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

ID: ALA3313964

PubChem CID: 118707344

Max Phase: Preclinical

Molecular Formula: C25H27FN4O10

Molecular Weight: 562.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H27FN4O10/c26-16-7-14-17(30(13-1-2-13)12-15(22(14)35)23(36)37)8-18(16)28-3-5-29(6-4-28)20(32)11-27-19(31)9-25(40,24(38)39)10-21(33)34/h7-8,12-13,40H,1-6,9-11H2,(H,27,31)(H,33,34)(H,36,37)(H,38,39)

Standard InChI Key:  VYUWJZXPMMZVKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.9232   -6.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6252   -4.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3483   -6.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2073   -6.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4982   -6.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6420   -7.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1877   -4.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0503   -4.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4884   -5.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7760   -5.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6660   -7.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9464   -7.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6764   -8.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2370   -7.7426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175   -7.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5071   -6.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081   -7.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -7.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -7.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596   -7.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -6.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875   -6.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -6.1284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0837   -8.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6492   -6.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -7.7962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  5  1  0
  4  2  1  0
  5  1  1  0
  6  1  2  0
  7  4  2  0
  8  7  1  0
  9  2  1  0
 10  3  2  0
 11  1  1  0
 12 10  1  0
 13  8  1  0
 14  9  1  0
 15  9  1  0
 16  5  2  0
 17 23  1  0
 18 11  2  0
 19 12  1  0
 20 11  1  0
 21 13  1  0
 22 13  1  0
 23 22  1  0
 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
 25 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 35 37  1  0
 32 38  1  0
 34 39  2  0
 34 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3313964

   ---

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: 562.51

Molecular Weight (Monoisotopic): 562.1711

AlogP: -0.38

#Rotatable Bonds: 10

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: 3.13

CX Basic pKa: ┄

CX LogP: -1.04

CX LogD: -8.38

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.25

Np Likeness Score: -0.61

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