ID: ALA19383

Max Phase: Preclinical

Molecular Formula: C13H17N5

Molecular Weight: 243.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C)c1ccc(Cc2cnc(N)nc2N)cc1

Standard InChI:  InChI=1S/C13H17N5/c1-18(2)11-5-3-9(4-6-11)7-10-8-16-13(15)17-12(10)14/h3-6,8H,7H2,1-2H3,(H4,14,15,16,17)

Standard InChI Key:  XXIDWUQHWYJBMQ-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: 243.31

Molecular Weight (Monoisotopic): 243.1484

AlogP: 1.30

#Rotatable Bonds: 3

Polar Surface Area: 81.06

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: 1.86

CX LogD: 1.67

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.85

Np Likeness Score: -0.65

References

1. Dietrich SW, Blaney JM, Reynolds MA, Jow PY, Hansch C..  (1980)  Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines.,  23  (11): [PMID:7005446] [10.1021/jm00185a011]

2. 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]

3. 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]

4. 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]

5. 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]

6. 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]

7. Ghose AK, Crippen GM..  (1985)  Use of physicochemical parameters in distance geometry and related three-dimensional quantitative structure-activity relationships: a demonstration using Escherichia coli dihydrofolate reductase inhibitors.,  28  (3): [PMID:3882967] [10.1021/jm00381a013]

8. 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]

9. 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]

10. 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]

11. 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]

12. 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]

13. 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]

14. 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]

15. Hopfinger AJ..  (1981)  Inhibition of dihydrofolate reductase: structure-activity correlations of 2,4-diamino-5-benzylpyrimidines based upon molecular shape analysis.,  24  (7): [PMID:7277386] [10.1021/jm00139a010]

16. Hopfinger AJ..  (1983)  Theory and application of molecular potential energy fields in molecular shape analysis: a quantitative structure--activity relationship study of 2,4-diamino-5-benzylpyrimidines as dihydrofolate reductase inhibitors.,  26  (7): [PMID:6345782] [10.1021/jm00361a011]

17. Blaney JM, Dietrich SW, Reynolds MA, Hansch C..  (1979)  Quantitative structure-activity relationship of 5-(X-benzyl)-2,4-diaminopyrimidines inhibiting bovine liver dihydrofolate reductase.,  22  (6): [PMID:458817] [10.1021/jm00192a003]

Source

Source(1):

• Scientific Literature