoning. The ingestion of its kernel causes nausea, vomiting, hyperkalemia, thrombocytopenia, and ECG abnormalities.

Cerberin (CR) was found to potently inhibit cancer cell growth, colony formation and migration. Also, CR significantly increased the generation of reactive oxygen species (ROS) producing DNA double strand breaks. Preliminary in silico biopharmaceutical assessment of CR predicted >60% bioavailability and rapid absorption. The authors noted that CR's potent and selective anti-tumour activity, and its targeting of key signalling mechanisms pertinent to tumourigenesis support further preclinical evaluation of this cardiac glycoside.

Anbieter6 Anbieter

安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A cardenolide glycoside that is the 2'-acetyl derivative of neriifolin.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Card-20(22)-enolide, 3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-, (3β,5β)-
[(2S,3S,4S,5S,6R)-5-Hydroxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyloxan-3-yl] acetatePveneniferinAcetylneriifolinCard-20(22)-enolide, 3-[(2-O-acetyl-6-deoxy-3-O-methyl-.alpha.-L-glucopyranosyl)oxy]-14-hydroxy-, (3.beta.,5.beta.)-Neriifolin-monoacetatPveneniferin [German]Acetylneriifolin [German]UNII-KW5A155S64

Datenbank-Bezeichner

CAS
25633-33-4
PubChem CID
10031063
DTXSID
DTXSID30893922
ChEMBL
CHEMBL554969
ChEBI
CHEBI:75049
UNII
KW5A155S64
Nikkaji
J18.711I