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

ID: ALA150382

PubChem CID: 470202

Max Phase: Preclinical

Molecular Formula: C16H17BrN6

Molecular Weight: 373.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NCc2cnc3nc(N)nc(N)c3c2C)ccc1Br

Standard InChI:  InChI=1S/C16H17BrN6/c1-8-5-11(3-4-12(8)17)20-6-10-7-21-15-13(9(10)2)14(18)22-16(19)23-15/h3-5,7,20H,6H2,1-2H3,(H4,18,19,21,22,23)

Standard InChI Key:  YIWKNSVDJMQTLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  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
    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
    5.3042   -4.2917    0.0000 C   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
   -1.1208   -5.5542    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
    5.2917   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -2.6292    0.0000 Br  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
    1.7292   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -4.2792    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 11  1  0
 10 15  1  0
 11  7  2  0
 12 19  1  0
 13  9  1  0
 14 13  1  0
 15 18  2  0
 16  5  1  0
 17  6  1  0
 18 14  1  0
 19 21  2  0
 20 12  1  0
 21 18  1  0
 22  8  1  0
 23 10  1  0
  6  2  2  0
  9  8  2  0
 12 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA150382

   6-[(4-Bromo-3-methyl-anilino)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: 373.26

Molecular Weight (Monoisotopic): 372.0698

AlogP: 3.18

#Rotatable Bonds: 3

Polar Surface Area: 102.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.84

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -1.11

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