Cylindrospermopsin (T3D4232)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-08-29 05:55:52 UTC
Update Date2014-12-24 20:26:43 UTC
Accession NumberT3D4232
Identification
Common NameCylindrospermopsin
ClassSmall Molecule
DescriptionCylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria. CYN is a polycyclic uracil derivative containing guanidino and sulfate groups. It is also zwitterionic, making it highly water soluble. CYN is toxic to liver and kidney tissue and is thought to inhibit protein synthesis and to covalently modify DNA and/or RNA. It is not known whether cylindrospermopsin is a carcinogen, but it appears to have no tumour initiating activity in mice.
Compound Type
  • Amide
  • Amine
  • Bacterial Toxin
  • Ester
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H21N5O7S
Average Molecular Mass415.422 g/mol
Monoisotopic Mass415.116 g/mol
CAS Registry Number143545-90-8
IUPAC Name[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid
Traditional Name[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid
SMILES[H][C@](O)(C1=CC(O)=NC(O)=N1)[C@@]1([H])C[C@@]2([H])C[C@]([H])(OS(O)(=O)=O)[C@]([H])(C)[C@@]3([H])CN=C(N1)N23
InChI IdentifierInChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13-/m1/s1
InChI KeyInChIKey=LHJPHMKIGRLKDR-VDPNAHCISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridopyrimidines
Sub ClassNot Available
Direct ParentPyridopyrimidines
Alternative Parents
Substituents
  • Pyridopyrimidine
  • Imidazopyrimidine
  • Pyrimidone
  • 1,3-diazinane
  • Hydropyrimidine
  • Piperidine
  • Pyridine
  • Pyrimidine
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • 2-imidazoline
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Guanidine
  • Urea
  • Lactam
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carboximidamide
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Cytoplasm
  • Extracellular
  • Extracellular matrix
  • Golgi apparatus
  • Microsome
  • Microtubule
  • Perinuclear region
  • Plasma Membrane
  • Ribosome
Biofluid LocationsNot Available
Tissue Locations
  • Liver
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.62 g/LALOGPS
logP-1.1ALOGPS
logP-0.77ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area177.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.27 m³·mol⁻¹ChemAxon
Polarizability37.7 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009700000-5f604dd0552ef947ec832016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0219000000-5d36403f1159da9982d42016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-1972000000-1393c060fa2db8fa25192016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4009800000-20fb49db04738bc3bd5f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-8039000000-afd7e41b87ecc5e9f2ac2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9142000000-770dacc60e8cd6fb72212016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID42628600
ChEMBL IDCHEMBL1722002
ChemSpider ID26396261
KEGG IDC19999
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCylindrospermopsin
References
Synthesis ReferenceNot Available
MSDST3D4232.pdf
General References
  1. http://en.wikipedia.org/wiki/Cylindrospermopsin [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da