Methyl-(2α,5β,6α)-3,4-didehydroibogamin-18β-carboxylat
(+)-Catharanthine
Grundinformationen
- CAS
2468-21-5- Standard-SMILES
CCC1=C[C@@H]2CN3CCc4c([nH]c5ccccc45)[C@@](C(=O)OC)(C2)[C@@H]13- InChIKey
CMKFQVZJOWHHDV-NQZBTDCJSA-N- Summenformel
- C21H24N2O2
- Durchschnittliche Molmasse
- 336,4 g/mol
- Monoisotopische Masse
- 336,18377801
Überblick
Catharanthine is an organic heteropentacyclic compound and monoterpenoid indole alkaloid produced by the medicinal plant Catharanthus roseus via strictosidine. It is a methyl ester, a bridged compound, an organic heteropentacyclic compound, an alkaloid ester, a tertiary amino compound and a monoterpenoid indole alkaloid. It is a conjugate base of a catharanthine(1+).
Namen und Bezeichner
- Bevorzugter Name
- (+)-Catharanthine
- IUPAC
- methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
- Lokaler Name
- Methyl-(2α,5β,6α)-3,4-didehydroibogamin-18β-carboxylat
- Englischer Name
- Catharanthine
- Summenformel
- C21H24N2O2
- Molmasse
- 336.43
Namen und Synonyme
Catharanthine2468-21-5(+)-CatharanthineWT0YJV846J(+)-3,4-DidehydrocoronaridineCHEBI:3469DTXSID80947621methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylatemethyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8,16-pentaene-1-carboxylateRefChem:574901DTXCID401527514219-586-6
Weitere Namen anzeigen
catharanthin18-beta)-lph(+)-CATHRANTHINECatharanthine-RMCATHARANTHINE(RG)Catharanthine(AS)Catharanthine Tartrat
Catharanthine BaseMFCD01753356CHEMBL2163793Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2alpha,5beta,6alpha,18beta)-Catharanthine, (+)-(6R,6aR,9R,11R)-Methyl 7-ethyl-6,6a,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylateUNII-WT0YJV846JEINECS 219-586-6
Datenbank-Bezeichner
- CAS
2468-21-5- PubChem CID
- 5458190
- DTXSID
DTXSID80947621- ChEMBL
CHEMBL2163793- ChEBI
CHEBI:3469- UNII
- WT0YJV846J
- EC Number
- 219-586-6
- Nikkaji
- J15.154H、J2.996.318E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 45,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 603
Experimentelle und physikochemische Eigenschaften
LogP3.45
Physikochemische Eigenschaften
- Schmelzpunkt
- 138 · 138-1400C
- Siedepunkt
- 472.9 °C · 472.9°C (rough estimate)
- Dichte
- 1.1367 · 1.1367 (rough estimate)
- Brechungsindex
- 1.65 · 1.6500 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 5 mg/mL · DMSO: soluble5mg/mL (clear solution; warmed)
- Aggregatzustand
- powder
- pka
- 6.8 · 6.8(at 25℃)
- Farbe
- white to beige
- InChI
- InChI=1/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/s3
- InChIKey
- CMKFQVZJOWHHDV-XWQFPIRHNA-N
- SMILES
- [C@]12(C(=O)OC)C[C@]3([H])C=C(CC)[C@@]1([H])[N@](CCC1C4=C(C=CC=C4)NC2=1)C3 |&1:0,6,12,14,r|
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)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
Chemie und Industrie
Anwendungen
VerwendenCatharanthine is an indole alkaloid analog and an inhibitor of TRPM8.
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