Cytochalasin B
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Basic Info
| Common Name | Cytochalasin B(F04919) |
| 2D Structure | |
| Description | Cytochalasins 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. (A742, A2910, A2911, L1913) |
| FRCD ID | F04919 |
| CAS Number | 14930-96-2 |
| PubChem CID | 5368686 |
| Formula | C29H37NO5 |
| IUPAC Name | None |
| InChI Key | GBOGMAARMMDZGR-LFKALUBKSA-N |
| InChI | InChI=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+ |
| Canonical SMILES | CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O |
| Isomeric SMILES | CC1CCCC(/C=C/C(=O)OC23C(/C=C/C1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O |
| Wikipedia | Cytochalasin B |
| Synonyms |
24-Oxa[14]cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-
2H-Oxacyclotetradec[2,3-d]isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-
CYTOCHALASIN B
MLS002703001
NSC107658
CHEMBL56897
GBOGMAARMMDZGR-LFKALUBKSA-N
SMR001566810
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 #
24-Oxa[14]cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7.beta.,13E,16R,20R,21E)-
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Cytochalasans |
| Subclass | Cytochalasins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cytochalasins |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 479.617 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 859 |
| Monoisotopic Mass | 479.267 |
| Exact Mass | 479.267 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 35 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 8 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.5000 |
| Human Intestinal Absorption | HIA+ | 0.9505 |
| Caco-2 Permeability | Caco2- | 0.6814 |
| P-glycoprotein Substrate | Substrate | 0.8073 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8507 |
| Non-inhibitor | 0.6558 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8557 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5128 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8557 |
| CYP450 2D6 Substrate | Non-substrate | 0.8436 |
| CYP450 3A4 Substrate | Substrate | 0.7159 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8518 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8573 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9326 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8075 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7240 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6783 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9748 |
| Non-inhibitor | 0.9190 | |
| AMES Toxicity | Non AMES toxic | 0.5830 |
| Carcinogens | Non-carcinogens | 0.9576 |
| Fish Toxicity | High FHMT | 0.9971 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9834 |
| Honey Bee Toxicity | Low HBT | 0.5382 |
| Biodegradation | Not ready biodegradable | 0.9965 |
| Acute Oral Toxicity | III | 0.4483 |
| Carcinogenicity (Three-class) | Danger | 0.4648 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5354 | LogS |
| Caco-2 Permeability | 0.4569 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.1774 | LD50, mol/kg |
| Fish Toxicity | 0.8007 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5903 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Anti-Inflammatory Polyoxygenated Steroids from the Soft Coral Lobophytum michaelae. | Mar Drugs | 2018 Mar 13 | 29534040 |
| Anti-Inflammatory Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium. | Mar Drugs | 2017 Sep 29 | 28961211 |
| Isoflavones and anti-inflammatory constituents from the fruits of Psoralea corylifolia. | Phytochemistry | 2017 Nov | 28825980 |
| Bioactive new withanolides from the cultured soft coral Sinularia brassica. | Bioorg Med Chem Lett | 2017 Aug 1 | 28648460 |
| Xanthohumol impairs glucose uptake by a human first-trimester extravillous trophoblast cell line (HTR-8/SVneo cells) and impacts the process of placentation. | Mol Hum Reprod | 2015 Oct | 26194608 |
| New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses. | Int J Mol Sci | 2015 Apr 29 | 25938967 |
| Mechanisms underlying the inhibitory effect of the feed contaminant deoxynivalenol on glucose absorption in broiler chickens. | Vet J | 2014 Oct | 25011710 |
| Comparative genotoxicity of nanosilver in human liver HepG2 and colon Caco2 cells evaluated by fluorescent microscopy of cytochalasin B-blocked micronucleus formation. | J Appl Toxicol | 2014 Nov | 24909674 |
| Deoxynivalenol induced oxidative stress and genotoxicity in human peripheral blood lymphocytes. | Food Chem Toxicol | 2014 Feb | 24355168 |
| The regulation of K- and L-cell activity by GLUT2 and the calcium-sensing receptor CasR in rat small intestine. | J Physiol | 2012 Jun 15 | 22495587 |
| Benzophenone derivatives from the fruits of Garcinia multiflora and their anti-inflammatory activity. | J Nat Prod | 2009 Feb 27 | 19203247 |
| A megalin-like receptor is involved in protein endocytosis in the midgut of an insect (Bombyx mori, Lepidoptera). | Am J Physiol Regul Integr Comp Physiol | 2008 Oct | 18635456 |
| Can electrons travel through actin microfilaments and generate oxidative stress in retinol treated Sertoli cell? | Mol Cell Biochem | 2007 Jul | 17203241 |
| Areca nut extracts reduce the intracellular reactive oxygen species and release of myeloperoxidase by human polymorphonuclear leukocytes. | J Periodontal Res | 2007 Feb | 17214642 |
| Induction of micronuclei in V79 cells after combined treatments with heterocyclic aromatic amines. | Food Chem Toxicol | 2002 Oct | 12387310 |
| Assessment of the adaptive response induced by quercetin using the MNCB peripheral blood human lymphocytes assay. | Mutagenesis | 2000 Jan | 10640534 |
| Accumulation and degradation in the endoplasmic reticulum of a truncated ER-60 devoid of C-terminal amino acid residues. | J Biochem | 2000 Feb | 10731687 |
| Reversible increase in tight junction permeability to macromolecules in rat ileal mucosa in vitro by sodium caprate, a constituent of milk fat. | Dig Dis Sci | 1998 Jul | 9690393 |
| High-fat diet reduces glucose transporter responses to both insulin and exercise. | Am J Physiol | 1994 Jan | 8304561 |
| [An inhibitory analysis of the role of the enterocyte cytoskeleton in the absorption of food substances in the small intestine]. | Fiziol Zh Im I M Sechenova | 1993 Jun | 8401654 |
Targets
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]
- 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
- Mechanism of Action:
- Cytochalasin B binds to GLUT1.
References
- 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 ]
- 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
- Mechanism of Action:
- 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. 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.
References
- 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 ]