3-hydroxy-4-[2-(3-hydroxy-6-methyl-4-{3-methyl-2-[3-methyl-2-(2-methylpropanamido)butanamido]butanamido}heptanamido)propanamido]-6-methylheptanoic acid

• ChemBase ID: 153310
• Molecular Formular: C33H61N5O9
• Molecular Mass: 671.86554
• Monoisotopic Mass: 671.44692856
• SMILES: CC(C)CC(C(CC(=O)O)O)NC(=O)C(C)NC(=O)CC(C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C(C(C)C)NC(=O)C(C)C)O
• Canonical SMILES: CC(CC(C(CC(=O)NC(C(=O)NC(C(CC(=O)O)O)CC(C)C)C)O)NC(=O)C(C(C)C)NC(=O)C(C(C)C)NC(=O)C(C)C)C
• InChI: InChI=1S/C33H61N5O9/c1-16(2)12-22(36-32(46)28(18(5)6)38-33(47)29(19(7)8)37-30(44)20(9)10)24(39)14-26(41)34-21(11)31(45)35-23(13-17(3)4)25(40)15-27(42)43/h16-25,28-29,39-40H,12-15H2,1-11H3,(H,34,41)(H,35,45)(H,36,46)(H,37,44)(H,38,47)(H,42,43)
• InChIKey: QNPQJKICJQEMBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxy-4-[2-(3-hydroxy-6-methyl-4-{3-methyl-2-[3-methyl-2-(2-methylpropanamido)butanamido]butanamido}heptanamido)propanamido]-6-methylheptanoic acid
• IUPAC Traditional name: 3-hydroxy-4-[2-(3-hydroxy-6-methyl-4-{3-methyl-2-[3-methyl-2-(2-methylpropanamido)butanamido]butanamido}heptanamido)propanamido]-6-methylheptanoic acid
• Synonyms: Isobutyryl-Val-Val-Sta-Ala-Sta (Sta = statine = (3S,4S)-4-Amino-3-hydroxy-6-methylheptanoic acid); Pepsinostreptin

Database IDs

• CAS Number: 51724-57-3
• MDL Number: MFCD00214075
• PubChem SID: 162247449
• PubChem CID: 4667579

CALCULATED PROPERTIES

• Acid pKa: 4.3156843
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): 0.31989175
• LogD (pH = 7.4): -1.421755
• Log P: 1.5297693
• Molar Refractivity: 174.8441 cm^3
• Polarizability: 69.432205 Å^3
• Polar Surface Area: 223.26 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C33H61N5O9

DETAILS

Sigma Aldrich - P7424

Biochem/physiol Actions
Forms a 1:1 complex with pepsin and inhibits its activity.