(S)-2-(2-amino-4-oxo-3,4-dihydropteridine-7-carboxamido)-4-phenylbutanoic acid

ID: ALA4789697

PubChem CID: 162670156

Max Phase: Preclinical

Molecular Formula: C17H16N6O4

Molecular Weight: 368.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc2nc(C(=O)N[C@@H](CCc3ccccc3)C(=O)O)cnc2c(=O)[nH]1

Standard InChI:  InChI=1S/C17H16N6O4/c18-17-22-13-12(15(25)23-17)19-8-11(20-13)14(24)21-10(16(26)27)7-6-9-4-2-1-3-5-9/h1-5,8,10H,6-7H2,(H,21,24)(H,26,27)(H3,18,20,22,23,25)/t10-/m0/s1

Standard InChI Key:  CHPGDIWMRACXGP-JTQLQIEISA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.3822  -10.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9688   -8.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3682   -9.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820  -10.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2163   -8.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1105  -11.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3264   -6.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4091  -11.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866   -6.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -6.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9282   -7.7637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2163   -8.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0575   -8.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0986   -7.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3403   -7.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6413   -8.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6553   -8.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866   -5.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955   -8.1599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0986   -6.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866   -8.1551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6955  -11.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6785   -7.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0934  -10.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8026   -6.5181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -7.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6785   -6.9258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 27 23  1  0
 23  2  1  0
 26 10  1  0
 27  9  1  0
 17  3  1  0
  1  4  2  0
 15  7  1  0
  6 24  2  0
 20 14  2  0
 12  5  2  0
 14 19  1  0
 16 17  1  6
 20 25  1  0
 26 12  1  0
  9 20  1  0
 16 11  1  0
  4 22  1  0
 22  8  2  0
  3  1  1  0
 23 21  2  0
 19 26  2  0
 10 25  2  0
  9 18  2  0
 15 13  2  0
 12 11  1  0
 16 15  1  0
 21 14  1  0
 24  1  1  0
  8  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789697

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 368.35

Molecular Weight (Monoisotopic): 368.1233

AlogP: 0.11

#Rotatable Bonds: 6

Polar Surface Area: 163.95

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.95

CX Basic pKa: ┄

CX LogP: 0.65

CX LogD: -2.83

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.25

References

1. Saito R,Suzuki S,Sasaki K.  (2016)  Pterin-7-carboxamides as a new class of aldose reductase inhibitors.,  26  (20.0): [PMID:27666634] [10.1016/j.bmcl.2016.09.033]

Source

Source(1):

• Scientific Literature