4-{2-[2-(2-aminoacetamido)-3-carboxypropanamido]-3-phenylpropanamido}-4-{[1-({1-[2-({1-[(1-{[1-({1-[(3-carbamoyl-1-carboxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carboxypropyl)carbamoyl]-3-carboxypropyl}carbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl}carbamoyl)-3-carboxypropyl]carbamoyl}butanoic acid

• ChemBase ID: 153347
• Molecular Formular: C66H93N13O25
• Molecular Mass: 1468.51672
• Monoisotopic Mass: 1467.64055554
• SMILES: CCC(C)C(C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(Cc1ccc(cc1)O)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(Cc1ccccc1)NC(=O)C(CC(=O)O)NC(=O)CN
• Canonical SMILES: NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CCC(=O)N)CC(C)C)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)C(CC)C)CCC(=O)O)CCC(=O)O)Cc1ccccc1)CC(=O)O
• InChI: InChI=1S/C66H93N13O25/c1-5-34(4)55(78-59(96)41(21-26-53(89)90)71-56(93)38(18-23-50(83)84)72-61(98)44(29-35-10-7-6-8-11-35)77-63(100)46(31-54(91)92)69-49(82)32-67)65(102)79-27-9-12-47(79)64(101)73-40(20-25-52(87)88)57(94)70-39(19-24-51(85)86)58(95)76-45(30-36-13-15-37(80)16-14-36)62(99)75-43(28-33(2)3)60(97)74-42(66(103)104)17-22-48(68)81/h6-8,10-11,13-16,33-34,38-47,55,80H,5,9,12,17-32,67H2,1-4H3,(H2,68,81)(H,69,82)(H,70,94)(H,71,93)(H,72,98)(H,73,101)(H,74,97)(H,75,99)(H,76,95)(H,77,100)(H,78,96)(H,83,84)(H,85,86)(H,87,88)(H,89,90)(H,91,92)(H,103,104)
• InChIKey: ZNEKMMIWGPUTGR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[2-(2-aminoacetamido)-3-carboxypropanamido]-3-phenylpropanamido}-4-{[1-({1-[2-({1-[(1-{[1-({1-[(3-carbamoyl-1-carboxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carboxypropyl)carbamoyl]-3-carboxypropyl}carbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl}carbamoyl)-3-carboxypropyl]carbamoyl}butanoic acid
• IUPAC Traditional name: 4-{2-[2-(2-aminoacetamido)-3-carboxypropanamido]-3-phenylpropanamido}-4-{[1-({1-[2-({1-[(1-{[1-({1-[(3-carbamoyl-1-carboxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carboxypropyl)carbamoyl]-3-carboxypropyl}carbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl}carbamoyl)-3-carboxypropyl]carbamoyl}butanoic acid
• Synonyms: Hirudin Fragment 54-65 non-sulfated

Database IDs

• CAS Number: 113274-56-9
• MDL Number: MFCD00076563
• PubChem SID: 24895764; 162247486
• PubChem CID: 16132569

CALCULATED PROPERTIES

• Acid pKa: 2.9193225
• H Acceptors: 26
• H Donor: 19
• LogD (pH = 5.5): -14.8873415
• LogD (pH = 7.4): -23.081856
• Log P: -6.995339
• Molar Refractivity: 354.2626 cm^3
• Polarizability: 139.15338 Å^3
• Polar Surface Area: 624.45 Å^2
• Rotatable Bonds: 47
• 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): C66H93N13O25

DETAILS

Sigma Aldrich - H6769

Amino Acid Sequence
Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-Gln
Biochem/physiol Actions
Hirudin fragment that binds to the regulatory exosite I (proexosite I) on prothrombin with lower affinity than the sulfated peptide. It inhibits the activation of prothrombin by factor Xa in the presence of factor Va.