(Z)-2-hydroxy-4-(4-(octyloxy)phenyl)-4-oxobut-2-enoic acid

ID: ALA2063259

Max Phase: Preclinical

Molecular Formula: C18H24O5

Molecular Weight: 320.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCOc1ccc(C(=O)/C=C(\O)C(=O)O)cc1

Standard InChI:  InChI=1S/C18H24O5/c1-2-3-4-5-6-7-12-23-15-10-8-14(9-11-15)16(19)13-17(20)18(21)22/h8-11,13,20H,2-7,12H2,1H3,(H,21,22)/b17-13-

Standard InChI Key:  LOLDLWKHRAJWHI-LGMDPLHJSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   14.8422  -14.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8420  -15.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5572  -15.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2711  -15.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2653  -14.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5495  -14.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1257  -14.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4133  -14.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6968  -14.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9844  -14.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679  -14.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5555  -14.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8389  -14.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1265  -14.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4100  -14.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9876  -15.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9918  -16.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7000  -15.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4166  -15.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1289  -15.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4208  -16.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8469  -15.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1261  -14.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  1  0
  1  7  1  0
 14 15  1  0
  3  4  2  0
  4 16  1  0
  7  8  1  0
 16 17  2  0
 16 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 19 21  1  0
  2  3  1  0
 10 11  1  0
 20 22  1  0
 20 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2063259

   ---

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: 320.38

Molecular Weight (Monoisotopic): 320.1624

AlogP: 4.14

#Rotatable Bonds: 11

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.05

CX Basic pKa: ┄

CX LogP: 4.14

CX LogD: 0.61

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.28

Np Likeness Score: 0.07

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