3,7,3'-trihydroxyflavone

ID: ALA1801015

Cas Number: 151698-64-5

PubChem CID: 5393165

Max Phase: Preclinical

Molecular Formula: C15H10O5

Molecular Weight: 270.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,7,3'-Trihydroxyflavone | 3,7,3'-TRIHYDROXYFLAVONE|151698-64-5|3',7-Dihydroxyflavonol|SCHEMBL344155|CHEMBL1801015|PSGKFXVPVUNGDT-UHFFFAOYSA-N|AKOS024283066|NS00116347|Z3243670631|4H-1-Benzopyran-4-one, 3,7-dihydroxy-2-(3-hydroxyphenyl)-

Canonical SMILES:  O=c1c(O)c(-c2cccc(O)c2)oc2cc(O)ccc12

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

Standard InChI Key:  PSGKFXVPVUNGDT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    8.9388  -17.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9376  -17.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6516  -18.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6498  -16.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3645  -17.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3679  -17.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0863  -18.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8059  -17.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8025  -17.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0795  -16.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5138  -16.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2290  -17.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9409  -16.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9388  -15.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2189  -15.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5099  -15.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0886  -19.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250  -16.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2134  -14.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5207  -18.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
  5  6  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  4  1  1  0
  7 17  2  0
  5 10  1  0
  1 18  1  0
  6  7  1  0
 15 19  1  0
  7  8  1  0
  8 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1801015

   3,7,3'-Trihydroxyflavone

Molecule Features

Natural Product: Yes

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: 270.24

Molecular Weight (Monoisotopic): 270.0528

AlogP: 2.58

#Rotatable Bonds: 1

Polar Surface Area: 90.90

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.32

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 1.02

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: 1.06

References

1. Liu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, Phun LH, France S, Xiao G, Jia Y, Luo HR, Ye K..  (2010)  A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect.,  53  (23): [PMID:21073191] [10.1021/jm101206p]

2. 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]

3. Proença C, Oliveira A, Freitas M, Ribeiro D, Sousa JLC, Ramos MJ, Silva AMS, Fernandes PA, Fernandes E..  (2020)  Structural Specificity of Flavonoids in the Inhibition of Human Fructose 1,6-Bisphosphatase.,  83  (5): [PMID:32364726] [10.1021/acs.jnatprod.0c00014]

Source

Source(1):

• Scientific Literature