ID: ALA281760

Max Phase: Preclinical

Molecular Formula: C16H22N4O

Molecular Weight: 286.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCOCc1cccc(Cc2cnc(N)nc2N)c1

Standard InChI:  InChI=1S/C16H22N4O/c1-2-3-7-21-11-13-6-4-5-12(8-13)9-14-10-19-16(18)20-15(14)17/h4-6,8,10H,2-3,7,9,11H2,1H3,(H4,17,18,19,20)

Standard InChI Key:  XEJJIPLFLDZYDR-UHFFFAOYSA-N

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

Properties

Molecular Weight: 286.38

Molecular Weight (Monoisotopic): 286.1794

AlogP: 2.55

#Rotatable Bonds: 7

Polar Surface Area: 87.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.16

CX LogP: 2.96

CX LogD: 2.77

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.76

Np Likeness Score: -0.44

References

1. Doweyko AM..  (1988)  The hypothetical active site lattice. An approach to modelling active sites from data on inhibitor molecules.,  31  (7): [PMID:3290487] [10.1021/jm00402a025]

2. Selassie CD, Fang ZX, Li RL, Hansch C, Debnath G, Klein TE, Langridge R, Kaufman BT..  (1989)  On the structure selectivity problem in drug design. A comparative study of benzylpyrimidine inhibition of vertebrate and bacterial dihydrofolate reductase via molecular graphics and quantitative structure-activity relationships.,  32  (8): [PMID:2502631] [10.1021/jm00128a035]

3. Loukas YL..  (2001)  Adaptive neuro-fuzzy inference system: an instant and architecture-free predictor for improved QSAR studies.,  44  (17): [PMID:11495588] [10.1021/jm000226c]

4. Crippen GM..  (1997)  Validation of EGSITE2, a mixed integer program for deducing objective site models for experimental binding data.,  40  (20): [PMID:9379435] [10.1021/jm970211n]

5. So SS, Richards WG..  (1992)  Application of neural networks: quantitative structure-activity relationships of the derivatives of 2,4-diamino-5-(substituted-benzyl)pyrimidines as DHFR inhibitors.,  35  (17): [PMID:1507206] [10.1021/jm00095a016]

6. Li RL, Poe M..  (1988)  Quantitative structure-activity relationships for the inhibition of Escherichia coli dihydrofolate reductase by 5-(substituted benzyl)-2,4-diaminopyrimidines.,  31  (2): [PMID:3276891] [10.1021/jm00397a017]

7. Li R, Hansch C, Kaufman BT..  (1982)  A comparison of the inhibitory action of 5-(substituted-benzyl)-2,4-diaminopyrimidines on dihydrofolate reductase from chicken liver with that from bovine liver.,  25  (4): [PMID:7069722] [10.1021/jm00346a020]

8. Selassie CD, Li R, Hansch C, Khwaja TA, Dias CB..  (1982)  Inhibition by 5-(substituted-benzyl)-2,4-diaminopyrimidines of murine tumor (L5178Y) cell cultures sensitive to and resistant to methotrexate. Further evidence for the sensitivity of resistant cells to hydrophobic drugs.,  25  (5): [PMID:7086836] [10.1021/jm00347a007]

9. Selassie CD, Li RL, Poe M, Hansch C..  (1991)  On the optimization of hydrophobic and hydrophilic substituent interactions of 2,4-diamino-5-(substituted-benzyl)pyrimidines with dihydrofolate reductase.,  34  (1): [PMID:1899453] [10.1021/jm00105a008]

10. Li RL, Dietrich SW, Hansch C..  (1981)  Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines.,  24  (5): [PMID:7017146] [10.1021/jm00137a012]

11. Selassie CD, Fang ZX, Li RL, Hansch C, Klein T, Langridge R, Kaufman BT..  (1986)  Inhibition of chicken liver dihydrofolate reductase by 5-(substituted benzyl)-2,4-diaminopyrimidines. A quantitative structure-activity relationship and graphics analysis.,  29  (5): [PMID:3701780] [10.1021/jm00155a006]

12. Hansch C, Li R, Blaney JM, Langridge R..  (1982)  Comparison of the inhibition of Escherichia coli and Lactobacillus casei dihydrofolate reductase by 2,4-diamino-5-(substituted-benzyl)pyrimidines: quantitative structure-activity relationships, X-ray crystallography, and computer graphics in structure-activity analysis.,  25  (7): [PMID:6809941] [10.1021/jm00349a003]

Source

Source(1):

• Scientific Literature