Cytochalasin D
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Cytochalasin D(F04929) |
| 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 D is has been isolated from the fungi Metarrhizium anisopliae and Zygosporium masonii. It also possesses antibiotic and antitumor activity. (A2910, A2911, L1913, L1916, A2912) |
| FRCD ID | F04929 |
| CAS Number | 22144-77-0 |
| PubChem CID | 6433799 |
| Formula | C30H37NO6 |
| IUPAC Name | None |
| InChI Key | SDZRWUKZFQQKKV-BBXOWAOSSA-N |
| InChI | InChI=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+ |
| Canonical SMILES | CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O |
| Isomeric SMILES | CC1C/C=C/C2C(C(=C)C(C3C2(C(/C=C/C(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O |
| Wikipedia | Cytochalasin D |
| Synonyms |
1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
cytochalasin D
Zygosporin A
Cytohalasin D
Lygosporin A
C30H37NO6
HSDB 3549
EINECS 244-804-1
NSC 209835
(11)Cytochalasa-6(12),13,19-triene-1,17-dione, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Cytochalasans |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cytochalasans |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 507.627 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Complexity | 996 |
| Monoisotopic Mass | 507.262 |
| Exact Mass | 507.262 |
| XLogP | 2.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 37 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 9 |
| 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+ | 0.6472 |
| Human Intestinal Absorption | HIA+ | 0.9065 |
| Caco-2 Permeability | Caco2- | 0.6298 |
| P-glycoprotein Substrate | Substrate | 0.7281 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8538 |
| Inhibitor | 0.7381 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8704 |
| Distribution | ||
| Subcellular localization | Plasma membrane | 0.8351 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8237 |
| CYP450 2D6 Substrate | Non-substrate | 0.8470 |
| CYP450 3A4 Substrate | Substrate | 0.7255 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7013 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7137 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7111 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9935 |
| Non-inhibitor | 0.8811 | |
| AMES Toxicity | Non AMES toxic | 0.7050 |
| Carcinogens | Non-carcinogens | 0.9015 |
| Fish Toxicity | High FHMT | 0.9894 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9860 |
| Honey Bee Toxicity | High HBT | 0.5781 |
| Biodegradation | Not ready biodegradable | 0.9965 |
| Acute Oral Toxicity | III | 0.3412 |
| Carcinogenicity (Three-class) | Danger | 0.4551 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4271 | LogS |
| Caco-2 Permeability | 0.6361 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.3722 | LD50, mol/kg |
| Fish Toxicity | 0.6234 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6466 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Postnatal development of bitter taste avoidance behavior in mice is associated with ACTIN-dependent localization of bitter taste receptors to the microvilli of taste cells. | Biochem Biophys Res Commun | 2018 Jan 22 | 29278699 |
| Digestion and absorption of an egg white ACE-inhibitory peptide in human intestinal Caco-2 cell monolayers. | Int J Food Sci Nutr | 2016 | 26883099 |
| The Cardiomyopathy Lamin A/C D192G Mutation Disrupts Whole-Cell Biomechanics in Cardiomyocytes as Measured by Atomic Force Microscopy Loading-Unloading Curve Analysis. | Sci Rep | 2015 Sep 1 | 26323789 |
| Interaction of different Shiga toxin-producing Escherichia coli serotypes with Caco-2 cells. | Foodborne Pathog Dis | 2014 Nov | 25184783 |
| The anti-actin drugs latrunculin and cytochalasin affect the maturation of spruce somatic embryos in different ways. | Plant Sci | 2014 May | 24656339 |
| Shiga toxin production and translocation during microaerobic human colonic infection with Shiga toxin-producing E. coli O157:H7 and O104:H4. | Cell Microbiol | 2014 Aug | 24612002 |
| [Relation analysis between intracellular distribution of nanomateriarls, ROS generation and DNA damage]. | Yakugaku Zasshi | 2012 | 22382833 |
| The Nf-actin gene is an important factor for food-cup formation and cytotoxicity of pathogenic Naegleria fowleri. | Parasitol Res | 2010 Mar | 20143092 |
| A new model for hemoglobin ingestion and transport by the human malaria parasite Plasmodium falciparum. | J Cell Sci | 2008 Jun 1 | 18477610 |
| Actin is required for endocytic trafficking in the malaria parasite Plasmodium falciparum. | Cell Microbiol | 2008 Feb | 17944961 |
| Cellular differentiation in moss protonemata: a morphological and experimental study. | Ann Bot | 2008 Aug | 18508779 |
| Fine particles that adsorb lipopolysaccharide via bridging calcium cations may mimic bacterial pathogenicity towards cells. | Exp Biol Med (Maywood) | 2007 Jan | 17202591 |
| Adhesion and ingestion activities of fish phagocytes induced by bacterium Aeromonas salmonicida can be distinguished and directly measured from highly diluted whole blood of fish. | Dev Comp Immunol | 2005 | 15752549 |
| Downregulation of the growth hormone-induced Janus kinase 2/signal transducer and activator of transcription 5 signaling pathway requires an intact actin cytoskeleton. | Exp Cell Res | 2004 Mar 10 | 14980520 |
| A role for the cytoskeleton in prolactin-dependent mammary epithelial cell differentiation. | J Cell Sci | 2004 Jan 15 | 14676278 |
| Campylobacter fetus adheres to and enters INT 407 cells. | Can J Microbiol | 2002 Nov | 12556127 |
| MYO1, a novel, unconventional myosin gene affects endocytosis and macronuclear elongation in Tetrahymena thermophila. | J Eukaryot Microbiol | 2000 Nov-Dec | 11128708 |
| The actin cytoskeleton may control the polar distribution of an auxin transport protein. | Gravit Space Biol Bull | 2000 Jun | 11543284 |
| Perlecan heparan sulfate proteoglycan: a novel receptor that mediates a distinct pathway for ligand catabolism. | J Biol Chem | 2000 Aug 18 | 10818109 |
| Defective internalization and sustained activation of truncated granulocyte colony-stimulating factor receptor found in severe congenital neutropenia/acute myeloid leukemia. | Blood | 1999 Jan 15 | 9885206 |
Targets
- 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:
- 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 ]
- 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:
- 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 ]