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

ID: ALA40850

PubChem CID: 135887103

Max Phase: Preclinical

Molecular Formula: C19H21N6O7P

Molecular Weight: 476.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21N6O7P/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)(H2,30,31,32)(H3,20,22,24,25,27)

Standard InChI Key:  OIGOTHHCNXEMSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    0.1917   -3.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -1.7417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -1.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9375   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -3.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0417   -1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -0.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -2.6750    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 20  1  0
  8 14  1  0
  9  3  1  0
 10  8  1  0
 11 12  1  0
 12 10  1  0
 13  5  1  0
 14 27  2  0
 15  4  1  0
 16 12  1  0
 17  7  2  0
 18  8  2  0
 19 24  1  0
 20 16  1  0
 21 11  2  0
 22  6  1  0
 23 30  1  0
 24  9  2  0
 25  7  1  0
 26  7  1  0
 27 33  1  0
 28 32  2  0
 29 23  1  0
 30 19  1  0
 31 11  1  0
 32 29  1  0
 33 29  2  0
  4  5  2  0
 13 19  2  0
 28 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA40850

   ---

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: 476.39

Molecular Weight (Monoisotopic): 476.1209

AlogP: 0.68

#Rotatable Bonds: 9

Polar Surface Area: 220.88

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.74

CX Basic pKa: 2.69

CX LogP: -1.58

CX LogD: -6.27

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.56

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