Cytochalasin J (CHEM002650)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (31)XML
Record Information
Version1.0
Creation Date2010-04-16 22:10:27 UTC
Update Date2026-04-06 10:58:14 UTC
Accession NumberCHEM002650
Identification
Common NameCytochalasin J
ClassSmall Molecule
DescriptionCytochalasin J is an exogenous solid with the formula C28H35NO5 and an average molecular weight of 465.58 g/mol. Cytochalasin J belongs to the cytochalasans, a class of alkaloids and derivatives within the organic compounds. This compound has been isolated from the fungus Phomopsis paspali and has demonstrated CNS activity. The protein targets of Cytochalasin J include actin, alpha skeletal muscle (ACTA1), actin, aortic smooth muscle (ACTA2), actin, cytoplasmic 1 (ACTB), and actin, cytoplasmic 2 (ACTG1). Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament, with one cytochalasin binding to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC28H35NO5
Average Molecular Mass465.581 g/mol
Monoisotopic Mass465.252 g/mol
CAS Registry Number56144-22-0
IUPAC NameNot Available
Traditional Name3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,15H,15bH-cycloundeca[e]isoindole-1,11-dione
SMILESCC1C2C(CC3=CC=CC=C3)NC(=O)C22C(\C=C\CC(C)C(=O)C(C)(O)\C=C\C2O)C(O)C1=C
InChI IdentifierInChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16-17,20-24,30-31,34H,3,9,15H2,1-2,4H3,(H,29,33)/b12-8+,14-13+
InChI KeyDMUBZPWTFAPROZ-KRQHZRJMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassNot Available
Direct ParentCytochalasans
Alternative Parents
Substituents
  • Carbocyclic cytochalasan skeleton
  • Cytochalasan
  • Isoindolone
  • Isoindoline
  • Isoindole
  • Isoindole or derivatives
  • Acyloin
  • Monocyclic benzene moiety
  • Benzenoid
  • 2-pyrrolidone
  • Pyrrolidone
  • Cyclic alcohol
  • Tertiary alcohol
  • Pyrrolidine
  • Carboxamide group
  • Cyclic ketone
  • Secondary carboxylic acid amide
  • Ketone
  • Lactam
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point137-139°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP2.29ALOGPS
logP2.67ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.83ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity132.37 m³·mol⁻¹ChemAxon
Polarizability50.62 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, Positivesplash10-0002-0000900000-6166edd911e8c979c438Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-2004900000-62cb9f9ca17e29c2720aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-9803000000-270a1dc60e3899a64971Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-93af0e3cf07ec39caa4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-0001900000-6a135cdbebc3b471eb93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9024200000-2d614b46a29c3eda8c8bSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
Mechanism of ToxicityCytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (2, 3, 5)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCytochalasin J is has been isolated from the fungus Phomopsis paspali. (6)
Minimum Risk LevelNot Available
Health EffectsMajor biological effects of cytochalasins include inhibition of the division of cytoplasm, reversible inhibition of cell movement, induction of nuclear extrusion, inhibition of such processes as phagocytosis, platelet aggregation and clot retraction, glucose transport, thyroid secretion, and release of growth hormone. Some cytochalasins have been shown to have developmental effects. (6)
SymptomsNot Available
TreatmentConsider activated charcoal after gastrointestinal absportion. Nitroprusside is recommended to reverse peripheral ischemia secondary to vasoconstriction and for the treatment of hypertension. Anticoagulant therapy with intravenous heparin is also recommended. (1)
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available