for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Vallesiachotamine, a known monoterpene indole alkaloid, possesses anti-tumor activity.
In Vitro
Vallesiachotamine induces G0/G1 arrest and increased the proportion of sub-G1 hypodiploid cells (at 11 μM and 22 μM) and this effect is not dependent on time of incubation. Vallesiachotamine acts by promoting G0/G1 cell cycle arrest, apoptosis and necrosis. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Canonical Smiles | CC=C(C=O)C1CC2C3=C(CCN2C=C1C(=O)OC)C4=CC=CC=C4N3 |
|---|---|
| IUPAC Name | methyl (2S,12bS)-2-[(E)-1-oxobut-2-en-2-yl]-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate |
| InChIKey | NTVLUSJWJRSPSM-JXSBNBLESA-N |
| INCHI | 1S/C21H22N2O3/c1-3-13(12-24)16-10-19-20-15(14-6-4-5-7-18(14)22-20)8-9-23(19)11-17(16)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/b13-3-/t16-,19-/m0/s1 |
| Isomeric SMILES | C/C=C(/C=O)\[C@@H]1C[C@H]2C3=C(CCN2C=C1C(=O)OC)C4=CC=CC=C4N3 |
| PubChem CID | 5384527 |
| NSC Number | 338699 |
| MeSH Entry Terms | vallesiachotamine |
| Molecular Weight | 350.41 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Pyridoindoles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Beta carbolines |
| Alternative Parents | 3-alkylindoles Quinolizines Aralkylamines Tetrahydropyridines Benzenoids Vinylogous amides Pyrroles Enals Enoate esters Heteroaromatic compounds Methyl esters Amino acids and derivatives Trialkylamines Enamines Allylamines Azacyclic compounds Monocarboxylic acids and derivatives Aldehydes Hydrocarbon derivatives Organic oxides |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Beta-carboline - Quinolizine - 3-alkylindole - Indole - Aralkylamine - Tetrahydropyridine - Benzenoid - Alpha,beta-unsaturated aldehyde - Enal - Pyrrole - Heteroaromatic compound - Vinylogous amide - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Amino acid or derivatives - Carboxylic acid ester - Tertiary amine - Tertiary aliphatic amine - Monocarboxylic acid or derivatives - Allylamine - Enamine - Carboxylic acid derivative - Azacycle - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Amine - Aldehyde - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety. |
| External Descriptors | Not available |
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| Molecular Weight | 350.400 g/mol |
|---|---|
| XLogP3 | 2.700 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Exact Mass | 350.163 Da |
| Monoisotopic Mass | 350.163 Da |
| Topological Polar Surface Area | 62.400 Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 641.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |
| 1. Jianhua Zhu, Shuijie He, Pengfei Zhou, Jiachen Zi, Jincai Liang, Liyan Song, Rongmin Yu. (2018) Eliciting Effect of Catharanthine on the Biosynthesis of Vallesiachotamine and Isovallesiachotamine in Catharanthus roseus Cambial Meristematic Cells. Natural Product Communications, [PMID:] [10.1177/1934578X1801300508] |
