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4-[(2-Amino-4-hydroxy-5-methyl-quinazolin-6-ylamino)-methyl]-benzoic acid

ID: ALA155679

PubChem CID: 136191440

Max Phase: Preclinical

Molecular Formula: C17H16N4O3

Molecular Weight: 324.34

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1c(NCc2ccc(C(=O)O)cc2)ccc2nc(N)nc(O)c12

Standard InChI:  InChI=1S/C17H16N4O3/c1-9-12(6-7-13-14(9)15(22)21-17(18)20-13)19-8-10-2-4-11(5-3-10)16(23)24/h2-7,19H,8H2,1H3,(H,23,24)(H3,18,20,21,22)

Standard InChI Key:  VJZKCZZSIUMGGC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.7125   -1.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -3.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167    1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -1.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4042    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1125    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -3.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8375    0.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  6  2  0
  6  4  1  0
  7  3  1  0
  8 11  1  0
  9  7  2  0
 10  9  1  0
 11 17  2  0
 12  5  1  0
 13  8  2  0
 14 12  2  0
 15  2  1  0
 16  4  1  0
 17 23  1  0
 18 22  2  0
 19 10  1  0
 20  8  1  0
 21 19  1  0
 22 21  1  0
 23 21  2  0
 24  7  1  0
  3  5  1  0
 14  9  1  0
 18 11  1  0
M  END

Alternative Forms

  1. Parent:

    ALA155679

    ---

Associated Targets(Human)

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

Associated Targets(non-human)

Tyms Thymidylate synthase (842 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
thyA Thymidylate synthase (501 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: 324.34Molecular Weight (Monoisotopic): 324.1222AlogP: 2.54#Rotatable Bonds: 4
Polar Surface Area: 121.36Molecular Species: ACIDHBA: 6HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 4.09CX Basic pKa: 2.87CX LogP: 2.63CX LogD: -0.19
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.58Np Likeness Score: -0.83

References

1. Crippen GM..  (1980)  Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors.,  23  (6): [PMID:7392027] [10.1021/jm00180a004]
2. Ghose AK, Crippen GM..  (1982)  Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors.,  25  (8): [PMID:7120278] [10.1021/jm00350a003]
3. Chen BK, Horváth C, Bertino JR..  (1979)  Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.,  22  (5): [PMID:110930] [10.1021/jm00191a005]

Source