Cytochalasin H
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Basic Info
| Common Name | Cytochalasin H(F04930) |
| 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 H is has been isolated from the fungus Phomopsis paspali. It also regulates plant growth and has shown CNS activity. (A2910, A2911, L1913, L1916) |
| FRCD ID | F04930 |
| CAS Number | 53760-19-3 |
| PubChem CID | 5351303 |
| Formula | C30H39NO5 |
| IUPAC Name | None |
| InChI Key | NAEWXXDGBKTIMN-BBXOWAOSSA-N |
| InChI | InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+ |
| Canonical SMILES | CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1)(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)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O |
| Synonyms |
NSC305222
CYTOCHALASIN H
Kodocytochalasin 1
MLS002701799
53760-19-3
CHEMBL2003636
NSC-305222
[11]Cytochalasa-6(12),19-trien-1-one, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-
1H-Cycloundec[d]isoindol-1-one,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro- 6,12-dihydroxy-4,10,12-trimethyl-5-methylene- 3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-
|
| 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 - Monocyclic benzene moiety - Pyrrolidone - 2-pyrrolidone - Benzenoid - Tertiary alcohol - Pyrrolidine - Cyclic alcohol - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Lactam - Carboxylic acid ester - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Azacycle - Carboxylic acid derivative - Alcohol - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Carbonyl group - 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 | 493.644 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 920 |
| Monoisotopic Mass | 493.283 |
| Exact Mass | 493.283 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 36 |
| 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+ | 0.7045 |
| Human Intestinal Absorption | HIA+ | 0.9009 |
| Caco-2 Permeability | Caco2- | 0.6276 |
| P-glycoprotein Substrate | Substrate | 0.7098 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8631 |
| Non-inhibitor | 0.5237 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8602 |
| Distribution | ||
| Subcellular localization | Plasma membrane | 0.7524 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8208 |
| CYP450 2D6 Substrate | Non-substrate | 0.8492 |
| CYP450 3A4 Substrate | Substrate | 0.7396 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8956 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7004 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9426 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6887 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7573 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6651 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9836 |
| Non-inhibitor | 0.8993 | |
| AMES Toxicity | Non AMES toxic | 0.7392 |
| Carcinogens | Non-carcinogens | 0.8976 |
| Fish Toxicity | High FHMT | 0.9813 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9876 |
| Honey Bee Toxicity | High HBT | 0.5864 |
| Biodegradation | Not ready biodegradable | 0.9944 |
| Acute Oral Toxicity | I | 0.3318 |
| Carcinogenicity (Three-class) | Danger | 0.4410 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5845 | LogS |
| Caco-2 Permeability | 0.6111 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.4878 | LD50, mol/kg |
| Fish Toxicity | 0.4998 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6357 | pIGC50, ug/L |
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:
- 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 ]
- 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 ]