(Z)-4-((3-(3-(hexyloxy)phenyl)propyl)amino)-2-hydroxy-4-oxobut-2-enoic acid

ID: ALA2063255

Max Phase: Preclinical

Molecular Formula: C19H27NO5

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCOc1cccc(CCCNC(=O)/C=C(\O)C(=O)O)c1

Standard InChI:  InChI=1S/C19H27NO5/c1-2-3-4-5-12-25-16-10-6-8-15(13-16)9-7-11-20-18(22)14-17(21)19(23)24/h6,8,10,13-14,21H,2-5,7,9,11-12H2,1H3,(H,20,22)(H,23,24)/b17-14-

Standard InChI Key:  LTXZSLKTHFHDTP-VKAVYKQESA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   11.3839   -6.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3837   -7.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0988   -7.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8127   -7.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8070   -6.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0912   -5.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5184   -5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2359   -6.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9473   -5.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6648   -6.3371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3762   -5.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3702   -5.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0937   -6.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8051   -5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5226   -6.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7991   -5.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5307   -7.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2361   -5.9008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674   -5.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9550   -6.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2385   -5.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5261   -6.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8095   -5.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0971   -6.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -5.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 14 16  1  0
  7  8  1  0
 15 17  1  0
 15 18  2  0
  8  9  1  0
  1 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2063255

   ---

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: 349.43

Molecular Weight (Monoisotopic): 349.1889

AlogP: 3.22

#Rotatable Bonds: 12

Polar Surface Area: 95.86

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.76

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: -0.13

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.31

Np Likeness Score: -0.16

References

1. Zhang Y, Fu-Yang Lin, Li K, Zhu W, Liu YL, Cao R, Pang R, Lee E, Axelson J, Hensler M, Wang K, Molohon KJ, Wang Y, Mitchell DA, Nizet V, Oldfield E..  (2012)  HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis.,  3  (5): [PMID:22662288] [10.1021/ml300038t]

Source

Source(1):

• Scientific Literature