(4S)-4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-4-[(2S,3S)-2-(4-methoxy-4-oxobutanamido)-3-methylpentanamido]butanoic acid

• ChemBase ID: 106320
• Molecular Formular: C34H45F3N8O11
• Molecular Mass: 798.7633096
• Monoisotopic Mass: 798.31598896
• SMILES: CC[C@H](C)[C@H](NC(=O)CCC(=O)OC)C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)CCC(=O)O)[C@H](CC)C
• InChI: InChI=1S/C34H45F3N8O11/c1-4-17(2)29(45-24(46)10-12-27(50)55-3)32(54)44-22(9-11-26(48)49)30(52)41-16-25(47)43-21(6-5-13-40-33(38)39)31(53)42-18-7-8-19-20(34(35,36)37)15-28(51)56-23(19)14-18/h7-8,14-15,17,21-22,29H,4-6,9-13,16H2,1-3H3,(H,41,52)(H,42,53)(H,43,47)(H,44,54)(H,45,46)(H,48,49)(H4,38,39,40)/t17-,21-,22-,29-/m0/s1
• InChIKey: FQKBCPCULNZBOC-XKVCEYFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-4-[(2S,3S)-2-(4-methoxy-4-oxobutanamido)-3-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-[({[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-4-[(2S,3S)-2-(4-methoxy-4-oxobutanamido)-3-methylpentanamido]butanoic acid
• Synonyms: MeOSuc-Ile-Glu-Gly-Arg-AFC; MeOSuc-IEGR-AFC; MeOSuc-Ile-Glu-Gly-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105947
• PubChem CID: 25108540

CALCULATED PROPERTIES

• Acid pKa: -1.0301536
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -2.641245
• LogD (pH = 7.4): -2.6355634
• Log P: -2.635642
• Molar Refractivity: 199.797 cm^3
• Polarizability: 71.806694 Å^3
• Polar Surface Area: 297.3 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC067

A fluorogenic substrate for Factor Xa.

REFERENCES

• Kato, M. et al., Throm. Res., 50:77 (1998).