2-[11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid

• ChemBase ID: 168141
• Molecular Formular: C35H49N11O9S2
• Molecular Mass: 831.96186
• Monoisotopic Mass: 831.3156142
• SMILES: C1(=O)C(NC(=O)CCSSCC(NC(=O)C2N(C(=O)C(NC(=O)C(NC(=O)CN1)CC(=O)O)Cc1c3c([nH]c1)cccc3)CCC2)C(=O)N)CCCCNC(=N)N
• Canonical SMILES: OC(=O)CC1NC(=O)CNC(=O)C(CCCCNC(=N)N)NC(=O)CCSSCC(NC(=O)C2N(C(=O)C(NC1=O)Cc1c[nH]c3c1cccc3)CCC2)C(=O)N
• InChI: InChI=1S/C35H49N11O9S2/c36-30(51)25-18-57-56-13-10-27(47)42-22(8-3-4-11-39-35(37)38)31(52)41-17-28(48)43-23(15-29(49)50)32(53)44-24(14-19-16-40-21-7-2-1-6-20(19)21)34(55)46-12-5-9-26(46)33(54)45-25/h1-2,6-7,16,22-26,40H,3-5,8-15,17-18H2,(H2,36,51)(H,41,52)(H,42,47)(H,43,48)(H,44,53)(H,45,54)(H,49,50)(H4,37,38,39)
• InChIKey: CZKPOZZJODAYPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
• IUPAC Traditional name: [11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-hexadecahydro-2H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
• Synonyms: N6-(Aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-.alpha.-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide Cyclic (16)-Disulfide; Integrelin; Integrilin; Intrifiban; Eptifibatide; 2-[11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid

Database IDs

• CAS Number: 188627-80-7
• MDL Number: MFCD22628549
• PubChem SID: 162262273
• PubChem CID: 123610

CALCULATED PROPERTIES

• Acid pKa: 3.6680408
• H Acceptors: 12
• H Donor: 11
• LogD (pH = 5.5): -5.068173
• LogD (pH = 7.4): -5.0630093
• Log P: -5.063064
• Molar Refractivity: 219.8379 cm^3
• Polarizability: 82.15443 Å^3
• Polar Surface Area: 323.89 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.862

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - E592000

A Arginin-glycin-aspartat-mimetic, reversibly binds to platelets to reduce the risk of cardiac ischemic events.

REFERENCES

• Pathak, A., et al.: Cardiovas. Diabetol., 7 (2008)
• Hantgan, R., et al.: Biochem., 48, 8355 (2008)
• Giugliano, R., et al.: New Eng. J. Med., 360, 2176 (2008)