ID: ALA266025

Max Phase: Preclinical

Molecular Formula: C19H23N5O2

Molecular Weight: 353.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1(C)N=C(N)N=C(N)N1c1cccc(OCCOc2ccccc2)c1

Standard InChI:  InChI=1S/C19H23N5O2/c1-19(2)23-17(20)22-18(21)24(19)14-7-6-10-16(13-14)26-12-11-25-15-8-4-3-5-9-15/h3-10,13H,11-12H2,1-2H3,(H4,20,21,22,23)

Standard InChI Key:  FLSFYHOJHGHMRO-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: 353.43

Molecular Weight (Monoisotopic): 353.1852

AlogP: 2.33

#Rotatable Bonds: 6

Polar Surface Area: 98.46

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.02

CX LogP: 2.58

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -0.65

References

1. Ghose AK, Crippen GM..  (1983)  Combined distance geometry analysis of dihydrofolate reductase inhibition by quinazolines and triazines.,  26  (7): [PMID:6864738] [10.1021/jm00361a012]

2. Coats EA, Genther CS, Dietrich SW, Guo ZR, Hansch C..  (1981)  Comparison of the inhibition of methotrexate-sensitive and -resistant Lactobacillus casei cell cultures with purified Lactobacillus casei dihydrofolate reductase by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(3-substituted-phenyl)-s-triazines. Use of quantitative structure-activity relationships in making inferences about the mechanism of resistance and the structure of the enzyme is situ compared with the enzyme in vitro.,  24  (12): [PMID:6796688] [10.1021/jm00144a010]

3. Hansch C, Hathaway BA, Guo ZR, Selassie CD, Dietrich SW, Blaney JM, Langridge R, Volz KW, Kaufman BT..  (1984)  Crystallography, quantitative structure-activity relationships, and molecular graphics in a comparative analysis of the inhibition of dihydrofolate reductase from chicken liver and Lactobacillus casei by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazine s.,  27  (2): [PMID:6420569] [10.1021/jm00368a006]

4. Khwaja TA, Pentecost S, Selassie CD, Guo Z, Hansch C..  (1982)  Comparison of quantitative structure-activity relationships of the inhibition of leukemia cells in culture with the inhibition of dihydrofolate reductase from leukemia cells and other cell types.,  25  (2): [PMID:7057420] [10.1021/jm00344a012]

5. Selassie CD, Guo Z, Hansch C, Khwaja TA, Pentecost S..  (1982)  A comparison of the inhibition of growth of methotrexate-resistant and -sensitive leukemia cells in culture by triazines. Evidence for a new mechanism of cell resistance to methotrexate.,  25  (2): [PMID:7057421] [10.1021/jm00344a013]

6. Selassie CD, Hansch C, Khwaja TA, Dias CB, Pentecost S..  (1984)  Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate.,  27  (3): [PMID:6699880] [10.1021/jm00369a019]

Source

Source(1):

• Scientific Literature