7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
Basic information
- CAS
14930-96-2- Standard SMILES
C=C1C(C)C2C(Cc3ccccc3)NC(=O)C23OC(=O)/C=C\C(O)CCCC(C)C/C=C\C3C1O- InChIKey
GBOGMAARMMDZGR-NBOXQWGESA-N- Molecular formula
- C29H37NO5
- Average molar mass
- 479.6 g/mol
- Monoisotopic mass
- 479.26717328
Names & identifiers
- Preferred name
- 7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
- IUPAC
- (4Z,12Z)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
- English name
- CYTOCHALASIN B
- Molecular formula
- C29H37NO5
- Molecular weight
- 479.61
Names & synonyms
7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-triene-1,23-dioneRefChem:544687cytochalasinPHOMIN(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-OXACYCLOTETRADE[2,3-D]ISOINDOLE-2,18(5H)-DIONE-23-oneCYTOCHALACINBCYTOCHALICINBCYTOCHALASIN BCYTOCHALASIN B(RG)Cytochalasin B (Phomin)
Show more names
CYTOCHALASIN B USP/EP/BP
Database identifiers
- CAS
14930-96-2- PubChem CID
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 95.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 859
Physicochemical properties
- Melting point
- 218 · 218-223 °C
- Boiling point
- 577.96 °C · 577.96°C (rough estimate)
- Density
- 1.149 · 1.1490 (rough estimate)
- refractive index
- 1.629 · 1.6290 (estimate)
- Flash point
- 85 ℃ · 85℃
- storage temp.
- -20 °C · -20°C
- solubility
- 20 mg/mL · ethanol: 20 mg/mL
- form
- powder
- pka
- 13.6 · 13.60±0.70(Predicted)
- color
- white
- Merck
- 13 · 13,2819
- BRN
- 1096207 · 1096207
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- InChIKey
- UXVDBQLLXVKPRS-UZBFCAAUSA-N
- SMILES
- C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@@H](\C=C\C1)[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](Cc4ccccc4)NC3=O
- LogP
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300+H310+H330 (38.7%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 75 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- F
- 10
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- RO0205000
- ridadr
- UN 1544 6.1/PG 2
- hs_code
- 29349990
- Toxicity
- LD50 intraperitoneal in mouse: 30mg/kg
- risk_code
- 26/27/28-63-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T+,T
- safety_code
- 28-36/37-45
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Chemistry & industry
Applications
DescriptionCytochalasin B (14930-96-2) is a cell permeable fungal toxin which binds to the barbed end of actin, inhibiting its polymerization.1 Inhibits cell division, migration and glucose transport.2 Causes cell cycle arrest at G2/M and induces apoptosis in HCT-116 colorectal carcinoma cells.3 Cytochalasin B-induced membrane vesicles (CIMVs) retain cell surface receptors of the parent cells and retain fusion specificity with target cells.4 CIMVs are a promising new vector system for drug and biomolecule delivery due to their natural origin and participation in intercellular communication.5
UsesCytochalasin B is one of the most extensively studied members of a family of potent mycotoxins produced by several species of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, giving rise to pronounced morphogenic activity in animals and plants. Like most cytochalsins, cytochalasin B exhibits potent inhibition of actin filament function leading to cell death by apoptosis, and displays a broad range of resultant cellular actions. Despite the common mode of action, there is evidence that individual members of this class display diverse selectivity. However, lack of comparative co-metabolite analysis has restricted a more complete understanding of their individual selectivity.
UsesA cell-permeable fungal toxin used in actin polymerization studies and cytological
UsesAs tools in cytological research and in characterization of polymerization properties of actin, q.v.
General DescriptionCytochalasin B is a cell-permeable fungal toxin / mycotoxin that binds to the ′barbed′ end of actin / actin filaments. This binding leads to:Disruption of actin filaments and of interaction of actin filaments in solutionInhibition of actin polymerizationInhibition of subunit association and dissociationCytochalasin B is widely used in studies of glucose transporters (GLUT). Cytochalasin B is also used as an integral part of various in vitro micronucleus assay protocols.
Upstream & downstream products
Downstream products
Related reactions
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Compound notes
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