(S,E)-2-[4-(3-Chloro-2-hydroxypropoxy)phenyl]-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one

ID: ALA5267608

Max Phase: Preclinical

Molecular Formula: C19H19ClO6

Molecular Weight: 378.81

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1ccc(OCC(O)CCl)cc1)CC2=O

Standard InChI:  InChI=1S/C19H19ClO6/c1-24-14-6-15(22)19-16(23)8-17(26-18(19)7-14)11-2-4-13(5-3-11)25-10-12(21)9-20/h2-7,12,17,21-22H,8-10H2,1H3/t12?,17-/m0/s1

Standard InChI Key:  WLKNZAKSWATIHH-TYJDENFWSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.4256   -2.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142   -1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -1.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8531   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8531   -2.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838    0.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982   -0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275    0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7113    1.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    1.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692    1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692    2.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9982    1.4426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  0
  7  2  1  0
  7  6  2  0
  8  7  1  0
  8  9  1  0
 10  8  2  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 14 11  2  0
  6 14  1  0
  4 15  1  6
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 20 15  2  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5267608

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.81

Molecular Weight (Monoisotopic): 378.0870

AlogP: 3.09

#Rotatable Bonds: 6

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.69

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: 1.00

References

1. Ferreira RJ, Gajdács M, Kincses A, Spengler G, Dos Santos DJVA, Ferreira MU..  (2020)  Nitrogen-containing naringenin derivatives for reversing multidrug resistance in cancer.,  28  (23.0): [PMID:33038666] [10.1016/j.bmc.2020.115798]

Source

Source(1):

• Scientific Literature