N-Ac-Arg{N-omega-(N-methylcarbanoyl)}-N-methyl-Phe-OH

ID: ALA493316

PubChem CID: 24755478

Max Phase: Preclinical

Molecular Formula: C20H30N6O5

Molecular Weight: 434.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)NC(=N)NCCC[C@H](NC(C)=O)C(=O)N(C)[C@@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C20H30N6O5/c1-13(27)24-15(10-7-11-23-19(21)25-20(31)22-2)17(28)26(3)16(18(29)30)12-14-8-5-4-6-9-14/h4-6,8-9,15-16H,7,10-12H2,1-3H3,(H,24,27)(H,29,30)(H4,21,22,23,25,31)/t15-,16-/m0/s1

Standard InChI Key:  NXHZAKRRBAPHDQ-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -6.4256   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7111    0.3144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9966   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9966   -0.9231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2822    0.3144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677   -0.9231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8532    0.3144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1387   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    1.1394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098    1.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098    2.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.9231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336    0.3144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336    1.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626   -1.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336   -1.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915    0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770   -0.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  3  4  2  0
  3  5  1  0
  6  5  1  0
  6  7  2  0
  6  8  1  0
  9  8  1  0
  9 10  1  0
 11 10  1  0
 12 11  1  0
 12 13  1  6
 17 12  1  0
 14 13  1  0
 15 14  1  0
 14 16  2  0
 17 18  2  0
 17 19  1  0
 20 19  1  0
 21 19  1  1
 22 21  1  0
 25 21  1  0
 22 23  1  0
 22 24  2  0
 25 26  1  0
 27 26  2  0
 31 26  1  0
 28 27  1  0
 29 28  2  0
 29 30  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA493316

   (2s)-2-[[(2s)-2-Acetamido-5-[[n-(Methylcarbamoyl)carbamimidoyl]amino]pentanoyl]-Methyl-Amino]-3-Phenyl-Propanoic Acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 434.50

Molecular Weight (Monoisotopic): 434.2278

AlogP: -0.12

#Rotatable Bonds: 10

Polar Surface Area: 163.72

Molecular Species: ZWITTERION

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.03

CX Basic pKa: 9.51

CX LogP: -2.15

CX LogD: -2.15

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -0.04

References

1. Sunazuka T, Sugawara A, Iguchi K, Hirose T, Nagai K, Noguchi Y, Saito Y, Yamamoto T, Ui H, Gouda H, Shiomi K, Watanabe T, Omura S..  (2009)  Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide.,  17  (7): [PMID:19297173] [10.1016/j.bmc.2009.02.047]

2. Gouda H, Sunazuka T, Hirose T, Iguchi K, Yamaotsu N, Sugawara A, Noguchi Y, Saito Y, Yamamoto T, Watanabe T, Shiomi K, Omura S, Hirono S..  (2010)  NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin.,  18  (16): [PMID:20667742] [10.1016/j.bmc.2010.06.093]

Source

Source(1):

• Scientific Literature