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

• ChemBase ID: 155898
• Molecular Formular: C27H44N10O6
• Molecular Mass: 604.70166
• Monoisotopic Mass: 604.34452918
• SMILES: CC(C)[C@@H](C(=O)NC(CCCNC(=N)N)C=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)N[C@@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: O=CC(NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)N[C@H](C(=O)O)Cc1ccccc1)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C27H44N10O6/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)/t18?,19-,20-,21-/m0/s1
• InChIKey: SDNYTAYICBFYFH-KTYMLHDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid
• Synonyms: [(S)-1-Carboxy-2-phenylethyl]carbamoyl-L-arginyl-L-valyl-argininal; Antipain

Database IDs

• CAS Number: 37691-11-5
• EC Number: 253-631-0
• MDL Number: MFCD00135959
• Beilstein Number: 6837629
• PubChem SID: 24846788; 162250036
• PubChem CID: 16211183

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

Safety Information

• RTECS: YV9350700
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C27H44N10O6

DETAILS

Sigma Aldrich - 10791

Biochem/physiol Actions
Inhibits serine/cysteine proteases and some trypsin-like proteases. Compare activity to that of leupeptin. Used to evaluate the role of proteases in cell transformations. Used to help identify new proteases.
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 can reduce the frequency of chemically induced transformation in BALB/c-/3T3 cells.1
Other Notes
Protease inhibitor2
Unit Definition
1 U corresponds to the amount of inhibitor which reduces the trypsin activity by 1 BAEE-U. (1 BAEE-U is the amount of enzyme which increases the absorbance at 253 nm by 0.001 per minute at pH 7.6 and 25°C; BAEE, Fluka No. 12880, as substrate)