ID: ALA139551

Max Phase: Preclinical

Molecular Formula: C21H20N4O7

Molecular Weight: 440.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(O)c2cc(COc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C21H20N4O7/c22-21-24-15-6-1-11(9-14(15)19(29)25-21)10-32-13-4-2-12(3-5-13)18(28)23-16(20(30)31)7-8-17(26)27/h1-6,9,16H,7-8,10H2,(H,23,28)(H,26,27)(H,30,31)(H3,22,24,25,29)

Standard InChI Key:  MNMMLPGKBNWPGY-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: 440.41

Molecular Weight (Monoisotopic): 440.1332

AlogP: 1.54

#Rotatable Bonds: 9

Polar Surface Area: 184.96

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.04

CX Basic pKa: 2.60

CX LogP: 1.37

CX LogD: -4.81

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -0.50

References

1. Patil SA, Shane B, Freisheim JH, Singh SK, Hynes JB..  (1989)  Inhibition of mammalian folylpolyglutamate synthetase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin bearing a terminal L-ornithine.,  32  (7): [PMID:2738891] [10.1021/jm00127a026]

2. Hynes JB, Patil SA, Tomazic A, Kumar A, Pathak A, Tan XH, Li XQ, Ratnam M, Delcamp TJ, Freisheim JH..  (1988)  Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.,  31  (2): [PMID:3339615] [10.1021/jm00397a031]

3. Hynes JB, Patil SA, Hagan RL, Cole A, Kohler W, Freisheim JH..  (1989)  Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts.,  32  (4): [PMID:2704031] [10.1021/jm00124a019]

4. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N..  (2006)  Discovery of small molecule integrin alphavbeta3 antagonists as novel anticancer agents.,  49  (15): [PMID:16854058] [10.1021/jm051296s]

5. 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

Source(1):

• Scientific Literature