2-{[1-(2-{[1-(2-amino-3-methylbutanoyl)pyrrolidin-2-yl]formamido}-3-carboxypropanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

• ChemBase ID: 153545
• Molecular Formular: C25H42N8O8
• Molecular Mass: 582.64978
• Monoisotopic Mass: 582.31256034
• SMILES: CC(C)C(C(=O)N1CCCC1C(=O)NC(CC(=O)O)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)O)N
• Canonical SMILES: OC(=O)CC(C(=O)N1CCCC1C(=O)NC(C(=O)O)CCCNC(=N)N)NC(=O)C1CCCN1C(=O)C(C(C)C)N
• InChI: InChI=1S/C25H42N8O8/c1-13(2)19(26)23(39)33-11-5-8-17(33)21(37)31-15(12-18(34)35)22(38)32-10-4-7-16(32)20(36)30-14(24(40)41)6-3-9-29-25(27)28/h13-17,19H,3-12,26H2,1-2H3,(H,30,36)(H,31,37)(H,34,35)(H,40,41)(H4,27,28,29)
• InChIKey: KONFXBWESLMOCK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(2-{[1-(2-amino-3-methylbutanoyl)pyrrolidin-2-yl]formamido}-3-carboxypropanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: 2-{[1-(2-{[1-(2-amino-3-methylbutanoyl)pyrrolidin-2-yl]formamido}-3-carboxypropanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid
• Synonyms: Enterostatin (pig, rat); Val-Pro-Asp-Pro-Arg

Database IDs

• CAS Number: 117137-85-6
• PubChem SID: 162247684
• PubChem CID: 9959997

CALCULATED PROPERTIES

• Acid pKa: 3.2388828
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -6.7569003
• LogD (pH = 7.4): -6.8075414
• Log P: -6.7531323
• Molar Refractivity: 153.5219 cm^3
• Polarizability: 55.996872 Å^3
• Polar Surface Area: 261.34 Å^2
• Rotatable Bonds: 14
• 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): C25H42N8O8

DETAILS

Sigma Aldrich - V0256

Biochem/physiol Actions
An appetite suppressant in rats