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

ID: ALA151129

PubChem CID: 464028

Max Phase: Preclinical

Molecular Formula: C18H22N6O3

Molecular Weight: 370.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCc1c(CNc2ccc(OC)c(OC)c2)cnc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C18H22N6O3/c1-25-9-12-10(8-22-17-15(12)16(19)23-18(20)24-17)7-21-11-4-5-13(26-2)14(6-11)27-3/h4-6,8,21H,7,9H2,1-3H3,(H4,19,20,22,23,24)

Standard InChI Key:  FBYMQKFBKBGAIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    1.7292   -3.0667    0.0000 C   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
    2.4417   -2.6542    0.0000 O   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   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -1.8292    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  8  1  0
 23 13  1  0
 24 22  1  0
 25 21  1  0
 26 23  1  0
 27 24  1  0
  2  6  2  0
  8  9  2  0
 13 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA151129

   6-[(3,4-Dimethoxy-phenylamino)-methyl]-5-methoxymethyl-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: 370.41

Molecular Weight (Monoisotopic): 370.1753

AlogP: 1.96

#Rotatable Bonds: 7

Polar Surface Area: 130.43

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.49

CX LogP: 0.91

CX LogD: 0.90

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -0.71

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