(5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

• ChemBase ID: 138656
• Molecular Formular: C29H37NO5
• Molecular Mass: 479.60778
• Monoisotopic Mass: 479.26717329
• SMILES: C[C@@H]1CCC[C@H](/C=C\C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)Cc1ccccc1)C)O)O
• Canonical 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@H]3[C@@H](NC2=O)Cc1ccccc1)C
• 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)/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• InChIKey: GBOGMAARMMDZGR-BKRFDJOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione
• IUPAC Traditional name: cytochalasin B
• Synonyms: Cytochalasin B from Helminthosporium dematioideum; Phomin; Cytochalasin B from Drechslera dematioidea; 细胞松弛素 B 来源于长蠕孢菌; 细胞松弛素 B 来源于Drechslera dematioidea

Database IDs

• CAS Number: 14930-96-2
• EC Number: 239-000-2
• MDL Number: MFCD00077704
• Beilstein Number: 1096207
• PubChem SID: 162232907; 24858145
• PubChem CID: 44634701

CALCULATED PROPERTIES

• Acid pKa: 13.110297
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.082357
• LogD (pH = 7.4): 4.082356
• Log P: 4.082357
• Molar Refractivity: 136.417 cm^3
• Polarizability: 52.98627 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble20 mg/mL, clear, colorless
• Flash Point: 185 °F; 85 °C

Safety Information

• RTECS: RO0205000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 1544; 3140
• German water hazard class: 2; 3
• Hazard Class: 6.1
• Packing Group: 2; 3
• Risk Statements: 23/24/25; 63-26/27/28
• Safety Statements: 28-36/37-45; 36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300 +H310 + H330-H361; H302-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P284-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, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1544 6.1/PG 2; UN 3140 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC)
• Concentration: 10 mg/mL in DMSO
• Sterility: 0.2 μm filtered
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C29H37NO5

DETAILS

Sigma Aldrich - C2743

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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.
Biochem/physiol Actions
One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin,4 and in studies on cytokinesis.5 Probe for the two hexose-transport systems in rat L6 myoblasts.6
Cell permeable fungal toxin that disrupts contractile microfilaments by inhibiting actin polymerization. This, in turn, induces DNA fragmentation, inhibits cell division, and disrupts many cell processes. Inhibits glucose transport.

Sigma Aldrich - 30380

Biochem/physiol Actions
One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin,1 and in studies on cytokinesis.2 Probe for the two hexose-transport systems in rat L6 myoblasts.3