2-{2-[2-(2-{2-[2-({1-[2-amino-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-(1H-imidazol-5-yl)propanamido}-4-methylpentanamido)-4-methylpentanamido]-3-methylbutanamido}-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 131526
• Molecular Formular: C52H72N12O10
• Molecular Mass: 1025.20248
• Monoisotopic Mass: 1024.54943656
• SMILES: CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(Cc1ccc(cc1)O)C(=O)O)NC(=O)C(Cc1cnc[nH]1)NC(=O)C(Cc1ccccc1)NC(=O)C1CCCN1C(=O)C(Cc1cnc[nH]1)N
• Canonical SMILES: CC(CC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccc(cc1)O)C(C)C)CC(C)C)NC(=O)C(NC(=O)C(NC(=O)C1CCCN1C(=O)C(Cc1[nH]cnc1)N)Cc1ccccc1)Cc1[nH]cnc1)C
• InChI: InChI=1S/C52H72N12O10/c1-29(2)19-38(45(66)59-39(20-30(3)4)48(69)63-44(31(5)6)50(71)62-42(52(73)74)22-33-14-16-36(65)17-15-33)58-47(68)41(24-35-26-55-28-57-35)60-46(67)40(21-32-11-8-7-9-12-32)61-49(70)43-13-10-18-64(43)51(72)37(53)23-34-25-54-27-56-34/h7-9,11-12,14-17,25-31,37-44,65H,10,13,18-24,53H2,1-6H3,(H,54,56)(H,55,57)(H,58,68)(H,59,66)(H,60,67)(H,61,70)(H,62,71)(H,63,69)(H,73,74)
• InChIKey: FDIFVHOZUBKVOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-{2-[2-({1-[2-amino-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-(1H-imidazol-5-yl)propanamido}-4-methylpentanamido)-4-methylpentanamido]-3-methylbutanamido}-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: 2-{2-[2-(2-{2-[2-({1-[2-amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-(3H-imidazol-4-yl)propanamido}-4-methylpentanamido)-4-methylpentanamido]-3-methylbutanamido}-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: [D-Leu6}-Octapeptide; His-Pro-Phe-His-Leu-D-Leu-Val-Tyr

Database IDs

• CAS Number: 50410-01-0
• MDL Number: MFCD00133401
• PubChem SID: 162225804
• PubChem CID: 5225093

CALCULATED PROPERTIES

• Acid pKa: 3.44869
• H Acceptors: 13
• H Donor: 11
• LogD (pH = 5.5): -2.230032
• LogD (pH = 7.4): -0.9236762
• Log P: -0.9874348
• Molar Refractivity: 271.9533 cm^3
• Polarizability: 105.85257 Å^3
• Polar Surface Area: 335.82 Å^2
• Rotatable Bonds: 27
• 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

• Compostion: Peptide content, ~65%

DETAILS

Sigma Aldrich - H5396

Biochem/physiol Actions
Potent inhibitor of renin at acidic pH. Can be linked to agarose and used to purify renin, which elutes at neutral pH.