(2R,4R)-4-methyl-1-[(2S)-2-(3-methylquinoline-8-sulfonamido)-5-(1-nitrocarbamimidamido)pentanoyl]piperidine-2-carboxylic acid

• ChemBase ID: 175528
• Molecular Formular: C23H31N7O7S
• Molecular Mass: 549.59994
• Monoisotopic Mass: 549.20056737
• SMILES: N([C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)N1[C@H](C[C@@H](CC1)C)C(=O)O)S(=O)(=O)c1cccc2c1ncc(c2)C
• Canonical SMILES: C[C@@H]1CCN([C@H](C1)C(=O)O)C(=O)[C@@H](NS(=O)(=O)c1cccc2c1ncc(c2)C)CCCNC(=N)N[N+](=O)[O-]
• InChI: InChI=1S/C23H31N7O7S/c1-14-8-10-29(18(12-14)22(32)33)21(31)17(6-4-9-25-23(24)27-30(34)35)28-38(36,37)19-7-3-5-16-11-15(2)13-26-20(16)19/h3,5,7,11,13-14,17-18,28H,4,6,8-10,12H2,1-2H3,(H,32,33)(H3,24,25,27)/t14-,17+,18-/m1/s1
• InChIKey: XBDLKMBSCAVLDV-FHLIZLRMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-4-methyl-1-[(2S)-2-(3-methylquinoline-8-sulfonamido)-5-(1-nitrocarbamimidamido)pentanoyl]piperidine-2-carboxylic acid
• IUPAC Traditional name: (2R,4R)-4-methyl-1-[(2S)-2-(3-methylquinoline-8-sulfonamido)-5-(1-nitrocarbamimidamido)pentanoyl]piperidine-2-carboxylic acid
• Synonyms: (2R,4R)-1-[(2S)-5-[[Imino(nitroamino)methyl]amino]-2-[[(3-methyl-8-quinolinyl)sulfonyl]amino]-1-oxopentyl]-4-methyl-2-piperidinecarboxylic Acid; [2R-[1(S*),2α,4β]]-1-[5-[[Imino(nitroamino)methyl]amino]-2-[[(3-methyl-8-quinolinyl)sulfonyl]amino]-1-oxopentyl]-4-methyl-2-piperidinecarboxylic Acid; N-Nitro-1,2,3,4-tetradehydro Argatroban

Database IDs

• CAS Number: 74874-10-5
• PubChem SID: 164231438
• PubChem CID: 57514094

CALCULATED PROPERTIES

• Acid pKa: 3.514299
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.2731762
• LogD (pH = 7.4): -1.6311978
• Log P: -0.12146716
• Molar Refractivity: 147.2018 cm^3
• Polarizability: 53.888493 Å^3
• Polar Surface Area: 210.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 201-204°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - N565115

N-Nitro-1,2,3,4-tetradehydro Argatroban is an intermediate in the preparation of Argatroban (A769000).