5,7-Dihydroxy-6-(3-methyl-but-2-enyl)-2-phenyl-chromen-4-one

ID: ALA163972

Chembl Id: CHEMBL163972

Cas Number: 50678-91-6

PubChem CID: 443123

Max Phase: Preclinical

Molecular Formula: C20H18O4

Molecular Weight: 322.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6-Prenylchrysin | 6-prenylchrysin|6-(3,3-DMA)chrysin|50678-91-6|6-(3,3-Dimethylallyl)chrysin|CHEBI:2161|CHEMBL163972|5,7-dihydroxy-6-(3-methylbut-2-enyl)-2-phenylchromen-4-one|C11324|4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-|AC1L9E2B|SCHEMBL20954091|DTXSID40332054|BDBM50595119|Q27105567|5,7-dihydroxy-6-(3-methylbut-2-enyl)-2-phenyl-chromen-4-one|5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-2-phenyl-4H-1-benzopyran-4-one

Canonical SMILES:  CC(C)=CCc1c(O)cc2oc(-c3ccccc3)cc(=O)c2c1O

Standard InChI:  InChI=1S/C20H18O4/c1-12(2)8-9-14-15(21)10-18-19(20(14)23)16(22)11-17(24-18)13-6-4-3-5-7-13/h3-8,10-11,21,23H,9H2,1-2H3

Standard InChI Key:  SIXNWJHCSFYZBN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA163972

   6-Prenylchrysin

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: 322.36

Molecular Weight (Monoisotopic): 322.1205

AlogP: 4.38

#Rotatable Bonds: 3

Polar Surface Area: 70.67

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.39

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 3.63

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: 1.72

References

1. Comte G, Daskiewicz JB, Bayet C, Conseil G, Viornery-Vanier A, Dumontet C, Di Pietro A, Barron D..  (2001)  C-Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance.,  44  (5): [PMID:11262086] [10.1021/jm991128y]

2. Daskiewicz JB, Depeint F, Viornery L, Bayet C, Comte-Sarrazin G, Comte G, Gee JM, Johnson IT, Ndjoko K, Hostettmann K, Barron D..  (2005)  Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study.,  48  (8): [PMID:15828817] [10.1021/jm040770b]

3. Valdameri G, Genoux-Bastide E, Peres B, Gauthier C, Guitton J, Terreux R, Winnischofer SM, Rocha ME, Boumendjel A, Di Pietro A..  (2012)  Substituted chromones as highly potent nontoxic inhibitors, specific for the breast cancer resistance protein.,  55  (2): [PMID:22165858] [10.1021/jm201404w]

4. Zattoni IF, Delabio LC, Dutra JP, Kita DH, Scheiffer G, Hembecker M, Pereira GDS, Moure VR, Valdameri G..  (2022)  Targeting breast cancer resistance protein (BCRP/ABCG2): Functional inhibitors and expression modulators.,  237  [PMID:35483322] [10.1016/j.ejmech.2022.114346]

5. Moinul M, Amin SA, Jha T, Gayen S..  (2022)  Updated chemical scaffolds of ABCG2 inhibitors and their structure-inhibition relationships for future development.,  241  [PMID:35944339] [10.1016/j.ejmech.2022.114628]

Source

Source(1):

• Scientific Literature