Thiolutin (CHEM028309)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:22:08 UTC
Update Date2016-11-09 01:18:39 UTC
Accession NumberCHEM028309
Identification
Common NameThiolutin
ClassSmall Molecule
DescriptionA dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChEBI
AcetopyrrothinChEBI
AcetopyrrothineChEBI
N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
N-(4-Methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
FarcinicineHMDB
N-AcetylpyrrothineHMDB
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}ethanimidateGenerator
ThiolutinMeSH
Chemical FormulaC8H8N2O2S2
Average Molecular Mass228.291 g/mol
Monoisotopic Mass228.003 g/mol
CAS Registry Number87-11-6
IUPAC NameN-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide
Traditional Namethiolutin
SMILESCN1C(=O)C(NC(C)=O)=C2SSC=C12
InChI IdentifierInChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
InChI KeyMHMRAFONCSQAIA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassN-arylamides
Direct ParentN-acetylarylamines
Alternative Parents
Substituents
  • N-acetylarylamine
  • N-methylpyrrole
  • Substituted pyrrole
  • Pyrrole
  • 1,2-dithiole
  • Dithiole
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP0.82ALOGPS
logP-0.53ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.5ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.35 m³·mol⁻¹ChemAxon
Polarizability21.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-3910000000-519ee727a019d3a93d69Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-7590000000-85817f7eb87b0115bd93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0590000000-515631cb29113ba3b962Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-9200000000-f7ff9dbd9f3a2082f78fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0890000000-9e6266701a4ec9c61060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-1970000000-03b1d843e3d93fbf40bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-2900000000-2d15a380d25bc120cdf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0980000000-5f26834e99b886e3f03bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0960000000-7693ffa3bb0a88d601d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-2900000000-a10fda5b87d577f08ad2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-95faf19c58c835a83e00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-0590000000-0ab84e20d5f22fd4f7afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1920000000-229b3b69617b7784c357Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034228
FooDB IDFDB012539
Phenol Explorer IDNot Available
KNApSAcK IDC00054277
BiGG IDNot Available
BioCyc IDCPD-17934
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThiolutin
Chemspider ID6608
ChEBI ID156450
PubChem Compound ID6870
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11433393
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17036064
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17914747
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18720982
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19579057
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2262169
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24723205
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25353334
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28459440
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31601735
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=32049520
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=4583213
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=4597739
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=4604615
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6758684
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=775314
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=793624
18. Dai S, Jia Y, Wu SL, Isenberg JS, Ridnour LA, Bandle RW, Wink DA, Roberts DD, Karger BL: Comprehensive characterization of heat shock protein 27 phosphorylation in human endothelial cells stimulated by the microbial dithiole thiolutin. J Proteome Res. 2008 Oct;7(10):4384-95. doi: 10.1021/pr800376w. Epub 2008 Aug 23.
19. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.