ID: ALA31547

Max Phase: Preclinical

Molecular Formula: C17H24N4O

Molecular Weight: 300.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCCCOc1cccc(Cc2cnc(N)nc2N)c1

Standard InChI:  InChI=1S/C17H24N4O/c1-2-3-4-5-9-22-15-8-6-7-13(11-15)10-14-12-20-17(19)21-16(14)18/h6-8,11-12H,2-5,9-10H2,1H3,(H4,18,19,20,21)

Standard InChI Key:  FBTWFHMLKCKSPR-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: 300.41

Molecular Weight (Monoisotopic): 300.1950

AlogP: 3.19

#Rotatable Bonds: 8

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: 3.81

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.37

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. Coats EA, Genther CS, Selassie CD, Strong CD, Hansch C..  (1985)  Quantitative structure-activity relationship of antifolate inhibition of bacteria cell cultures resistant and sensitive to methotrexate.,  28  (12): [PMID:3934385] [10.1021/jm00150a026]

4. 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]

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. Chowdhury SF, Villamor VB, Guerrero RH, Leal I, Brun R, Croft SL, Goodman JM, Maes L, Ruiz-Perez LM, Pacanowska DG, Gilbert IH..  (1999)  Design, synthesis, and evaluation of inhibitors of trypanosomal and leishmanial dihydrofolate reductase.,  42  (21): [PMID:10543874] [10.1021/jm981130+]

8. 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]

9. 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]

10. 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]

11. 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]

12. 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]

13. 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