ID: ALA2179277

Max Phase: Preclinical

Molecular Formula: C29H34BrN3O5

Molecular Weight: 584.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cn([C@H]2CCCN([C@H](CC(C)(C)C)c3ccc(C(=O)O)c(Oc4cccc(Br)c4)c3)C2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C29H34BrN3O5/c1-18-16-33(28(37)31-26(18)34)21-8-6-12-32(17-21)24(15-29(2,3)4)19-10-11-23(27(35)36)25(13-19)38-22-9-5-7-20(30)14-22/h5,7,9-11,13-14,16,21,24H,6,8,12,15,17H2,1-4H3,(H,35,36)(H,31,34,37)/t21-,24+/m0/s1

Standard InChI Key:  SXYGLXXKMZTVNB-XUZZJYLKSA-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: 584.51

Molecular Weight (Monoisotopic): 583.1682

AlogP: 5.91

#Rotatable Bonds: 7

Polar Surface Area: 104.63

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.24

CX Basic pKa: 8.92

CX LogP: 3.14

CX LogD: 3.13

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.36

Np Likeness Score: -0.68

References

1. Martínez-Botella G, Breen JN, Duffy JE, Dumas J, Geng B, Gowers IK, Green OM, Guler S, Hentemann MF, Hernandez-Juan FA, Joseph-McCarthy D, Kawatkar S, Larsen NA, Lazari O, Loch JT, Macritchie JA, McKenzie AR, Newman JV, Olivier NB, Otterson LG, Owens AP, Read J, Sheppard DW, Keating TA..  (2012)  Discovery of selective and potent inhibitors of gram-positive bacterial thymidylate kinase (TMK).,  55  (22): [PMID:23043329] [10.1021/jm3011806]

2. Kawatkar SP, Keating TA, Olivier NB, Breen JN, Green OM, Guler SY, Hentemann MF, Loch JT, McKenzie AR, Newman JV, Otterson LG, Martínez-Botella G..  (2014)  Antibacterial inhibitors of Gram-positive thymidylate kinase: structure-activity relationships and chiral preference of a new hydrophobic binding region.,  57  (11): [PMID:24828090] [10.1021/jm500463c]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data