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

• ChemBase ID: 106421
• Molecular Formular: C34H48N8O11
• Molecular Mass: 744.79192
• Monoisotopic Mass: 744.3442544
• 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
• 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)CCCNC(=N)N)CCC(=O)O)[C@H](CC)C
• InChI: InChI=1S/C34H48N8O11/c1-5-18(2)30(42-25(43)11-13-28(47)52-4)33(51)41-23(10-12-27(45)46)31(49)38-17-26(44)40-22(7-6-14-37-34(35)36)32(50)39-20-8-9-21-19(3)15-29(48)53-24(21)16-20/h8-9,15-16,18,22-23,30H,5-7,10-14,17H2,1-4H3,(H,38,49)(H,39,50)(H,40,44)(H,41,51)(H,42,43)(H,45,46)(H4,35,36,37)/t18-,22-,23-,30-/m0/s1
• InChIKey: ZCGSBXYXFJJMTC-NVZQBYDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[({[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-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-[(4-methyl-2-oxochromen-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-AMC; MeOSuc-IEGR-AMC; MeOSuc-Ile-Glu-Gly-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105699
• PubChem CID: 25108610

CALCULATED PROPERTIES

• Acid pKa: 3.7104247
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -3.005672
• LogD (pH = 7.4): -2.9999764
• Log P: -3.000013
• Molar Refractivity: 198.8645 cm^3
• Polarizability: 72.336784 Å^3
• Polar Surface Area: 297.3 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC067

A fluorogenic substrate for Factor Xa.

REFERENCES

• Kato, M. et al., Throm. Res., 50:77 (1988).