2-{4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid

ID: ALA119674

PubChem CID: 135474705

Max Phase: Preclinical

Molecular Formula: C20H24N6O6

Molecular Weight: 444.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CNc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C20H24N6O6/c21-20-25-16-13(18(30)26-20)7-10(9-23-16)8-22-12-3-1-11(2-4-12)17(29)24-14(19(31)32)5-6-15(27)28/h1-4,10,14,22H,5-9H2,(H,24,29)(H,27,28)(H,31,32)(H4,21,23,25,26,30)

Standard InChI Key:  XQZVRAWIARJOCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.7875   -5.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -5.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -4.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -5.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -5.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5125   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -3.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9417   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0917   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5042   -2.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542   -1.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375   -5.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -4.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8042   -2.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -5.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6625   -3.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0750   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3792   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -1.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0917   -4.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0750   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  2  0
  6  2  1  0
  7  1  1  0
  8 13  1  0
  9  8  1  0
 10 12  1  0
 11  3  1  0
 12  9  1  0
 13 24  2  0
 14  5  1  0
 15 27  1  0
 16  8  2  0
 17 10  2  0
 18 22  1  0
 19  6  1  0
 20 28  1  0
 21 15  2  0
 22  7  1  0
 23 12  1  0
 24 32  1  0
 25 31  2  0
 26 20  1  0
 27 23  1  0
 28 18  1  0
 29 10  1  0
 30 15  1  0
 31 26  1  0
 32 26  2  0
  4  6  2  0
 18 11  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA119674

   ---

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: 444.45

Molecular Weight (Monoisotopic): 444.1757

AlogP: 0.51

#Rotatable Bonds: 9

Polar Surface Area: 199.79

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.23

CX Basic pKa: 4.38

CX LogP: -1.00

CX LogD: -6.08

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.04

References

1. Rosowsky A, Forsch RA, Null A, Moran RG..  (1999)  5-deazafolate analogues with a rotationally restricted glutamate or ornithine side chain: synthesis and binding interaction with folylpolyglutamate synthetase.,  42  (18): [PMID:10479284] [10.1021/jm9807205]

Source

Source(1):

• Scientific Literature