7-{4-[(6R,7R)-2-Carboxy-7-((R)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-piperazin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

ID: ALA134016

Chembl Id: CHEMBL134016

PubChem CID: 10394776

Max Phase: Preclinical

Molecular Formula: C33H32FN5O8S

Molecular Weight: 677.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1=C(CN2CCN(c3cc4c(cc3F)c(=O)c(C(=O)O)cn4C3CC3)CC2)CS[C@@H]2[C@H](NC(=O)[C@H](O)c3ccccc3)C(=O)N12

Standard InChI:  InChI=1S/C33H32FN5O8S/c34-22-12-20-23(38(19-6-7-19)15-21(28(20)41)32(44)45)13-24(22)37-10-8-36(9-11-37)14-18-16-48-31-25(30(43)39(31)26(18)33(46)47)35-29(42)27(40)17-4-2-1-3-5-17/h1-5,12-13,15,19,25,27,31,40H,6-11,14,16H2,(H,35,42)(H,44,45)(H,46,47)/t25-,27-,31-/m1/s1

Standard InChI Key:  CMIOGCSQKHQMAE-LMGPPYNSSA-N

Alternative Forms

1. Parent:

   

   ALA134016

   (6R,7R)-3-[[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxoquinolin-7-yl)piperazin-1-yl]methyl]-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-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: 677.71

Molecular Weight (Monoisotopic): 677.1956

AlogP: 1.77

#Rotatable Bonds: 9

Polar Surface Area: 172.72

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.00

CX Basic pKa: 6.25

CX LogP: -1.19

CX LogD: -3.79

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.24

Np Likeness Score: -0.49

References

1. Albrecht HA, Beskid G, Christenson JG, Deitcher KH, Georgopapadakou NH, Keith DD, Konzelmann FM, Pruess DL, Wei CC..  (1994)  Dual-action cephalosporins incorporating a 3'-tertiary-amine-linked quinolone.,  37  (3): [PMID:8308866] [10.1021/jm00029a012]

Source

Source(1):

• Scientific Literature