2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride

• ChemBase ID: 133234
• Molecular Formular: C27H46Cl2N10O6
• Molecular Mass: 677.62354
• Monoisotopic Mass: 676.2978846
• SMILES: CC(C)[C@@H](C(=O)NC(CCCNC(=N)N)C=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)NC(Cc1ccccc1)C(=O)O.Cl.Cl
• Canonical SMILES: O=CC(NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)NC(C(=O)O)Cc1ccccc1)CCCNC(=N)N)CCCNC(=N)N.Cl.Cl
• InChI: InChI=1S/C27H44N10O6.2ClH/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17;;/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43);2*1H/t18?,19-,20?,21-;;/m0../s1
• InChIKey: YAHXZYICKJUJEO-BXLPLHKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride
• IUPAC Traditional name: 2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride
• Synonyms: N-(Nα-Carbonyl-Arg-Val-Arg-al)-Phe; Antipain dihydrochloride from microbial source

Database IDs

• CAS Number: 37682-72-7
• MDL Number: MFCD00135957
• PubChem SID: 24891067; 162227511
• PubChem CID: 16218941

CALCULATED PROPERTIES

• Acid pKa: 3.433761
• H Acceptors: 12
• H Donor: 11
• LogD (pH = 5.5): -5.394688
• LogD (pH = 7.4): -5.3856344
• Log P: -3.4464593
• Molar Refractivity: 178.2286 cm^3
• Polarizability: 60.508217 Å^3
• Polar Surface Area: 277.5 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1-butanol: soluble; 1-propanol: soluble; DMSO: soluble; ethanol: soluble; H2O: soluble50 mg/mL; methanol: soluble

Safety Information

• RTECS: YV9350800
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - A6191

Application
Concentrations for 50% inhibition (μg/ml): papain, 0.16trypsin, 0.26cathepsin A, 1.19cathepsin B, 0.59cathepsin D, 125plasmin, >93chymotrypsin and pepsin, >250It also has been reported to inhibit calpain I, (porcine) with Ki = 1.4 μM
Preparation Note
Solubility testing at 50 mg/ml in water yields a clear to slightly hazy yellow solution. It is reportedly soluble in methanol, water, and DMSO; less soluble in ethanol, butanol, and propanol; insoluble in benzene, hexane, and chloroform.8 A stock solution in water or buffer is stable for about a month at -20 °C.Dilute solutions should be stored on ice and kept for only a day because of the terminal aldehyde, which is subject to oxidation and racemization.
Stock solutions in water or buffer stable for 1 week at 4 °C, 1 month at -20 °C.
Biochem/physiol Actions
Reversible inhibitor of serine/cysteine proteases and some trypsin-like serine proteases. Its action resembles leupeptin; however, its plasmin inhibition is less and its cathepsin A inhibition is more than that observed with leupeptin. Chronic administration of antipain can reduce the frequency of chemically induced transformation in BALB/c-/3T3 cells.1