N-Ac-Asp-D-Ala-Arg{N-omega-(N-methylcarbanoyl)}-OH

ID: ALA492714

PubChem CID: 44572708

Max Phase: Preclinical

Molecular Formula: C17H29N7O8

Molecular Weight: 459.46

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H29N7O8/c1-8(21-14(29)11(7-12(26)27)22-9(2)25)13(28)23-10(15(30)31)5-4-6-20-16(18)24-17(32)19-3/h8,10-11H,4-7H2,1-3H3,(H,21,29)(H,22,25)(H,23,28)(H,26,27)(H,30,31)(H4,18,19,20,24,32)/t8-,10+,11+/m1/s1

Standard InChI Key:  ABYZFXCZXNIHDL-MIMYLULJSA-N

Molfile:  

     RDKit          2D

 32 31  0  0  0  0  0  0  0  0999 V2000
   16.9513  -19.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6658  -19.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3802  -19.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6658  -20.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9513  -21.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3802  -21.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0947  -19.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8092  -19.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5237  -19.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2381  -19.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9526  -19.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2381  -18.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6671  -19.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3815  -19.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6671  -18.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3815  -20.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9513  -18.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2368  -18.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6658  -18.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2368  -17.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5224  -18.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9513  -16.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9513  -16.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6658  -17.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6658  -15.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2368  -15.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2368  -14.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5224  -14.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9513  -14.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3802  -16.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3820  -16.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0965  -15.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0
  8  9  1  0
 17 18  1  0
  4  5  1  0
 17 19  2  0
  9 10  1  0
 18 20  1  0
  2  3  1  1
 18 21  1  1
 10 11  1  0
 20 22  1  0
  4  6  2  0
 22 23  1  0
 10 12  2  0
 22 24  2  0
  1  2  1  0
 23 25  1  1
 11 13  1  0
 23 26  1  0
  3  7  1  0
 26 27  1  0
 13 14  1  0
 27 28  1  0
  2  4  1  0
 27 29  2  0
 13 15  2  0
 25 30  1  0
  7  8  1  0
 14 16  1  0
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA492714

   N-Ac-Asp-D-Ala-Arg{N-omega-(N-methylcarbanoyl)}-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.46

Molecular Weight (Monoisotopic): 459.2078

AlogP: -2.73

#Rotatable Bonds: 12

Polar Surface Area: 238.91

Molecular Species: ZWITTERION

HBA: 7

HBD: 9

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.58

CX Basic pKa: 9.67

CX LogP: -5.58

CX LogD: -8.43

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.08

Np Likeness Score: 0.09

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]

Source

Source(1):

• Scientific Literature