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

• ChemBase ID: 131192
• Molecular Formular: C28H37NO4
• Molecular Mass: 451.59768
• Monoisotopic Mass: 451.27225867
• 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)(C)O)O)C(=O)N[C@H]3Cc1ccccc1)C)O
• Canonical SMILES: C[C@H]1CC=C[C@H]2[C@H](O)C(=C)[C@H]([C@@H]3[C@@]2([C@@H](C=C[C@@](C1)(C)O)O)C(=O)N[C@H]3Cc1ccccc1)C
• InChI: InChI=1S/C28H37NO4/c1-17-9-8-12-21-25(31)19(3)18(2)24-22(15-20-10-6-5-7-11-20)29-26(32)28(21,24)23(30)13-14-27(4,33)16-17/h5-8,10-14,17-18,21-25,30-31,33H,3,9,15-16H2,1-2,4H3,(H,29,32)/b12-8-,14-13-/t17-,18+,21-,22-,23+,24-,25+,27+,28+/m0/s1
• InChIKey: UKQNIEMKORIOQM-MRWBMVALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one
• IUPAC Traditional name: (3S,4S,6S,6aR,10S,12S,15R,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-1-one
• Synonyms: Cytochalasin J from Phomopsis sp.

Database IDs

• CAS Number: 53760-20-6
• MDL Number: MFCD00077708
• PubChem SID: 162225470
• PubChem CID: 71308400

CALCULATED PROPERTIES

• Acid pKa: 13.708873
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.929523
• LogD (pH = 7.4): 2.9295235
• Log P: 2.9295237
• Molar Refractivity: 131.8062 cm^3
• Polarizability: 51.00005 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-40
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H351
• 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 2811 6.1/PG 2
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C1139

Biochem/physiol Actions
Cytochalasin reported to have CNS activity