2-Hydroxy-3-((E)-3-methyl-but-1-enyl)-[1,4]naphthoquinone

ID: ALA62718

Cas Number: 4042-39-1

PubChem CID: 5376552

Max Phase: Preclinical

Molecular Formula: C15H14O3

Molecular Weight: 242.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)/C=C/C1=C(O)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-9,18H,1-2H3/b8-7+

Standard InChI Key:  FHECNCZIYPTBRB-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.6625   -8.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -7.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -8.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -8.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -7.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -8.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -9.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -9.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -6.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -7.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -8.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917  -10.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917  -10.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -9.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167   -8.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7  1  1  0
  8  7  2  0
  9  3  2  0
 10  4  2  0
 11  2  1  0
 12  6  2  0
 13  5  2  0
 14  8  1  0
 15 14  1  0
 16 14  1  0
 17 18  2  0
 18 13  1  0
  4  6  1  0
 17 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA62718

   Isolapachol

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: 242.27

Molecular Weight (Monoisotopic): 242.0943

AlogP: 3.09

#Rotatable Bonds: 2

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.25

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: 1.46

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.87

Np Likeness Score: 1.04

References

1. Goulart MO, Zani CL, Tonholo J, Freitas LR, de Abreu FC, Oliveira AB, Raslan DS, Starling S, Chiari E.  (1997)  Trypanocidal activity and redox potential of heterocyclic- and 2-hydroxy-naphthoquinones,  7  (15): [10.1016/S0960-894X(97)00354-5]

2. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature