Cylindrospermopsin (CHEM003192)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-08-29 05:55:52 UTC
Update Date2016-11-09 01:09:04 UTC
Accession NumberCHEM003192
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.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Bacterial Toxin
  • Ester
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7-EpicylindrospermopsinMeSH
7-Epi-cylindrospermopsinMeSH
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 KeyLHJPHMKIGRLKDR-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
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009700000-5f604dd0552ef947ec83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0219000000-5d36403f1159da9982d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-1972000000-1393c060fa2db8fa2519Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4009800000-20fb49db04738bc3bd5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-8039000000-afd7e41b87ecc5e9f2acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9142000000-770dacc60e8cd6fb7221Spectrum
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCylindrospermopsin
Chemspider IDNot Available
ChEBI ID88044
PubChem Compound ID42628600
Kegg Compound IDC19999
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available