2-Bromo-N-{4-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenoxy]-phenyl}-acetamide

ID: ALA171639

Chembl Id: CHEMBL171639

PubChem CID: 64942

Max Phase: Preclinical

Molecular Formula: C21H22BrN5O4

Molecular Weight: 488.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)cc(OC)c1Oc1ccc(NC(=O)CBr)cc1

Standard InChI:  InChI=1S/C21H22BrN5O4/c1-29-16-8-12(7-13-11-25-21(24)27-20(13)23)9-17(30-2)19(16)31-15-5-3-14(4-6-15)26-18(28)10-22/h3-6,8-9,11H,7,10H2,1-2H3,(H,26,28)(H4,23,24,25,27)

Standard InChI Key:  ORFJPZMECGXLNE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA171639

   2-bromo-N-[4-[4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenoxy]phenyl]acetamide

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: 488.34

Molecular Weight (Monoisotopic): 487.0855

AlogP: 3.37

#Rotatable Bonds: 8

Polar Surface Area: 134.61

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.15

CX LogP: 2.90

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -0.49

References

1. Roth B, Aig E, Rauckman BS, Strelitz JZ, Phillips AP, Ferone R, Bushby SR, Sigel CW..  (1981)  2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogues of trimethoprim.,  24  (8): [PMID:7035668] [10.1021/jm00140a005]

Source

Source(1):

• Scientific Literature