(4S)-4-{[(1S)-1-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid

• ChemBase ID: 132739
• Molecular Formular: C19H30N4O10S
• Molecular Mass: 506.5273
• Monoisotopic Mass: 506.16826418
• SMILES: CC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C=O
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@@H](CC(=O)O)C=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CCC(=O)O)CO
• InChI: InChI=1S/C19H30N4O10S/c1-10(26)20-12(3-4-15(27)28)18(32)23-14(9-25)19(33)22-13(5-6-34-2)17(31)21-11(8-24)7-16(29)30/h8,11-14,25H,3-7,9H2,1-2H3,(H,20,26)(H,21,31)(H,22,33)(H,23,32)(H,27,28)(H,29,30)/t11-,12-,13-,14-/m0/s1
• InChIKey: TVTYMGFOGZRIHG-XUXIUFHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid
• Synonyms: Ac-ESMD-CHO; N-Acetyl-Glu-Ser-Met-Asp-al

Database IDs

• MDL Number: MFCD01318859
• PubChem SID: 162227016
• PubChem CID: 11398034

CALCULATED PROPERTIES

• Acid pKa: 3.649199
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -7.0211825
• LogD (pH = 7.4): -10.282292
• Log P: -3.918482
• Molar Refractivity: 116.3661 cm^3
• Polarizability: 45.787724 Å^3
• Polar Surface Area: 228.3 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - A1341

Biochem/physiol Actions
Blocks the formation of the active p17 subunit of caspase 3 from its precursor and induces accumulation of the p20 precursor peptide.