(2R,4R)-1-{5-carbamimidamido-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl}-4-methylpiperidine-2-carboxylic acid

• ChemBase ID: 160797
• Molecular Formular: C23H36N6O5S
• Molecular Mass: 508.63414
• Monoisotopic Mass: 508.24678928
• SMILES: N(C(CCCNC(=N)N)C(=O)N1[C@H](C[C@@H](CC1)C)C(=O)O)S(=O)(=O)c1cccc2c1NC[C@@H](C2)C
• Canonical SMILES: NC(=N)NCCCC(C(=O)N1CC[C@H](C[C@@H]1C(=O)O)C)NS(=O)(=O)c1cccc2c1NC[C@@H](C2)C
• InChI: InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15-,17?,18-/m1/s1
• InChIKey: KXNPVXPOPUZYGB-IXOSTLECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-1-{5-carbamimidamido-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl}-4-methylpiperidine-2-carboxylic acid
• IUPAC Traditional name: (2R,4R)-1-{5-carbamimidamido-2-[(3R)-3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido]pentanoyl}-4-methylpiperidine-2-carboxylic acid
• Synonyms: (2R,4R)-1-[(2S)-5-[(Aminoiminomethyl)amino]-1-oxo-2-[[[(3R)-1,2,3,4-tetrahydro-3-methyl-8-quinolinyl]sulfonyl]amino]pentyl]-4-methyl-2-piperidinecarboxylic Acid; 21R-Argatroban

Database IDs

• CAS Number: 121785-71-5
• PubChem SID: 162254932
• PubChem CID: 60071075

CALCULATED PROPERTIES

• Acid pKa: 3.137495
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.9171229
• LogD (pH = 7.4): -0.9158829
• Log P: -0.91570914
• Molar Refractivity: 143.829 cm^3
• Polarizability: 51.34015 Å^3
• Polar Surface Area: 177.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A768990

The 21R-stereoisomer of Argatroban. Synthetic thrombin inhibitor. Antithrombotic.

REFERENCES

• Abiko, Y., et al.: Thromb. Res., 24, 285 (1981)
• Kikumoto, R., et al.: Biochemistry, 23, 85 (1981)