GENTIAN VIOLET

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Trade Names
Synonyms
Status
Molecule Category Mixture
UNII J4Z741D6O5
EPA CompTox DTXSID5020653

Structure

InChI Key ZXJXZNDDNMQXFV-UHFFFAOYSA-M
Smiles CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)cc1.[Cl-]
InChI
InChI=1S/C25H30N3.ClH/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6;/h7-18H,1-6H3;1H/q+1;/p-1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H30ClN3
Molecular Weight 407.99
AlogP 4.46
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 9.49
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- 16000 - - -
Other cytosolic protein
- 5800 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 110
Unclassified protein
- 11000-15000 - - 75-93
Assay Description Organism Bioactivity Reference
Inhibitory concentration against Trypomastigotes (Y strain) of Trypanosoma cruzi Trypanosoma cruzi 100.0 ug.mL-1
Antitrypanosomal activity against Trypanosoma cruzi Y trypomastigotes Trypanosoma cruzi 7.5 ug.mL-1
NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay Plasmodium falciparum 22.13 nM
NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay Plasmodium falciparum 170.3 nM
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 264.0 nM
DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 508.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 918.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 140.0 nM
DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 535.0 nM DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 384.0 nM
DRUGMATRIX: Opiate kappa (OP2, KOP) radioligand binding (ligand: [3H] Diprenorphine) None 616.0 nM
DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 871.0 nM
DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: Poly(Glu:Tyr)) None 473.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 751.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 973.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 536.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 201.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 574.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 274.0 nM
DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 460.0 nM DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 419.0 nM
DRUGMATRIX: Tachykinin NK2 radioligand binding (ligand: [3H] SR-48968) None 560.0 nM
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 824.4 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 831.0 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 282.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 109.58 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 92.5 %
PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 528.1 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 994.1 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 513.7 nM
PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 393.9 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 185.9 nM
PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 466.5 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 470.6 nM
Antiproliferative activity against human HeLa cells Homo sapiens 400.0 nM
Antiproliferative activity against mouse tsFT210 cells Mus musculus 600.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 10.34 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control Escherichia coli 75.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control Escherichia coli 93.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.203 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.52 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.52 %

Cross References

Resources Reference
ChEBI 41688
ChEMBL CHEMBL64894
FDA SRS J4Z741D6O5
PubChem 11057
SureChEMBL SCHEMBL9171
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