Ptaquiloside (CHEM003053)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:07:16 UTC
Update Date2026-05-20 18:27:45 UTC
Accession NumberCHEM003053
Identification
Common NamePtaquiloside
ClassSmall Molecule
DescriptionPtaquiloside is the major toxin of bracken, and was first isolated in 1983. It is an unstable glucoside containing a reactive cyclopropane ring. (1).
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Braxin CKegg
Aquilide aMeSH
Chemical FormulaC20H30O8
Average Molecular Mass398.447 g/mol
Monoisotopic Mass398.194 g/mol
CAS Registry Number87625-62-5
IUPAC NameNot Available
Traditional Name(2'R,4'S,7'aR)-4'-hydroxy-2',4',6'-trimethyl-7'a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2',3'a-dihydro-1'H-spiro[cyclopropane-1,5'-indene]-3'-one
SMILES[H][C@@]1(C)C[C@@]2(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)C=C(C)C3(CC3)[C@@](C)(O)C2([H])C1=O
InChI IdentifierInChI=1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16?,17+,18+,20-/m1/s1
InChI KeyGPHSJPVUEZFIDE-VGFVQWJBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
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 Solubility7.3 g/LALOGPS
logP-0.59ALOGPS
logP-0.72ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.15 m³·mol⁻¹ChemAxon
Polarizability40.11 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m1-1098000000-ca8b581f10197fc6b573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2191000000-3a6330fa103679927e32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9140000000-d6235b75ec60db64620bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1169000000-96dffd0bf7bec588406dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1192000000-d6cf9576f1e81ffc7599Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-9280000000-9ca0e973173db264d1beSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (2)
Uses/SourcesPtaquiloside is the major toxin of bracken, and was first isolated in 1983.
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 IDC00021448
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID82527
PubChem Compound ID53297436
Kegg Compound IDC19515
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available