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Basic Description
| Synonyms | Vindoline | Vindolin | 2182-14-1 | (-)-Vindoline | 571PJ1LW03 | NSC91994 | NSC-91994 | SR-05000002168 | NSC-628056 | NSC 91994 | VINDOLINE [MI] | SCHEMBL234532 | UNII-571PJ1LW03 | MEGxp0_001802 | CHEMBL2001832 | ACon1_000494 | CHEBI:16380 | DTXSID901045589 | HY-N0687 | Methyl 4-(acetyloxy)-3- |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Alkaloids and derivatives
- Class Plumeran-type alkaloids
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Superclass
Alkaloids and derivatives
| Kingdom | Organic compounds |
|---|---|
| Superclass | Alkaloids and derivatives |
| Class | Plumeran-type alkaloids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Plumeran-type alkaloids |
| Alternative Parents | Carbazoles Anisoles Dialkylarylamines Alkyl aryl ethers Aralkylamines N-alkylpyrrolidines Dicarboxylic acids and derivatives Tertiary alcohols Methyl esters Amino acids and derivatives Trialkylamines Cyclic alcohols and derivatives Azacyclic compounds Carbonyl compounds Organic oxides Organopnictogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Plumeran-type alkaloid - Carbazole - Indole or derivatives - Anisole - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Alkyl aryl ether - Aralkylamine - N-alkylpyrrolidine - Benzenoid - Dicarboxylic acid or derivatives - Methyl ester - Cyclic alcohol - Tertiary alcohol - Pyrrolidine - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Ether - Organic nitrogen compound - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic oxide - Organopnictogen compound - Amine - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system. |
| External Descriptors | Indole alkaloids |
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Associated Targets(Human)
A498 (42825 Activities)
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CAKI-1 (44928 Activities)
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CCRF-CEM (65223 Activities)
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COLO 205 (50209 Activities)
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DLD-1 (17511 Activities)
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DMS-273 (14108 Activities)
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HL-60 (67320 Activities)
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HT-29 (80576 Activities)
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K562 (73714 Activities)
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KM12 (47707 Activities)
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MCF7 (126967 Activities)
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MOLT-4 (49676 Activities)
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OVCAR-3 (48710 Activities)
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OVCAR-4 (44535 Activities)
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OVCAR-5 (45555 Activities)
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OVCAR-8 (47708 Activities)
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RPMI-8226 (44974 Activities)
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RXF 393 (41971 Activities)
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SF-295 (48000 Activities)
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SK-MEL-2 (46422 Activities)
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SK-MEL-28 (48833 Activities)
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SK-MEL-5 (47095 Activities)
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SK-OV-3 (52876 Activities)
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SN12C (47755 Activities)
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SNB-19 (46794 Activities)
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SNB-78 (14240 Activities)
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U-251 (51189 Activities)
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UACC-257 (46019 Activities)
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UACC-62 (47335 Activities)
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UO-31 (46270 Activities)
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XF498 (12972 Activities)
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A549 (127892 Activities)
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NCI/ADR-RES (33767 Activities)
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EKVX (44102 Activities)
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NCI-H322M (45589 Activities)
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HCC 2998 (41480 Activities)
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HCT-116 (91556 Activities)
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HOP-18 (11577 Activities)
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HOP-92 (41141 Activities)
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NCI-H460 (60772 Activities)
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SF-268 (49410 Activities)
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IGROV-1 (47897 Activities)
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KM-20L2 (14967 Activities)
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LOX IMVI (44321 Activities)
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HOP-62 (47048 Activities)
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M19-MEL (15326 Activities)
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Malme-3M (44254 Activities)
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SNB-75 (44215 Activities)
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NCI-H226 (44470 Activities)
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NCI-H23 (49055 Activities)
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Associated Targets(non-human)
P388 (20296 Activities)
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P388/ADR (1216 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | methyl (1R,9R,10S,11R,12R,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 |
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| INCHI | InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1 |
| InChIKey | CXBGOBGJHGGWIE-ACSXSLCXSA-N |
| Smiles | CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C |
| Isomeric SMILES | CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C |
| WGK Germany | 3 |
| RTECS | CJ0120000 |
| PubChem CID | 260535 |
| Molecular Weight | 456.53 |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Molecular Weight | 456.500 g/mol |
|---|---|
| XLogP3 | 1.300 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 6 |
| Exact Mass | 456.226 Da |
| Monoisotopic Mass | 456.226 Da |
| Topological Polar Surface Area | 88.500 Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 864.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Chuxin Liang, Chang Chen, Pengfei Zhou, Lv Xu, Jianhua Zhu, Jincai Liang, Jiachen Zi, Rongmin Yu. (2018) Effect of Aspergillus flavus Fungal Elicitor on the Production of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells. MOLECULES, 23 (12): (3276). |
| 2. Zhi Liu, Hai-Long Wu, Yong Li, Hui-Wen Gu, Xiao-Li Yin, Li-Xia Xie, Ru-Qin Yu. (2016) Rapid and simultaneous determination of five vinca alkaloids in Catharanthus roseus and human serum using trilinear component modeling of liquid chromatography–diode array detection data. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1026 (114). |
| 3. Junyan Wang, Minmin Huang, Haihong Hu, Lushan Yu, Su Zeng. (2014) Pregnane X receptor-mediated transcriptional activation of UDP-glucuronosyltransferase 1A1 by natural constituents from foods and herbs. FOOD CHEMISTRY, 164 (74). |
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