Cytochalasin D (CHEM002647)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2010-04-16 17:41:35 UTC
Update Date2026-03-31 20:45:27 UTC
Accession NumberCHEM002647
Identification
Common NameCytochalasin D
ClassSmall Molecule
DescriptionCytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. Cytochalasin D is has been isolated from the fungi Metarrhizium anisopliae and Zygosporium masonii. It also possesses antibiotic and antitumor activity. (2, 3, 6, 7, 4)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC30H37NO6
Average Molecular Mass507.618 g/mol
Monoisotopic Mass507.262 g/mol
CAS Registry Number22144-77-0
IUPAC Name3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
Traditional Namecytochalasin D
SMILESCC1C2C(CC3=CC=CC=C3)NC(=O)C22C(\C=C\CC(C)C(=O)C(C)(O)\C=C\C2OC(C)=O)C(O)C1=C
InChI IdentifierInChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+
InChI KeySDZRWUKZFQQKKV-BBXOWAOSSA-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
  • Pyrrolidone
  • 2-pyrrolidone
  • Cyclic alcohol
  • Pyrrolidine
  • Tertiary alcohol
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • 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
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point255°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP2.89ALOGPS
logP3.12ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.85ChemAxon
pKa (Strongest Basic)-0.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.93 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity141.52 m³·mol⁻¹ChemAxon
Polarizability54.54 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, Positivesplash10-052f-0000920000-a4d6da837d4a0f2eae07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-1000900000-12817b62dfb08b33d986Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-9803700000-de30be4c4236403c3caaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2000980000-ed39f35f9110be8450b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btd-3000910000-527e1ccb6f9f25d0952cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9014400000-245b60f5fd8a1046b2afSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
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. Cytochalasin D also inhibits protein synthesis. (2, 3, 6)
MetabolismNot Available
Toxicity ValuesLD50: 18.5 mg/kg (Subcutaneous, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCytochalasin D is has been isolated from the fungi Metarrhizium anisopliae and Zygosporium masonii. (4)
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. (7)
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 LinkCytochalasin D
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6433799
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available