3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one

ID: ALA4464764

PubChem CID: 688803

Max Phase: Preclinical

Molecular Formula: C15H10O5

Molecular Weight: 270.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c(O)c(-c2cccc(O)c2)oc2ccc(O)cc12

Standard InChI:  InChI=1S/C15H10O5/c16-9-3-1-2-8(6-9)15-14(19)13(18)11-7-10(17)4-5-12(11)20-15/h1-7,16-17,19H

Standard InChI Key:  LRMWPUURCIXKOC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    8.2654   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2643   -3.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9723   -3.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9705   -1.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -2.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6825   -3.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949   -3.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1085   -3.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1051   -2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3881   -1.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3837   -1.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8115   -1.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8148   -3.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8157   -4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5237   -4.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2313   -4.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2264   -3.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5179   -3.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9316   -3.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5576   -1.9482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  8 13  1  0
 17 19  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464764

   3,6,3'-Trihydroxyflavone

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 270.24

Molecular Weight (Monoisotopic): 270.0528

AlogP: 2.58

#Rotatable Bonds: 1

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.48

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: 1.01

References

1. Borsari C, Luciani R, Pozzi C, Poehner I, Henrich S, Trande M, Cordeiro-da-Silva A, Santarem N, Baptista C, Tait A, Di Pisa F, Dello Iacono L, Landi G, Gul S, Wolf M, Kuzikov M, Ellinger B, Reinshagen J, Witt G, Gribbon P, Kohler M, Keminer O, Behrens B, Costantino L, Tejera Nevado P, Bifeld E, Eick J, Clos J, Torrado J, Jiménez-Antón MD, Corral MJ, Alunda JM, Pellati F, Wade RC, Ferrari S, Mangani S, Costi MP..  (2016)  Profiling of Flavonol Derivatives for the Development of Antitrypanosomatidic Drugs.,  59  (16): [PMID:27411733] [10.1021/acs.jmedchem.6b00698]

Source

Source(1):

• Scientific Literature