rac-2-[({5-[4-(3-Carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-yl]-5-oxopentyl}carbamoyl)-methyl]-2-hydroxybutanedioic acid

ID: ALA3313965

PubChem CID: 118707345

Max Phase: Preclinical

Molecular Formula: C28H33FN4O10

Molecular Weight: 604.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(O)(CC(=O)NCCCCC(=O)N1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1)C(=O)O

Standard InChI:  InChI=1S/C28H33FN4O10/c29-19-11-17-20(33(16-4-5-16)15-18(25(17)38)26(39)40)12-21(19)31-7-9-32(10-8-31)23(35)3-1-2-6-30-22(34)13-28(43,27(41)42)14-24(36)37/h11-12,15-16,43H,1-10,13-14H2,(H,30,34)(H,36,37)(H,39,40)(H,41,42)

Standard InChI Key:  IZABHASAPWWDJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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  4  2  1  0
  5  1  1  0
  6  1  2  0
  7  4  2  0
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 24 21  1  0
  4  3  1  0
 15 14  1  0
  8 12  2  0
 24 17  1  0
 17 25  1  0
 25 26  1  0
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 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 35 38  1  0
 38 39  2  0
 38 40  1  0
 36 41  1  0
 41 42  1  0
 41 43  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3313965

   ---

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: 604.59

Molecular Weight (Monoisotopic): 604.2181

AlogP: 0.79

#Rotatable Bonds: 13

Polar Surface Area: 206.78

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.43

CX Basic pKa: ┄

CX LogP: -0.07

CX LogD: -6.99

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.20

Np Likeness Score: -0.50

References

1. Milner SJ, Snelling AM, Kerr KG, Abd-El-Aziz A, Thomas GH, Hubbard RE, Routledge A, Duhme-Klair AK..  (2014)  Probing linker design in citric acid-ciprofloxacin conjugates.,  22  (16): [PMID:24794750] [10.1016/j.bmc.2014.04.009]

Source

Source(1):

• Scientific Literature