7-(4-(((6R,7R)-2-carboxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-yl)methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA374539

Chembl Id: CHEMBL374539

Cas Number: 143983-11-3

PubChem CID: 16077303

Max Phase: Preclinical

Molecular Formula: C33H32FN5O7S

Molecular Weight: 661.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)O)=C(CN3CCN(c4cc5c(cc4F)c(=O)c(C(=O)O)cn5C4CC4)CC3)CS[C@H]12

Standard InChI:  InChI=1S/C33H32FN5O7S/c34-23-13-21-24(38(20-6-7-20)16-22(29(21)41)32(43)44)14-25(23)37-10-8-36(9-11-37)15-19-17-47-31-27(30(42)39(31)28(19)33(45)46)35-26(40)12-18-4-2-1-3-5-18/h1-5,13-14,16,20,27,31H,6-12,15,17H2,(H,35,40)(H,43,44)(H,45,46)/t27-,31-/m1/s1

Standard InChI Key:  NESALWSWEOBRLS-DLFZDVPBSA-N

Alternative Forms

1. Parent:

   

   ALA374539

   (6R,7R)-3-[[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-7-quinolyl)piperazin-1-yl]methyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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: 661.71

Molecular Weight (Monoisotopic): 661.2006

AlogP: 2.28

#Rotatable Bonds: 9

Polar Surface Area: 152.49

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.08

CX Basic pKa: 6.25

CX LogP: -0.45

CX LogD: -3.07

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.29

Np Likeness Score: -0.65

References

1. Zhao G, Miller MJ, Franzblau S, Wan B, Möllmann U..  (2006)  Syntheses and studies of quinolone-cephalosporins as potential anti-tuberculosis agents.,  16  (21): [PMID:16945530] [10.1016/j.bmcl.2006.08.045]

2. Majewski MW, Tiwari R, Miller PA, Cho S, Franzblau SG, Miller MJ..  (2016)  Design, syntheses, and anti-tuberculosis activities of conjugates of piperazino-1,3-benzothiazin-4-ones (pBTZs) with 2,7-dimethylimidazo [1,2-a]pyridine-3-carboxylic acids and 7-phenylacetyl cephalosporins.,  26  (8): [PMID:26951749] [10.1016/j.bmcl.2016.02.076]

Source

Source(1):

• Scientific Literature