Aspidospermidin-3-carbonsure, 2,3,6,7-Tetradehydro-, Methylester, (5α,12β,19α)-

Tabersonine

HCID 20485CAS 4429-63-4

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Grundinformationen

Standard-SMILES: CC[C@]12C=CCN3CC[C@]4(C(=C(C(=O)OC)C1)Nc1ccccc14)[C@@H]32
InChIKey: FNGGIPWAZSFKCN-ACRUOGEOSA-N
Summenformel: C21H24N2O2
Durchschnittliche Molmasse: 336,4 g/mol
Monoisotopische Masse: 336,18377801

Überblick

Tabersonine is a monoterpenoid indole alkaloid with cytotoxic activity. It has a role as a metabolite and an antineoplastic agent. It is a methyl ester, an organic heteropentacyclic compound, an alkaloid ester and a monoterpenoid indole alkaloid. It is a conjugate base of a tabersoninium(1+).

Namen und Bezeichner

Bevorzugter Name: Tabersonine
IUPAC: methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
Lokaler Name: Aspidospermidin-3-carbonsure, 2,3,6,7-Tetradehydro-, Methylester, (5α,12β,19α)-
Englischer Name: TABERSONINE
Summenformel: C21H24N2O2
Molmasse: 336.44

Namen und Synonyme

Tabersonine4429-63-4TabersoninMN955K48NBAspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12beta,19alpha)-CHEBI:16776DTXSID30196102methyl 2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylatemethyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylatemethyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9,13-pentaene-10-carboxylateRefChem:187087DTXCID00118593

Weitere Namen anzeigen

W 873W-873C09244TabuningabersonineIt's BoninIt's BoninBRN 3051738

224-615-0(-)-TabersonineMFCD28140545Q21099578(5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid, methyl estermethyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate(-)-Tabersonine; (5|A,12|A,19|A)-2,3,6,7-Tetrahydro-aspidospermidine-3-carboxylic acid methyl ester; TabersoninASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-

Datenbank-Bezeichner

CAS: 4429-63-4
PubChem CID: 20485
DTXSID: DTXSID30196102
ChEMBL: CHEMBL2011511
ChEBI: CHEBI:16776
UNII: MN955K48NB
EC Number: 224-615-0
Nikkaji: J62.335K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,4
Polarare Oberfläche (TPSA): 41,6 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 3
Schwere Atome: 25
Formalladung: 0
Komplexität: 669

Physikochemische Eigenschaften

Schmelzpunkt: 196 °C · 196 °C
Siedepunkt: 488.7 · 488.7±45.0 °C(Predicted)
Dichte: 1.27 · 1.27±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Inert atmosphere,Store in freezer, under -20°C
Löslichkeit: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Ethyl Acetate (Slightly)
Aggregatzustand: Solid
pka: 7 · 7+-.0.60(Predicted)
Farbe: Light Yellow to Dark Yellow
Stabilität: Light Sensitive

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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)

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungThis alkaloid, found in Amsonia tabernaemontana, is difficult to obtain crystalline but the hydrochloride is readily crystallizable and has m.p. 195-6°C; [α]D - 310° (c 0.134, MeOH).

OccurrenceThe seeds of Amsonia elliptica contain this N-oxide at tabersonine.

Verwenden(-)-Tabersonine is one of the terpenoid indole alkaloids (TIAs) from Catharanthus roseus. (-)-Tabersonine shows hypotensive activity, anti-tumor activity, hypoglycemic, diuretic activity.