(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-N-(4-methoxynaphthalen-2-yl)propanamide; acetic acid

• ChemBase ID: 131381
• Molecular Formular: C22H27N5O6
• Molecular Mass: 457.47968
• Monoisotopic Mass: 457.19613361
• SMILES: CC(=O)O.COc1cc(cc2c1cccc2)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]cn1)N
• Canonical SMILES: CC(=O)O.OC[C@@H](C(=O)Nc1cc(OC)c2c(c1)cccc2)NC(=O)[C@H](Cc1c[nH]cn1)N
• InChI: InChI=1S/C20H23N5O4.C2H4O2/c1-29-18-8-13(6-12-4-2-3-5-15(12)18)24-20(28)17(10-26)25-19(27)16(21)7-14-9-22-11-23-14;1-2(3)4/h2-6,8-9,11,16-17,26H,7,10,21H2,1H3,(H,22,23)(H,24,28)(H,25,27);1H3,(H,3,4)/t16-,17-;/m0./s1
• InChIKey: APZWSSHDMOSDHZ-QJHJCNPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-N-(4-methoxynaphthalen-2-yl)propanamide; acetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-N-(4-methoxynaphthalen-2-yl)propanamide; acetic acid
• Synonyms: His-Ser 4-methoxy-β-naphthylamide acetate salt

Database IDs

• CAS Number: 100929-87-1
• MDL Number: MFCD03788129
• PubChem SID: 162225659
• PubChem CID: 71308431

CALCULATED PROPERTIES

• Acid pKa: 11.760743
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.7504706
• LogD (pH = 7.4): -0.722333
• Log P: -0.32835314
• Molar Refractivity: 107.5251 cm^3
• Polarizability: 42.362053 Å^3
• Polar Surface Area: 142.36 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - H9758

Substrates
Substrate for dipeptidyl aminopeptidase I (cathepsin C).