ID: ALA242199

Max Phase: Preclinical

Molecular Formula: C27H27ClN6O4

Molecular Weight: 535.00

Molecule Type: Small molecule

Representations

Synonyms (1): AR-709
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(Cc2cnc(N)nc2N)c2cc(Cc3c(C(=O)N(C)C)[nH]c4ccc(Cl)cc34)oc2c1OC

Standard InChI:  InChI=1S/C27H27ClN6O4/c1-34(2)26(35)22-19(18-9-15(28)5-6-20(18)32-22)11-16-10-17-13(7-14-12-31-27(30)33-25(14)29)8-21(36-3)24(37-4)23(17)38-16/h5-6,8-10,12,32H,7,11H2,1-4H3,(H4,29,30,31,33)

Standard InChI Key:  ASSNCSVJAZEMQG-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: 535.00

Molecular Weight (Monoisotopic): 534.1782

AlogP: 4.42

#Rotatable Bonds: 7

Polar Surface Area: 145.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 8.15

CX LogP: 3.38

CX LogD: 3.19

Aromatic Rings: 5

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: -0.27

References

1. Bennett BC, Xu H, Simmerman RF, Lee RE, Dealwis CG..  (2007)  Crystal structure of the anthrax drug target, Bacillus anthracis dihydrofolate reductase.,  50  (18): [PMID:17696333] [10.1021/jm070319v]

2. Ressner RA, Moore MR, Jorgensen JH..  (2008)  Activity of the Diaminopyrimidine AR-709 against recently collected multidrug-resistant isolates of invasive Streptococcus pneumoniae from North America.,  52  (3): [PMID:18180346] [10.1128/aac.01387-07]

3. Smith K, Ednie LM, Appelbaum PC, Hawser S, Lociuro S..  (2008)  Antistreptococcal activity of AR-709 compared to that of other agents.,  52  (6): [PMID:18362189] [10.1128/aac.01620-07]

4. Jansen WT, Verel A, Verhoef J, Milatovic D..  (2008)  In vitro activity of AR-709 against Streptococcus pneumoniae.,  52  (3): [PMID:18180358] [10.1128/aac.01332-07]

Source

Source(1):

• Scientific Literature