(S,E)-2-(4-Oxyranphenyl)-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one

ID: ALA5275141

Max Phase: Preclinical

Molecular Formula: C19H18O6

Molecular Weight: 342.35

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1ccc(OCC3CO3)cc1)CC2=O

Standard InChI:  InChI=1S/C19H18O6/c1-22-13-6-15(20)19-16(21)8-17(25-18(19)7-13)11-2-4-12(5-3-11)23-9-14-10-24-14/h2-7,14,17,20H,8-10H2,1H3/t14?,17-/m0/s1

Standard InChI Key:  GURXROVSJOIFPP-JRZJBTRGSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.2690   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544    0.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425   -0.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425   -0.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -1.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -2.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4131   -0.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298    0.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2997    0.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2999    1.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276    1.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4422    1.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247   -2.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836    0.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6982   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    1.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    1.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982    1.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.2127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  3 11  1  0
 10 12  1  6
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
 15 18  1  0
  8 19  2  0
  1 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 24 23  1  0
 24 25  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5275141

   ---

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: 342.35

Molecular Weight (Monoisotopic): 342.1103

AlogP: 2.88

#Rotatable Bonds: 5

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.69

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: 2.95

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.84

Np Likeness Score: 1.13

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