Cytochalasin B (T3D3667)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (7)XML
Targets (7)
Record Information
Version2.0
Creation Date2010-04-14 00:15:01 UTC
Update Date2014-12-24 20:26:19 UTC
Accession NumberT3D3667
Identification
Common NameCytochalasin B
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 B is an alkaloid isolated from the fungus Helminthosporium dermatioideum, as well as hormiscium species and rhoma species. (5, 2, 3, 10)
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(3E,5S,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
(7S,13E,16R,20R,21E)-7,20-Dihydroxy-16-methyl-10-phenyl-24-oxo[14]cytochalasa-6(12),13,21-triene-1,23-dione
(E,E)-16-Benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2H-oxacyclotetradec[2,3-d]isoindole-2,18(5H)-dione
Chemical FormulaC29H37NO5
Average Molecular Mass479.608 g/mol
Monoisotopic Mass479.267 g/mol
CAS Registry Number14930-96-2
IUPAC Name16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione
Traditional Namecytochalasen-B
SMILESCC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)\C=C\C(O)CCCC(C)C\C=C\C2C(O)C1=C
InChI IdentifierInChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+
InChI KeyInChIKey=GBOGMAARMMDZGR-LFKALUBKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassCytochalasins
Direct ParentCytochalasins
Alternative Parents
Substituents
  • Lactone cytochalasin skeleton
  • Cytochalasin
  • Isoindolone
  • Isoindoline
  • Isoindole
  • Isoindole or derivatives
  • Monocyclic benzene moiety
  • Pyrrolidone
  • Benzenoid
  • 2-pyrrolidone
  • Cyclic alcohol
  • Pyrrolidine
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen 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
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceFelted needles from acetone. (14)
Experimental Properties
PropertyValue
Melting Point221-223°C
Boiling PointNot Available
Solubility1.280 mg/L
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP4.05ALOGPS
logP4.08ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.11ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.42 m³·mol⁻¹ChemAxon
Polarizability52.61 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, Positivesplash10-03dl-0000900000-878f3c18257df92c699c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-2003900000-113bec8ef7184f11ab162016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114l-6903000000-865180a25119634311472016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-afbc43afc29bcbd93c1d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u0-0019700000-2545d40311da575625532016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6109300000-bd57090aa6bef521c99f2016-08-03View Spectrum
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. Cytochalasin B also inhibits glucose transport and platelet aggregation. It blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells. (2, 3, 10, 11)
MetabolismNot Available
Toxicity ValuesLD50: 11 mg/kg (Intraperitoneal, Rat) (12)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCytochalasin B is isolated from a fungus, Helminthosporium dermatioideum, as well as hormiscium species and rhoma species. (5)
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. Cytochalasin B also causes gradual but marked decline in intracellular levels of putrescine and spermidine. (1, 13)
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. (6)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5368686
ChEMBL IDCHEMBL56897
ChemSpider ID4519910
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCytochalasin_B
References
Synthesis ReferenceNot Available
MSDST3D3667.pdf
General References
  1. Sunkara PS, Nishioka K, Rao PN: Cytochalasin B inhibits polyamine biosynthesis in HeLa cells. Eur J Cell Biol. 1981 Dec;26(1):154-7. [7327176 ]
  2. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  3. Cooper JA: Effects of cytochalasin and phalloidin on actin. J Cell Biol. 1987 Oct;105(4):1473-8. [3312229 ]
  4. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  5. Five-year findings of the hypertension detection and follow-up program. I. Reduction in mortality of persons with high blood pressure, including mild hypertension. Hypertension Detection and Follow-up Program Cooperative Group. JAMA. 1979 Dec 7;242(23):2562-71. [490882 ]
  6. Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [15509185 ]
  7. Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
  8. The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 366
  9. Cole, R. J. and R. H. Cox. Handbook of Toxic Fungal Metabolites. New York: Academic Press, Inc., 1981., p. 281
  10. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
  11. Cytochalasin B. Wikipedia. Last Updated 16 June 2009. [Link]
  12. Fermentek Biotechnology 2009. MSDS for Cytochalasin B. [Link]
  13. Sigma Aldrich 1996. Technical Bulletin AL-126: The Cytochalasins. [Link]
  14. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Actin, alpha cardiac muscle 1
General Function:
Myosin binding
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTC1
Uniprot ID:
P68032
Molecular Weight:
42018.6 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
2. Actin, alpha skeletal muscle
General Function:
Structural constituent of cytoskeleton
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTA1
Uniprot ID:
P68133
Molecular Weight:
42050.67 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
3. Actin, aortic smooth muscle
General Function:
Protein kinase binding
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTA2
Uniprot ID:
P62736
Molecular Weight:
42008.57 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
4. Actin, cytoplasmic 1
General Function:
Tat protein binding
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTB
Uniprot ID:
P60709
Molecular Weight:
41736.37 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
5. Actin, cytoplasmic 2
General Function:
Ubiquitin protein ligase binding
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTG1
Uniprot ID:
P63261
Molecular Weight:
41792.48 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
6. Actin, gamma-enteric smooth muscle
General Function:
Atp binding
Specific Function:
Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.
Gene Name:
ACTG2
Uniprot ID:
P63267
Molecular Weight:
41876.495 Da
References
  1. Haidle AM, Myers AG: An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 ]
  2. Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
Target Details
7. Solute carrier family 2, facilitated glucose transporter member 1
General Function:
Xenobiotic transporter activity
Specific Function:
Facilitative glucose transporter. This isoform may be responsible for constitutive or basal glucose uptake. Has a very broad substrate specificity; can transport a wide range of aldoses including both pentoses and hexoses.
Gene Name:
SLC2A1
Uniprot ID:
P11166
Molecular Weight:
54083.325 Da
References
  1. Coderre PE, Cloherty EK, Zottola RJ, Carruthers A: Rapid substrate translocation by the multisubunit, erythroid glucose transporter requires subunit associations but not cooperative ligand binding. Biochemistry. 1995 Aug 1;34(30):9762-73. [7626647 ]