Rhodamine 6G

Identification

Name
Rhodamine 6G
Accession Number
DB03825  (EXPT02782)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Basic red 1
  • Calcozine rhodamine 6GX
  • CI basic red 1
  • R6G
External IDs
CI 45160 / NSC-36345
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
037VRW83CF
CAS number
989-38-8
Weight
Average: 479.02
Monoisotopic: 478.2023206
Chemical Formula
C28H31ClN2O3
InChI Key
XFKVYXCRNATCOO-UHFFFAOYSA-M
InChI
InChI=1S/C28H31N2O3.ClH/c1-6-29-23-15-25-21(13-17(23)4)27(19-11-9-10-12-20(19)28(31)32-8-3)22-14-18(5)24(30-7-2)16-26(22)33-25;/h9-16,29-30H,6-8H2,1-5H3;1H/q+1;/p-1
IUPAC Name
9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-10λ⁴-xanthen-10-ylium chloride
SMILES
[Cl-].CCNC1=CC2=[O+]C3=C(C=C(C)C(NCC)=C3)C(C3=CC=CC=C3C(=O)OCC)=C2C=C1C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus haemolyticus
UAcriflavine resistance protein BNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Rhodamine 6G.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Rhodamine 6G.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Rhodamine 6G.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Rhodamine 6G.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Rhodamine 6G.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Rhodamine 6G.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Rhodamine 6G.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Rhodamine 6G.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Rhodamine 6G.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Rhodamine 6G.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Rhodamine 6G.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Rhodamine 6G.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
KEGG Compound
C11177
ChemSpider
16740341
ChEBI
52672
HET
RHQ
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility2E+004 mg/LGREEN,FJ (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.000496 mg/mLALOGPS
logP6.36ALOGPS
logP6.71ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.72ChemAxon
pKa (Strongest Basic)2.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.5 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.49 m3·mol-1ChemAxon
Polarizability52.04 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7376
Blood Brain Barrier+0.6795
Caco-2 permeable-0.5964
P-glycoprotein substrateSubstrate0.5805
P-glycoprotein inhibitor IInhibitor0.732
P-glycoprotein inhibitor IIInhibitor0.9654
Renal organic cation transporterNon-inhibitor0.7894
CYP450 2C9 substrateNon-substrate0.7886
CYP450 2D6 substrateNon-substrate0.763
CYP450 3A4 substrateNon-substrate0.5354
CYP450 1A2 substrateInhibitor0.7318
CYP450 2C9 inhibitorInhibitor0.5489
CYP450 2D6 inhibitorNon-inhibitor0.6169
CYP450 2C19 inhibitorInhibitor0.6843
CYP450 3A4 inhibitorNon-inhibitor0.5394
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8769
Ames testNon AMES toxic0.8768
CarcinogenicityCarcinogens 0.7764
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity2.4983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9642
hERG inhibition (predictor II)Inhibitor0.6637
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Xanthenes
Alternative Parents
Benzoic acid esters / Benzoyl derivatives / Secondary alkylarylamines / Heteroaromatic compounds / Carboxylic acid esters / Amino acids and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
Xanthene / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Secondary aliphatic/aromatic amine / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound / Amino acid or derivatives / Carboxylic acid ester
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic chloride salt, rhodamine 6G(1+), xanthene dye (CHEBI:52672 )

Targets

Kind
Protein
Organism
Staphylococcus haemolyticus
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from...
Gene Name
qacR
Uniprot ID
P0A0N5
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), a...
Gene Name
acrB
Uniprot ID
P31224
Uniprot Name
Multidrug efflux pump subunit AcrB
Molecular Weight
113572.75 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Saengkhae C, Loetchutinat C, Garnier-Suillerot A: Kinetic analysis of rhodamines efflux mediated by the multidrug resistance protein (MRP1). Biophys J. 2003 Sep;85(3):2006-14. [PubMed:12944313 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 11:09