2-(4-(2-amino-4-hydroxy-8-oxo-6H-pyrrolo[3,4-g]pteridin-7(8H)-yl)benzamido)pentanedioic acid

ID: ALA377466

PubChem CID: 135437382

Max Phase: Preclinical

Molecular Formula: C20H17N7O7

Molecular Weight: 467.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2nc3c(nc2n1)C(=O)N(c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)C3

Standard InChI:  InChI=1S/C20H17N7O7/c21-20-25-15-14(17(31)26-20)22-11-7-27(18(32)13(11)24-15)9-3-1-8(2-4-9)16(30)23-10(19(33)34)5-6-12(28)29/h1-4,10H,5-7H2,(H,23,30)(H,28,29)(H,33,34)(H3,21,24,25,26,31)

Standard InChI Key:  KRSGNZLDIIQEHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.4272    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -0.2947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -0.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215    0.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    0.9427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530    0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101   -0.7081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040   -0.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1040    0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    0.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    0.9433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890   -0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    0.1193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    0.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    1.5681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975    0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -0.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    0.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5948    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739    0.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0864    0.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0864   -0.5930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9114   -0.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3239    0.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1489    0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5626    0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3876    0.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513    1.5462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3233   -1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102   -2.0220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1483   -1.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -1.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  5  1  0
  7 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
 15 16  2  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  1  1  0
  1 21  2  0
 21 17  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  2  3  2  0
 27 28  1  0
  3  4  1  0
 28 29  1  0
  4  5  2  0
 28 30  2  0
  5  6  1  0
 25 31  1  0
  6  7  2  0
 31 32  2  0
  7  2  1  0
 31 33  1  0
  4  8  1  0
  3 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA377466

   ---

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: 467.40

Molecular Weight (Monoisotopic): 467.1189

AlogP: -0.08

#Rotatable Bonds: 7

Polar Surface Area: 221.82

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.12

CX Basic pKa: ┄

CX LogP: -0.22

CX LogD: -6.89

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -0.47

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