Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-
Basic information
- CAS
2182-14-1- Standard SMILES
CCC12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC(C)=O)[C@@H]32- InChIKey
CXBGOBGJHGGWIE-KKFURDAFSA-N- Molecular formula
- C25H32N2O6
- Average molar mass
- 456.5 g/mol
Overview
See also: Vindoline (annotation moved to).
Names & identifiers
- Preferred name
- Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-
- IUPAC
- methyl (1R,9R,10S,11R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
- English name
- Vindoline
- Molecular formula
- C25H32N2O6
- Molecular weight
- 456.53
Names & synonyms
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-CHEMBL526546SCHEMBL29713444EX-A7779KCXBGOBGJHGGWIE-KKFURDAFSA-NAKOS032440830methyl acetoxy-ethyl-hydroxy-methoxy-methyl-[?]carboxylate(3a1R,4R,5S,5aR,10bR)-methyl 4-acetoxy-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylateMethyl (1R,9R,10S,11R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylateMethyl 4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylatevindolin(-)-Vindoline
Show more names
(2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl esterNSC 91994VINDOLINE
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 88.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 864
Physicochemical properties
- Melting point
- 163 · 163-1650C
- alpha
- 20 · D20 -18° (chloroform); D27 +42° (chloroform)
- Boiling point
- 569.8 · 569.8±50.0 °C(Predicted)
- Density
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
- pka
- 5.5 in · 5.5 in 66% DMF (Moza, Trojánek)
- form
- White to off-white crystalline powder.
- color
- White to Off-White
- InChIKey
- CXBGOBGJHGGWIE-KCXUSKTKNA-N
- SMILES
- [C@@]123CCN4CC=C[C@](CC)([C@H](OC(=O)C)[C@@](O)(C(=O)OC)[C@@]1([H])N(C1C=C(OC)C=CC2=1)C)[C@]34[H] |&1:0,7,10,15,21,33,r|
- FDA UNII
- 571 PJ1LW03 · 571PJ1LW03
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 341 · H341
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- rtecs
- CJ0120000
- hs_code
- 29339900
- risk_code
- 68
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 36/37-24/25
- Hazard statements
- H341
- Precautionary statements
- P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Applications
UsesVindoline is a novel antitumor agent.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Vindoline is a vinca alkaloid, an alkaloid ester, an organic heteropentacyclic compound, a methyl ester, an acetate ester, a tertiary amino compound and a tertiary alcohol. It is a conjugate base of a vindolinium(1+).
Related reactions
5 records
Compound notes
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