US8835445, 39

ID: ALA3686070

PubChem CID: 67889371

Max Phase: Preclinical

Molecular Formula: C21H22N6O2S

Molecular Weight: 422.51

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)OC(C)(C)C)nc(-c2cccs2)n1-c1ccc2c(N)nc(N)nc2c1

Standard InChI:  InChI=1S/C21H22N6O2S/c1-11-16(19(28)29-21(2,3)4)25-18(15-6-5-9-30-15)27(11)12-7-8-13-14(10-12)24-20(23)26-17(13)22/h5-10H,1-4H3,(H4,22,23,24,26)

Standard InChI Key:  SARLNVLIFJQCFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    1.8365   -3.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    0.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273    2.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669    1.0635    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9363   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111   -4.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059   -5.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3037   -4.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9148   -6.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1082   -6.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4029   -7.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2096   -7.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  5 11  1  0
 11  2  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 15  1  0
 22 23  2  0
 23 12  1  0
  3 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Associated Targets(Human)

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

Associated Targets(non-human)

folA Dihydrofolate reductase (367 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 422.51Molecular Weight (Monoisotopic): 422.1525AlogP: 3.97#Rotatable Bonds: 3
Polar Surface Area: 121.94Molecular Species: NEUTRALHBA: 9HBD: 2
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 6.82CX LogP: 4.05CX LogD: 3.95
Aromatic Rings: 4Heavy Atoms: 30QED Weighted: 0.48Np Likeness Score: -1.27

References

1.  (2014)  Dihydrofolate reductase inhibitors, 

Source

Source(1):