3,5-Bis-[1-(3,4-dihydroxy-phenyl)-meth-(E)-ylidene]-tetrahydro-pyran-4-one

ID: ALA419981

Chembl Id: CHEMBL419981

PubChem CID: 6474889

Max Phase: Preclinical

Molecular Formula: C19H16O6

Molecular Weight: 340.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(O)c(O)c2)COC/C1=C\c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C19H16O6/c20-15-3-1-11(7-17(15)22)5-13-9-25-10-14(19(13)24)6-12-2-4-16(21)18(23)8-12/h1-8,20-23H,9-10H2/b13-5+,14-6+

Standard InChI Key:  WJXMHIODWHBGHP-ACFHMISVSA-N

Alternative Forms

1. Parent:

   

   ALA419981

   3,5-Bis((3,4-dihydroxyphenyl)methylene)oxan-4-one

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

Calculated Properties

Molecular Weight: 340.33

Molecular Weight (Monoisotopic): 340.0947

AlogP: 2.58

#Rotatable Bonds: 2

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.66

CX Basic pKa: ┄

CX LogP: 3.00

CX LogD: 2.98

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: 0.36

References

1. 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]

2. 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]

3. 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]

4. Huang L, Wang J, Chen L, Zhu M, Wu S, Chu S, Zheng Y, Fan Z, Zhang J, Li W, Chen D, Yang X, Wang S, Qiu P, Wu J..  (2018)  Design, synthesis, and evaluation of NDGA analogues as potential anti-ischemic stroke agents.,  143  [PMID:29126723] [10.1016/j.ejmech.2017.09.028]

5. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]

Source

Source(1):

• Scientific Literature