ID: ALA1083821

Max Phase: Preclinical

Molecular Formula: C15H12O4

Molecular Weight: 256.26

Molecule Type: Small molecule

Representations

Synonyms (1): (E)-3,2',4'-Trihydroxychalcone
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(/C=C/c1cccc(O)c1)c1ccc(O)cc1O

Standard InChI:  InChI=1S/C15H12O4/c16-11-3-1-2-10(8-11)4-7-14(18)13-6-5-12(17)9-15(13)19/h1-9,16-17,19H/b7-4+

Standard InChI Key:  WKMQGQZPDSFACZ-QPJJXVBHSA-N

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

Properties

Molecular Weight: 256.26

Molecular Weight (Monoisotopic): 256.0736

AlogP: 2.70

#Rotatable Bonds: 3

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.11

CX Basic pKa:

CX LogP: 3.63

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.58

Np Likeness Score: 0.67

References

1. Mativandlela SP, Muthivhi T, Kikuchi H, Oshima Y, Hamilton C, Hussein AA, van der Walt ML, Houghton PJ, Lall N..  (2009)  Antimycobacterial flavonoids from the leaf extract of Galenia africana.,  72  (12): [PMID:20035557] [10.1021/np800778b]

2. Hofmann E, Webster J, Do T, Kline R, Snider L, Hauser Q, Higginbottom G, Campbell A, Ma L, Paula S..  (2016)  Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers.,  24  (4): [PMID:26762836] [10.1016/j.bmc.2015.12.024]

3. Xie Z, Luo X, Zou Z, Zhang X, Huang F, Li R, Liao S, Liu Y..  (2017)  Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia.,  27  (15): [PMID:28655421] [10.1016/j.bmcl.2017.01.053]

4. Cai CY, Rao L, Rao Y, Guo JX, Xiao ZZ, Cao JY, Huang ZS, Wang B..  (2017)  Analogues of xanthones--Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates.,  130  [PMID:28242551] [10.1016/j.ejmech.2017.02.007]

5. Selvaraj B, Kim DW, Huh G, Lee H, Kang K, Lee JW..  (2020)  Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells.,  30  (8): [PMID:32122738] [10.1016/j.bmcl.2020.127058]

Source

Source(1):

• Scientific Literature