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

• ChemBase ID: 106563
• Molecular Formular: C35H50N8O10
• Molecular Mass: 742.8191
• Monoisotopic Mass: 742.36498984
• 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)Nc1cc(OC)c2c(c1)cccc2
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)Nc1cc(OC)c2c(c1)cccc2)CCCNC(=N)N)CCC(=O)O)[C@H](CC)C
• InChI: InChI=1S/C35H50N8O10/c1-5-20(2)31(43-27(44)13-15-30(48)53-4)34(51)42-25(12-14-29(46)47)32(49)39-19-28(45)41-24(11-8-16-38-35(36)37)33(50)40-22-17-21-9-6-7-10-23(21)26(18-22)52-3/h6-7,9-10,17-18,20,24-25,31H,5,8,11-16,19H2,1-4H3,(H,39,49)(H,40,50)(H,41,45)(H,42,51)(H,43,44)(H,46,47)(H4,36,37,38)/t20-,24-,25-,31-/m0/s1
• InChIKey: XRCMHPWGEOFSNO-CEUFNZOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[({[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-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-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}methyl)carbamoyl]-4-[(2S,3S)-2-(4-methoxy-4-oxobutanamido)-3-methylpentanamido]butanoic acid
• Synonyms: Glut-Ile-Glu-Gly-Arg-MNA; Glut-IEGR-MNA; Glut-Ile-Glu-Gly-Arg-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105717
• PubChem CID: 25108717

CALCULATED PROPERTIES

• Acid pKa: 3.7104247
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -2.2833748
• LogD (pH = 7.4): -2.277677
• Log P: -2.2777069
• Molar Refractivity: 202.0053 cm^3
• Polarizability: 75.00279 Å^3
• Polar Surface Area: 280.23 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA067

A fluorogenic/colorimetric substrate for Factor Xa.

REFERENCES

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