ID: ALA2348794

Max Phase: Preclinical

Molecular Formula: C21H16Cl2N4O2

Molecular Weight: 427.29

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@H](Nc1cccc(Cl)c1Cl)C(=O)Nc1ccc2oc(-c3ccncc3)nc2c1

Standard InChI:  InChI=1S/C21H16Cl2N4O2/c1-12(25-16-4-2-3-15(22)19(16)23)20(28)26-14-5-6-18-17(11-14)27-21(29-18)13-7-9-24-10-8-13/h2-12,25H,1H3,(H,26,28)/t12-/m0/s1

Standard InChI Key:  IMBVKBZWLRXRAW-LBPRGKRZSA-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: 427.29

Molecular Weight (Monoisotopic): 426.0650

AlogP: 5.64

#Rotatable Bonds: 5

Polar Surface Area: 80.05

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.78

CX Basic pKa: 2.83

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.94

References

1. Gorla SK, Kavitha M, Zhang M, Chin JE, Liu X, Striepen B, Makowska-Grzyska M, Kim Y, Joachimiak A, Hedstrom L, Cuny GD..  (2013)  Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5'-monophosphate dehydrogenase.,  56  (10): [PMID:23668331] [10.1021/jm400241j]

2. Mandapati K, Gorla SK, House AL, McKenney ES, Zhang M, Rao SN, Gollapalli DR, Mann BJ, Goldberg JB, Cuny GD, Glomski IJ, Hedstrom L..  (2014)  Repurposing cryptosporidium inosine 5'-monophosphate dehydrogenase inhibitors as potential antibacterial agents.,  5  (8): [PMID:25147601] [10.1021/ml500203p]

3. Chacko S, Boshoff HIM, Singh V, Ferraris DM, Gollapalli DR, Zhang M, Lawson AP, Pepi MJ, Joachimiak A, Rizzi M, Mizrahi V, Cuny GD, Hedstrom L..  (2018)  Expanding Benzoxazole-Based Inosine 5'-Monophosphate Dehydrogenase (IMPDH) Inhibitor Structure-Activity As Potential Antituberculosis Agents.,  61  (11): [PMID:29746130] [10.1021/acs.jmedchem.7b01839]

4. Sahu NU, Singh V, Ferraris DM, Rizzi M, Kharkar PS..  (2018)  Hit discovery of Mycobacterium tuberculosis inosine 5'-monophosphate dehydrogenase, GuaB2, inhibitors.,  28  (10): [PMID:29699922] [10.1016/j.bmcl.2018.04.045]

Source

Source(1):

• Scientific Literature