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

ID: ALA41459

PubChem CID: 136046152

Max Phase: Preclinical

Molecular Formula: C21H29N6O7P

Molecular Weight: 508.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(O)CCC(NC(=O)c1ccc(NCC2CNc3nc(N)nc(O)c3C2)cc1)C(=O)O

Standard InChI:  InChI=1S/C21H29N6O7P/c1-2-34-35(32,33)8-7-16(20(30)31)25-18(28)13-3-5-14(6-4-13)23-10-12-9-15-17(24-11-12)26-21(22)27-19(15)29/h3-6,12,16,23H,2,7-11H2,1H3,(H,25,28)(H,30,31)(H,32,33)(H4,22,24,26,27,29)

Standard InChI Key:  GPUSXKHIVFTONZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    1.9917   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -2.5625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -2.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0375   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -4.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -3.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -3.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3292   -2.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7542   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -2.4375    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 19  1  0
  8  1  1  0
  9 14  1  0
 10  9  1  0
 11 12  1  0
 12 10  1  0
 13  3  1  0
 14 27  2  0
 15  5  1  0
 16 12  1  0
 17  7  2  0
 18  9  2  0
 19 16  1  0
 20 11  2  0
 21 24  1  0
 22  6  1  0
 23 30  1  0
 24  8  1  0
 25  7  1  0
 26 32  2  0
 27 33  1  0
 28  7  1  0
 29 23  1  0
 30 21  1  0
 31 11  1  0
 32 29  1  0
 33 29  2  0
 34 28  1  0
 35 34  1  0
  4  6  2  0
 13 21  1  0
 26 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA41459

   ---

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: 508.47

Molecular Weight (Monoisotopic): 508.1835

AlogP: 1.26

#Rotatable Bonds: 11

Polar Surface Area: 209.02

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.92

CX Basic pKa: 4.21

CX LogP: -1.76

CX LogD: -5.39

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: -0.01

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