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N6-(4-Isopropylphenyl)pyrido[2,3-d]pyrimidine-2,4,6-triamine

ID: ALA2382320

PubChem CID: 71680877

Max Phase: Preclinical

Molecular Formula: C16H18N6

Molecular Weight: 294.36

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(Nc2cnc3nc(N)nc(N)c3c2)cc1

Standard InChI:  InChI=1S/C16H18N6/c1-9(2)10-3-5-11(6-4-10)20-12-7-13-14(17)21-16(18)22-15(13)19-8-12/h3-9,20H,1-2H3,(H4,17,18,19,21,22)

Standard InChI Key:  NHLKIMKKGYOGCN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.0581  -12.5178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569  -13.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650  -13.7463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632  -12.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718  -12.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4726  -13.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1811  -13.7403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8894  -13.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8846  -12.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755  -12.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607  -11.2918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489  -13.7454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5898  -12.0945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000  -12.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3004  -13.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0097  -13.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7159  -13.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7083  -12.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9984  -12.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4266  -13.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4327  -14.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1313  -13.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  4 11  1  0
  2 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dhfr Dihydrofolate reductase (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dihydrofolate reductase (1239 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 294.36Molecular Weight (Monoisotopic): 294.1593AlogP: 3.06#Rotatable Bonds: 3
Polar Surface Area: 102.74Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 3.02CX LogP: 2.83CX LogD: 2.83
Aromatic Rings: 3Heavy Atoms: 22QED Weighted: 0.69Np Likeness Score: -1.01

References

1. Gangjee A, Namjoshi OA, Raghavan S, Queener SF, Kisliuk RL, Cody V..  (2013)  Design, synthesis, and molecular modeling of novel pyrido[2,3-d]pyrimidine analogues as antifolates; application of Buchwald-Hartwig aminations of heterocycles.,  56  (11): [PMID:23627352] [10.1021/jm400086g]

Source