(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: 133759
• 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)/b14-8-,16-15-/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• InChIKey: GBOGMAARMMDZGR-WIPIJLBNSA-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: Phomin; Cytochalasin B from Drechslera dematioidea; 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: 162228036; 24892890
• PubChem CID: 24870911

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: DMSO: soluble10 mg/mL
• Apperance: white powder

Safety Information

• RTECS: RO0205000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 63-26/27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H361
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• 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
• RID/ADR: UN 1544 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - C6762

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
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.