6-[(4-Ethoxy-3-methoxy-phenylamino)-methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine

ID: ALA358195

PubChem CID: 44366644

Max Phase: Preclinical

Molecular Formula: C18H22N6O2

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(NCc2cnc3nc(N)nc(N)c3c2C)cc1OC

Standard InChI:  InChI=1S/C18H22N6O2/c1-4-26-13-6-5-12(7-14(13)25-3)21-8-11-9-22-17-15(10(11)2)16(19)23-18(20)24-17/h5-7,9,21H,4,8H2,1-3H3,(H4,19,20,22,23,24)

Standard InChI Key:  IOOOPIQISFLCNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.0250   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -4.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -5.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -5.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -4.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -3.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -5.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -4.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7375   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -3.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  3  1  0
  7  1  1  0
  8  4  1  0
  9 12  1  0
 10 11  1  0
 11 17  2  0
 12  7  2  0
 13 19  1  0
 14  9  1  0
 15 14  1  0
 16  5  1  0
 17 15  1  0
 18  6  1  0
 19 20  2  0
 20 17  1  0
 21 10  1  0
 22 13  1  0
 23  8  1  0
 24 22  1  0
 25 21  1  0
 26 24  1  0
  2  6  2  0
  8  9  2  0
 13 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA358195

   6-[(4-Ethoxy-3-methoxy-phenylamino)-methyl]-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine

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: 354.41

Molecular Weight (Monoisotopic): 354.1804

AlogP: 2.52

#Rotatable Bonds: 6

Polar Surface Area: 121.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.49

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.93

References

1. Debnath AK..  (2002)  Pharmacophore mapping of a series of 2,4-diamino-5-deazapteridine inhibitors of Mycobacterium avium complex dihydrofolate reductase.,  45  (1): [PMID:11754578] [10.1021/jm010360c]

Source

Source(1):

• Scientific Literature