5-(2,4-Bis-fluoromethyl-8-methoxy-2-methyl-1,2-dihydro-quinolin-6-ylmethyl)-pyrimidine-2,4-diamine

ID: ALA58149

Chembl Id: CHEMBL58149

PubChem CID: 44301099

Max Phase: Preclinical

Molecular Formula: C18H21F2N5O

Molecular Weight: 361.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc2c1NC(C)(CF)C=C2CF

Standard InChI:  InChI=1S/C18H21F2N5O/c1-18(9-20)6-12(7-19)13-4-10(5-14(26-2)15(13)25-18)3-11-8-23-17(22)24-16(11)21/h4-6,8,25H,3,7,9H2,1-2H3,(H4,21,22,23,24)

Standard InChI Key:  XGIOTZBUWCNJCW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA58149

   5-[[2,4-bis(fluoromethyl)-8-methoxy-2-methyl-1H-quinolin-6-yl]methyl]pyrimidine-2,4-diamine

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

Calculated Properties

Molecular Weight: 361.40

Molecular Weight (Monoisotopic): 361.1714

AlogP: 2.75

#Rotatable Bonds: 5

Polar Surface Area: 99.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.16

CX LogP: 1.88

CX LogD: 1.70

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: 0.27

References

1. Johnson JV, Rauchman BS, Baccanari DP, Roth B..  (1989)  2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 12. 1,2-Dihydroquinolylmethyl analogues with high activity and specificity for bacterial dihydrofolate reductase.,  32  (8): [PMID:2666668] [10.1021/jm00128a042]

Source

Source(1):

• Scientific Literature