ID: ALA341135

Max Phase: Preclinical

Molecular Formula: C15H12O4

Molecular Weight: 256.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)c1ccc(O)cc1

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

Standard InChI Key:  UPERCWWUZZKHCL-LREOWRDNSA-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: 7.84

CX Basic pKa:

CX LogP: 2.98

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.45

Np Likeness Score: 0.70

References

1. Sogawa S, Nihro Y, Ueda H, Izumi A, Miki T, Matsumoto H, Satoh T..  (1993)  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.,  36  (24): [PMID:8254620] [10.1021/jm00076a019]

2. Artico M, Di Santo R, Costi R, Novellino E, Greco G, Massa S, Tramontano E, Marongiu ME, De Montis A, La Colla P..  (1998)  Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.,  41  (21): [PMID:9767632] [10.1021/jm9707232]

3. Buolamwini JK, Assefa H..  (2002)  CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.,  45  (4): [PMID:11831895] [10.1021/jm010399h]

4. Fioravanti R, Celestino I, Costi R, Cuzzucoli Crucitti G, Pescatori L, Mattiello L, Novellino E, Checconi P, Palamara AT, Nencioni L, Di Santo R..  (2012)  Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action.,  20  (16): [PMID:22743086] [10.1016/j.bmc.2012.05.062]

5. Sharma MC.  (2013)  Molecular modeling studies of substituted 3,4-dihydroxychalcone derivatives as 5-lipoxygenase and cyclooxygenase inhibitors,  [10.1007/s00044-013-0745-7]

6. 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]

Source

Source(1):

• Scientific Literature