(R)-2-(2-(4,6-dichloro-1,3,5-triazin-2-ylamino)benzamido)propanoic acid

ID: ALA1836532

PubChem CID: 46179764

Max Phase: Preclinical

Molecular Formula: C13H11Cl2N5O3

Molecular Weight: 356.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)c1ccccc1Nc1nc(Cl)nc(Cl)n1)C(=O)O

Standard InChI:  InChI=1S/C13H11Cl2N5O3/c1-6(10(22)23)16-9(21)7-4-2-3-5-8(7)17-13-19-11(14)18-12(15)20-13/h2-6H,1H3,(H,16,21)(H,22,23)(H,17,18,19,20)/t6-/m1/s1

Standard InChI Key:  DUGNJAKXRAXNTI-ZCFIWIBFSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    5.7282   -7.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122   -7.8368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0121   -8.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7272   -9.0742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439   -8.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4406   -7.8342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1599   -9.0669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1631   -9.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4477  -10.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4505  -11.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671  -11.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8823  -11.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8761  -10.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5876   -9.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3051  -10.2841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5816   -9.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0165   -9.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7340  -10.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4454   -9.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7400  -11.0987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0105   -9.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -6.6003    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2975   -9.0734    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 11 12  1  0
  6  1  2  0
 12 13  2  0
 13  8  1  0
  1  2  1  0
  5  7  1  0
  3  4  1  0
 14 15  1  0
 14 16  2  0
 13 14  1  0
  7  8  1  0
 15 17  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
  4  5  2  0
 18 20  2  0
  9 10  1  0
 17 21  1  6
  2  3  2  0
  1 22  1  0
 10 11  2  0
  3 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1836532

   (2R)-2-[[2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzoyl]amino]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: 356.17

Molecular Weight (Monoisotopic): 355.0239

AlogP: 2.12

#Rotatable Bonds: 5

Polar Surface Area: 117.10

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.80

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 0.72

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -1.12

References

1. Sosič I, Mirković B, Turk S, Štefaneb B, Kos J, Gobec S..  (2011)  Discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B.,  46  (9): [PMID:21849222] [10.1016/j.ejmech.2011.08.005]

Source

Source(1):

• Scientific Literature