5-Amino-2-{4-[(2,4-diamino-pyrido[3,2-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

ID: ALA35921

PubChem CID: 10070986

Max Phase: Preclinical

Molecular Formula: C20H24N8O3

Molecular Weight: 424.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(NCc2ccc3nc(N)nc(N)c3n2)cc1)C(=O)O

Standard InChI:  InChI=1S/C20H24N8O3/c21-9-1-2-15(19(30)31)26-18(29)11-3-5-12(6-4-11)24-10-13-7-8-14-16(25-13)17(22)28-20(23)27-14/h3-8,15,24H,1-2,9-10,21H2,(H,26,29)(H,30,31)(H4,22,23,27,28)

Standard InChI Key:  DMZXWJBUCKJAOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    1.4792   -9.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -9.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -8.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -9.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917  -10.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -8.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -7.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -9.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3250   -7.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0292   -6.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917   -7.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6000   -6.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -6.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -9.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -9.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250  -10.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -7.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625  -10.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -8.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750   -7.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -8.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7417   -6.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -8.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -9.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4792   -9.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7542   -7.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4792   -8.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7542   -8.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  2  1  0
  7 12  1  0
  8  5  1  0
  9  7  1  0
 10 11  1  0
 11  9  1  0
 12 20  2  0
 13  7  2  0
 14 10  2  0
 15 24  1  0
 16  6  2  0
 17  8  1  0
 18  3  1  0
 19  4  1  0
 20 27  1  0
 21 26  2  0
 22 15  1  0
 23 10  1  0
 24 16  1  0
 25 17  2  0
 26 22  1  0
 27 22  2  0
 28 30  1  0
 29 11  1  0
 30 31  1  0
 31 29  1  0
  2  8  2  0
 25 16  1  0
 21 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA35921

   5-Amino-2-{4-[(2,4-diamino-pyrido[3,2-d]pyrimidin-6-ylmethyl)-amino]-benzoylamino}-pentanoic acid

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: 424.47

Molecular Weight (Monoisotopic): 424.1971

AlogP: 0.72

#Rotatable Bonds: 9

Polar Surface Area: 195.16

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.78

CX Basic pKa: 9.90

CX LogP: -2.23

CX LogD: -2.23

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: -0.49

References

1. Rosowsky A, Forsch RA, Bader H, Freisheim JH..  (1991)  Synthesis and in vitro biological activity of new deaza analogues of folic acid, aminopterin, and methotrexate with an L-ornithine side chain.,  34  (4): [PMID:2016722] [10.1021/jm00108a032]

2. 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