Methyl (2S,2aS,3'aR,4'aR,5aR,12bR,12'bR,12'cR,15aR,15'aS,17'aS)-2',3',4,4'a,5,6,8,12'c,13,13',14,14',17',17'a-tetradecahydro-12'c-hydroxy-9'-methoxyspiro(1H,15aH-furo(2',3':7,8)indolizino(8,1-cd)carbazole-2(2aH),6'(7'H)-(4H,5H,15aH,16H)furo(2',3':7,8)indolizino(8,1-cd)pyrido(1,2,3-lm)carbazole)-7-carboxylate
Basic information
- CAS
19772-79-3- Standard SMILES
COC(=O)C1=C2Nc3ccccc3[C@@]23CCN2C[C@]4(C[C@@H]5C[C@]67CCO[C@H]6CCN6CC[C@@]8(c9cccc(OC)c9N(C4)[C@@]58O)[C@@H]67)[C@@H]4OCC[C@]4(C1)[C@H]23- InChIKey
IIMPGJMHQMBXKL-OPDPKHDKSA-N- Molecular formula
- C43H50N4O6
- Average molar mass
- 718.9 g/mol
- Monoisotopic mass
- 718.37303533
Overview
Vobtusine is a methyl ester, a vinca alkaloid, a spiro compound, an alkaloid ester, an indole alkaloid fundamental parent and a hemiaminal.
Names & identifiers
- Preferred name
- Methyl (2S,2aS,3'aR,4'aR,5aR,12bR,12'bR,12'cR,15aR,15'aS,17'aS)-2',3',4,4'a,5,6,8,12'c,13,13',14,14',17',17'a-tetradecahydro-12'c-hydroxy-9'-methoxyspiro(1H,15aH-furo(2',3':7,8)indolizino(8,1-cd)carbazole-2(2aH),6'(7'H)-(4H,5H,15aH,16H)furo(2',3':7,8)indolizino(8,1-cd)pyrido(1,2,3-lm)carbazole)-7-carboxylate
- IUPAC
- methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxyspiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazaheptacyclo[11.10.1.11,4.07,11.017,24.018,23.011,25]pentacosa-18(23),19,21-triene]-10-carboxylate
- English name
- Vobtusine
- Molecular formula
- C43H50N4O6
- Molecular weight
- 718.8803
Names & synonyms
Vobtusine19772-79-3CHEBI:10016methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxyspiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazaheptacyclo[11.10.1.11,4.07,11.017,24.018,23.011,25]pentacosa-18(23),19,21-triene]-10-carboxylateDTXSID60941546methyl (1R,1'R,7'S,11'R,12R,13'R,16S,17S,22R,24'R,25'S)-24'-hydroxy-19'-methoxyspiro(15-oxa-8,19-diazahexacyclo(10.9.1.01,9.02,7.012,16.019,22)docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazaheptacyclo(11.10.1.11,4.07,11.017,24.018,23.011,25)pentacosa-18(23),19,21-triene)-10-carboxylateRefChem:1089188DTXCID301369975243-288-5Methyl (2S,2aS,3'aR,4'aR,5aR,12bR,12'bR,12'cR,15aR,15'aS,17'aS)-2',3',4,4'a,5,6,8,12'c,13,13',14,14',17',17'a-tetradecahydro-12'c-hydroxy-9'-methoxyspiro(1H,15aH-furo(2',3':7,8)indolizino(8,1-cd)carbazole-2(2aH),6'(7'H)-(4H,5H,15aH,16H)furo(2',3':7,8)indolizino(8,1-cd)pyrido(1,2,3-lm)carbazole)-7-carboxylateNSC180540C43H50N4O6
Show more names
EINECS 243-288-5NSC 180540orb3141539CHEMBL4776327IIMPGJMHQMBXKL-OPDPKHDKSA-NHY-N8351TN11128CS-0143478
Database identifiers
- CAS
19772-79-3- PubChem CID
- 73534
- ChEMBL
CHEMBL1079128、CHEMBL4776327- ChEBI
CHEBI:10016- EC Number
- 243-288-5
- Nikkaji
- J125.678E
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 96 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 3
- Heavy atoms
- 53
- Formal charge
- 0
- Complexity
- 1,680
Physicochemical properties
- Melting point
- 302 · 302-5°C (dec.).
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A solid
Chemistry & industry
Applications
DescriptionAn alkaloid of Voacanga species, this base occurs chiefly in V. african a, v. dregii and V. obtusa. It yields clusters of colourless crystals from MeOH-CHCI3 and has [(dD - 321° (c 1.0, CHCI3). It is insoluble in most organic solvents but dissolves in CHCI3. The hydrochloride has m.p. 242-4°C; the hydro bromide, m.p. 290°C (dec.) and the picrate, m.p. 206-2100 C, decomposing at 300°C.
UsesVobtusine is an alkaloid that has been found in V. africana leaves.
Additional notes
DefinitionChEBI: Vobtusine is an indole alkaloid fundamental parent, an alkaloid ester, a vinca alkaloid, a hemiaminal, a methyl ester and a spiro compound.
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