(R)-5-amino-2-((R)-3-(2-amino-5-chlorobenzamido)-5-methylhexanamido)-5-oxopentanoic acid

ID: ALA525090

PubChem CID: 44592579

Max Phase: Preclinical

Molecular Formula: C19H27ClN4O5

Molecular Weight: 426.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](CC(=O)N[C@H](CCC(N)=O)C(=O)O)NC(=O)c1cc(Cl)ccc1N

Standard InChI:  InChI=1S/C19H27ClN4O5/c1-10(2)7-12(23-18(27)13-8-11(20)3-4-14(13)21)9-17(26)24-15(19(28)29)5-6-16(22)25/h3-4,8,10,12,15H,5-7,9,21H2,1-2H3,(H2,22,25)(H,23,27)(H,24,26)(H,28,29)/t12-,15-/m1/s1

Standard InChI Key:  UOZUSJLHWRIHGK-IUODEOHRSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    8.9527   -4.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9516   -4.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6664   -5.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3828   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3800   -4.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6646   -3.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2382   -3.7418    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0980   -5.3924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0929   -3.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8089   -4.1451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0898   -2.9103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5218   -3.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2378   -4.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9508   -3.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9476   -2.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6668   -4.1343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5187   -2.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2316   -2.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2285   -1.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0250   -2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3797   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0957   -4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3766   -2.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0895   -2.4790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6606   -2.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0988   -4.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8148   -5.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5277   -4.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8179   -6.1888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
 14 15  2  0
  3  4  2  0
 14 16  1  0
  4  8  1  0
 12 17  1  6
 17 18  1  0
  5  9  1  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
  9 10  1  0
 16 21  1  0
  2  3  1  0
 21 22  1  1
  9 11  2  0
 21 23  1  0
  5  6  2  0
 23 24  1  0
 10 12  1  0
 23 25  2  0
  6  1  1  0
 22 26  1  0
 12 13  1  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 13 14  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA525090

   (2R)-5-amino-2-[[(3R)-3-[(2-amino-5-chlorobenzoyl)amino]-5-methylhexanoyl]amino]-5-oxopentanoic 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: 426.90

Molecular Weight (Monoisotopic): 426.1670

AlogP: 1.29

#Rotatable Bonds: 11

Polar Surface Area: 164.61

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.67

CX Basic pKa: 2.14

CX LogP: 1.02

CX LogD: -2.16

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.29

References

1. Zhang L, Yan Y, Liu Z, Abliz Z, Liu G..  (2009)  Identification of peptide substrate and small molecule inhibitors of testis-specific serine/threonine kinase1 (TSSK1) by the developed assays.,  52  (14): [PMID:19530700] [10.1021/jm9002846]

Source

Source(1):

• Scientific Literature