VINCRISTINE SULFATE

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Trade Names
Synonyms
Status
Molecule Category Salt-form
UNII T5IRO3534A
EPA CompTox DTXSID8044331
Parent Compound: VINCRISTINE

Structure

InChI Key AQTQHPDCURKLKT-JKDPCDLQSA-N
Smiles CC[C@]1(O)C[C@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C=O)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1.O=S(=O)(O)O
InChI
InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+;/m1./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C46H58N4O14S
Molecular Weight 923.05
AlogP 3.52
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 171.17
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 60.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR PubMed DailyMed
Protein: Tubulin
Description: Tubulin beta-4A chain
Organism : Homo sapiens
P04350 ENSG00000104833
Protein: Tubulin
Description: Tubulin beta chain
Organism : Homo sapiens
P07437 ENSG00000196230
Protein: Tubulin
Description: Tubulin alpha-3C chain
Organism : Homo sapiens
P0DPH7 ENSG00000198033
Protein: Tubulin
Description: Tubulin alpha-1B chain
Organism : Homo sapiens
P68363 ENSG00000123416
Protein: Tubulin
Description: Tubulin alpha-4A chain
Organism : Homo sapiens
P68366 ENSG00000127824
Protein: Tubulin
Description: Tubulin beta-4B chain
Organism : Homo sapiens
P68371 ENSG00000188229
Protein: Tubulin
Description: Tubulin beta-3 chain
Organism : Homo sapiens
Q13509 ENSG00000258947
Protein: Tubulin
Description: Tubulin beta-2A chain
Organism : Homo sapiens
Q13885 ENSG00000137267
Protein: Tubulin
Description: Tubulin beta-8 chain
Organism : Homo sapiens
Q3ZCM7 ENSG00000261456
Protein: Tubulin
Description: Tubulin alpha-3E chain
Organism : Homo sapiens
Q6PEY2 ENSG00000152086
Protein: Tubulin
Description: Tubulin alpha-1A chain
Organism : Homo sapiens
Q71U36 ENSG00000167552
Protein: Tubulin
Description: Tubulin alpha-1C chain
Organism : Homo sapiens
Q9BQE3 ENSG00000167553
Protein: Tubulin
Description: Tubulin beta-6 chain
Organism : Homo sapiens
Q9BUF5 ENSG00000176014
Protein: Tubulin
Description: Tubulin beta-2B chain
Organism : Homo sapiens
Q9BVA1 ENSG00000137285
Protein: Tubulin
Description: Tubulin beta-1 chain
Organism : Homo sapiens
Q9H4B7 ENSG00000101162
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 11
Assay Description Organism Bioactivity Reference
Cytotoxic activity against human tumor Aro cell line Homo sapiens 0.1 nM
Cytotoxic activity against human tumor PT45 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor C8305 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor HT-29 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor MCF-7 cell line Homo sapiens 10.0 nM
Cytotoxic activity against human tumor SW 13 cell line Homo sapiens 1.0 nM
Cytotoxic activity against human tumor Hep 3B cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor Hep G2 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor Igrov-1 cell line Homo sapiens 10.0 nM
Cytotoxic activity against human tumor Ovcar-3 cell line Homo sapiens 10.0 nM
Cytotoxic activity against human tumor NCI-H295 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor PLC/PRF/5 cell line Homo sapiens 100.0 nM
Cytotoxic activity against human tumor Mia Paca 2 cell line Homo sapiens 10.0 nM
Cytotoxicity against human SMMC7721 cells after 48 hrs Homo sapiens 26.7 ug.mL-1
Cytotoxicity against human HL60 cells after 48 hrs Homo sapiens 11.2 ug.mL-1
Cytotoxicity against human L02 cells after 48 hrs Homo sapiens 28.4 ug.mL-1
Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay Homo sapiens 2.9 nM
Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay Homo sapiens 11.0 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 100.0 nM
Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR green assay Plasmodium falciparum D10 199.53 nM
Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR green assay Plasmodium falciparum 100.0 nM
Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 50.12 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based HTS Dose Confirmation to Identify Inhibitors of of 5'UTR Stem-Loop Driven Alpha-Synuclein mRNA Translation in H4 Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1813 (Primary HTS), 1827 (Project Summary)] None 55.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Inhibitors of Luciferase Translation or Activity in H4 Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1813 (Primary HTS), 1827 (Project Summary)] None 100.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors of Luciferase Translation or Activity in H4-C Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1813 (Primary HTS), 1827 (Project Summary)] None 47.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors of 5'UTR Stem-Loop Driven Prion Protein mRNA Translation in H4-C Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1827 (Project Summary), 1813 (Primary HTS)] None 63.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Inhibitors of 5'UTR Stem-Loop Driven Prion Protein mRNA Translation in H4 Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1827 (Project Summary), 1813 (Primary HTS)] None 100.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Confirmation HTS to Identify Inhibitors of of 5'UTR Stem-Loop Driven Alpha-Synuclein mRNA Translation in H4 Neuroglioblastoma Cells. (Class of assay: confirmatory) [Related pubchem assays: 1827 (Project Summary), 1813 (Primary HTS)] None 100.0 nM
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 10.9 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus 2.81 %
Cytotoxicity against human NFF cells after 72 hrs by alamar blue assay Homo sapiens 17.0 nM
Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay Homo sapiens 15.0 nM
Cytotoxicity against human HEK cells after 72 hrs by alamar blue assay Homo sapiens 31.0 nM
Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay Homo sapiens 6.1 nM
Cytotoxicity against human HeLa cells after 72 hrs by alamar blue assay Homo sapiens 36.0 nM
Cytotoxicity against human A549 cells after 72 hrs by alamar blue assay Homo sapiens 20.0 nM
Cytotoxicity against human NFF cells assessed as inhibition of cell viability after 72 hrs by alamar blue assay Homo sapiens 16.9 nM
Cytotoxicity against human PC3 cells assessed as inhibition of cell viability after 72 hrs by alamar blue assay Homo sapiens 15.3 nM
Cytotoxicity against human HeLa cells assessed as inhibition of cell viability after 72 hrs by alamar blue assay Homo sapiens 35.8 nM
PubChem BioAssay. Luminescence-based cell-based high throughput dose response assay for inhibitors of the orphan nuclear receptor subfamily 0, group B, member 1 (DAX1; NR0B1): repression of SF-1 (NR5A1) activated StAR promoter by full-length DAX-1. (Class of assay: confirmatory) None 277.93 nM
Cytotoxicity against human KB cells after 72 hrs by SRB assay Homo sapiens 20.0 nM
Cytotoxicity against human Lu1 cells after 72 hrs by SRB assay Homo sapiens 480.0 nM
Cytotoxicity against human HepG2 cells after 72 hrs by SRB assay Homo sapiens 690.0 nM
Cytotoxicity against human MCF7 cells after 72 hrs by SRB assay Homo sapiens 510.0 nM
Antiproliferative activity against human BT549 cells after 48 hrs by MTT assay Homo sapiens 54.72 nM
Antiproliferative activity against human A549 cells after 48 hrs by MTT assay Homo sapiens 171.5 nM
Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay Homo sapiens 116.6 nM
Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay Homo sapiens 27.6 nM
Antiproliferative activity against human DU145 cells after 48 hrs by MTT assay Homo sapiens 72.3 nM
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 1.69 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 1.62 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans -0.39 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -1.83 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Staphylococcus aureus subsp. aureus -14.43 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Acinetobacter baumannii -6.71 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by Resazurin F(560/590) Escherichia coli 2.79 %

Cross References

Resources Reference
ChEBI 79401
ChEMBL CHEMBL501867
FDA SRS T5IRO3534A
KEGG C13974
PubChem 5388992
SureChEMBL SCHEMBL3710
ZINC ZINC85537024
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