4-[{2-[2-(acetylamino)-4-hydroxypteridin-6-yl]ethyl}(methyl)amino]benzoic acid

ID: ALA209381

PubChem CID: 135441514

Max Phase: Preclinical

Molecular Formula: C18H18N6O4

Molecular Weight: 382.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1nc(O)c2nc(CCN(C)c3ccc(C(=O)O)cc3)cnc2n1

Standard InChI:  InChI=1S/C18H18N6O4/c1-10(25)20-18-22-15-14(16(26)23-18)21-12(9-19-15)7-8-24(2)13-5-3-11(4-6-13)17(27)28/h3-6,9H,7-8H2,1-2H3,(H,27,28)(H2,19,20,22,23,25,26)

Standard InChI Key:  CLUYOQSENFIUNI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   12.7024   -9.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9912   -8.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7024  -10.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4178  -10.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1331  -10.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1331   -9.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4178   -9.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8443  -10.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5596  -10.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8443  -11.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9912   -9.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4178  -12.0023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332  -11.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332  -10.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4178  -10.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025  -10.7657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025  -11.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8485  -12.0023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8485  -10.3535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8485   -9.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332   -9.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4178   -9.5291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913  -12.0023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5597   -9.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2760  -11.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2760  -10.7657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2744   -9.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617  -12.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  1  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
 11  1  1  0
 11  2  1  0
  1  3  2  0
  3  4  1  0
  4  5  2  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 13 18  1  0
 14 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 15  2  0
 17 23  1  0
 20 24  1  0
 23 25  1  0
 25 26  2  0
  5  6  1  0
 24 27  1  0
 27 11  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209381

   ---

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: 382.38

Molecular Weight (Monoisotopic): 382.1390

AlogP: 1.46

#Rotatable Bonds: 6

Polar Surface Area: 141.43

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.75

CX Basic pKa: 3.24

CX LogP: 1.55

CX LogD: -0.91

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.12

References

1. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N..  (2006)  Discovery of small molecule integrin alphavbeta3 antagonists as novel anticancer agents.,  49  (15): [PMID:16854058] [10.1021/jm051296s]

Source

Source(1):

• Scientific Literature