(1S,5Z,7R,9S,11Z,13S,14S,16R,17S,18S,19S)-19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-5,11-diene-3,8,21-trione

• ChemBase ID: 134158
• Molecular Formular: C28H33NO7
• Molecular Mass: 495.56412
• Monoisotopic Mass: 495.2257024
• SMILES: C[C@H]1C/C=C\[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]3[C@]2(C(=O)N[C@H]3Cc2ccccc2)OC(=O)O/C=C\[C@@](C1=O)(C)O)C)C
• Canonical SMILES: O=C1O/C=C\[C@@](C)(O)C(=O)[C@H](C/C=C\[C@@H]2[C@]3(O1)C(=O)N[C@H]([C@@H]3[C@H](C)[C@@]1([C@H]2O1)C)Cc1ccccc1)C
• InChI: InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8-,14-13-/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1
• InChIKey: LAJXCUNOQSHRJO-SENKRXSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5Z,7R,9S,11Z,13S,14S,16R,17S,18S,19S)-19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^1,^1^8.0^1^4,^1^6]henicosa-5,11-diene-3,8,21-trione
• IUPAC Traditional name: (1S,5Z,7R,9S,11Z,13S,14S,16R,17S,18S,19S)-19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^1,^1^8.0^1^4,^1^6]henicosa-5,11-diene-3,8,21-trione
• Synonyms: Cytochalasin E from Aspergillus clavatus

Database IDs

• CAS Number: 36011-19-5
• EC Number: 252-835-7
• MDL Number: MFCD00005178
• Beilstein Number: 1096975
• PubChem SID: 24892467; 162228435
• PubChem CID: 71308766

CALCULATED PROPERTIES

• Acid pKa: 12.537551
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.7027762
• LogD (pH = 7.4): 3.7027733
• Log P: 3.7027762
• Molar Refractivity: 131.3269 cm^3
• Polarizability: 51.537853 Å^3
• Polar Surface Area: 114.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: HA5360000
• 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

DETAILS

Sigma Aldrich - C2149

Biochem/physiol Actions
Cytochalasin E is a cell-permeable fungal toxin that inhibits actin polymerization stimulated by F-actin. Cytochalasin E does not inhibit glucose transport.