(3S,6S,15aR)-9-(butan-2-yl)-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

• ChemBase ID: 154207
• Molecular Formular: C34H49N5O6
• Molecular Mass: 623.78276
• Monoisotopic Mass: 623.36828431
• SMILES: CCC(C)C1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1cn(c2c1cccc2)OC)CCCCCC(=O)CC
• Canonical SMILES: CCC(=O)CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)C(NC(=O)[C@@H](NC1=O)Cc1cn(c2c1cccc2)OC)C(CC)C
• InChI: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22?,26-,27-,29+,30?/m0/s1
• InChIKey: JWOGUUIOCYMBPV-PYAAAQPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,15aR)-9-(butan-2-yl)-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• IUPAC Traditional name: (3S,6S,15aR)-6-[(1-methoxyindol-3-yl)methyl]-3-(6-oxooctyl)-9-(sec-butyl)-decahydro-2H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• Synonyms: Cyclo[(2S)-2-amino-8-oxodecanoyl-1-methoxy-L-tryptophyl-L-isoleucyl-(2R)-2-piperidinexcarbonyl]; Apicidin

Database IDs

• CAS Number: 183506-66-3
• MDL Number: MFCD03452661
• PubChem SID: 162248346
• PubChem CID: 57568978

CALCULATED PROPERTIES

• Acid pKa: 10.834099
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.374681
• LogD (pH = 7.4): 3.3745413
• Log P: 3.374683
• Molar Refractivity: 171.2108 cm^3
• Polarizability: 67.55282 Å^3
• Polar Surface Area: 138.84 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: ~1 mg/mL; DMSO: ~1 mg/mL
• Apperance: solid

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
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-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
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Biological Source: from microbial
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C34H49N5O6

DETAILS

Sigma Aldrich - A8851

Biochem/physiol Actions
Potent (nM) cell permeable inhibitor of histone deacetylase. Also, exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa cells accompanied by cell arrest at the G1 phase. In addition, it induces selective changes in the expression of p21 and gelsolin.