2-{4-[(2-Amino-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-4-sulfo-butyric acid

ID: ALA39175

PubChem CID: 135887105

Max Phase: Preclinical

Molecular Formula: C19H20N6O7S

Molecular Weight: 476.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2cc(CNc3ccc(C(=O)NC(CCS(=O)(=O)O)C(=O)O)cc3)cnc2n1

Standard InChI:  InChI=1S/C19H20N6O7S/c20-19-24-15-13(17(27)25-19)7-10(9-22-15)8-21-12-3-1-11(2-4-12)16(26)23-14(18(28)29)5-6-33(30,31)32/h1-4,7,9,14,21H,5-6,8H2,(H,23,26)(H,28,29)(H,30,31,32)(H3,20,22,24,25,27)

Standard InChI Key:  DEZOURQTRLKTPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.8833   -2.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000   -1.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -0.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -2.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -0.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -0.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8542   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -0.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    0.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -2.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -1.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -1.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    0.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  2  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7 19  1  0
  8 16  1  0
  9  3  1  0
 10  8  1  0
 11 12  1  0
 12 10  1  0
 13  5  1  0
 14  7  2  0
 15  7  2  0
 16 27  2  0
 17  4  1  0
 18 12  1  0
 19 18  1  0
 20  8  2  0
 21 26  1  0
 22 11  2  0
 23  6  1  0
 24 30  1  0
 25  7  1  0
 26  9  2  0
 27 33  1  0
 28 32  2  0
 29 24  1  0
 30 21  1  0
 31 11  1  0
 32 29  1  0
 33 29  2  0
  4  5  2  0
 13 21  2  0
 16 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA39175

   ---

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: 476.47

Molecular Weight (Monoisotopic): 476.1114

AlogP: 0.39

#Rotatable Bonds: 9

Polar Surface Area: 217.72

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.06

CX Basic pKa: 3.55

CX LogP: -0.87

CX LogD: -6.11

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.68

References

1. Rosowsky A, Forsch RA, Reich VE, Freisheim JH, Moran RG..  (1992)  Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: synthesis and in vitro biological evaluation.,  35  (9): [PMID:1578484] [10.1021/jm00087a012]

Source

Source(1):

• Scientific Literature