(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

• ChemBase ID: 126841
• Molecular Formular: C30H37NO6
• Molecular Mass: 507.61788
• Monoisotopic Mass: 507.26208791
• SMILES: C[C@@H]1CC=C[C@@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](C=C[C@@](C1=O)(C)O)OC(=O)C)C(=O)N[C@H]3Cc1ccccc1)C)O
• Canonical SMILES: CC(=O)O[C@@H]1C=C[C@@](C)(O)C(=O)[C@@H](CC=C[C@H]2[C@]31C(=O)N[C@H]([C@@H]3[C@H](C)C(=C)[C@H]2O)Cc1ccccc1)C
• 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)/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1
• InChIKey: SDZRWUKZFQQKKV-DIPXFXJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
• IUPAC Traditional name: cytochalasin D
• Synonyms: Zygosporin A; Cytohalasin D; Lygosporin A; Cytochalasin D; Cytochalasin D; 松胞菌素 D; 细胞松弛素 D

Database IDs

• CAS Number: 22144-77-0
• EC Number: 244-804-1
• MDL Number: MFCD00077706
• Beilstein Number: 1632828
• PubChem SID: 162221168
• PubChem CID: 5458428; 71308181
• Chemspider ID: 16736231
• Wikipedia Title: Cytochalasin_D

CALCULATED PROPERTIES

• Acid pKa: 12.848232
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.1152396
• LogD (pH = 7.4): 3.1152387
• Log P: 3.1152403
• Molar Refractivity: 141.5228 cm^3
• Polarizability: 54.907993 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 188.6 °F; 87 °C

Safety Information

• RTECS: GZ4850000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 2; 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 63-25
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H361
• GHS Precautionary statements: P264-P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1544 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Concentration: 5 mg/mL in DMSO
• Biological Source: from Zygosporium mansonii
• Sterility: 0.2 μm filtered
• Quality Level: PREMIUM
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C30H37NO6

DETAILS

Sigma Aldrich - C2618

Biochem/physiol Actions
Potent inhibitor of actin polymerization; disrupts actin microfilaments; activates the p53-dependent pathways; inhibits smooth muscle contraction; inhibits insulin-stimulated glucose transport.
Cell permeable fungal toxin; potent inhibitor of actin polymerization. Disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. Inhibits smooth muscle contraction. Inhibits insulin-stimulated, but not basal, transport of glucose.
Cytochalasin B is a cell permeable fungal toxin and potent inhibitor of actin polymerization. It disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. It inhibits smooth muscle contraction and insulin-stimulated, but not basal, transport of glucose.
Application
Cytochalasin B is used to inhibit sugar transport in fibroblasts 1, decrease cytoskeletal actin and myosin in rabbit neutrophils 2, and to stimulate B lymphocytes 3. It is a potent inhibitor of actin polymerization, disrupts actin microfilaments, activates the p53-dependent pathways, inhibits smooth muscle contraction, and inhibits insulin-stimulated glucose transport.

Sigma Aldrich - 859958

Biochem/physiol Actions
Potent inhibitor of actin polymerization; disrupts actin microfilaments; activates the p53-dependent pathways; inhibits smooth muscle contraction; inhibits insulin-stimulated glucose transport.

Sigma Aldrich - 30385

Biochem/physiol Actions
Potent inhibitor of actin polymerization; disrupts actin microfilaments; activates the p53-dependent pathways; inhibits smooth muscle contraction; inhibits insulin-stimulated glucose transport.