3-(4-hydroxy-3-methoxyphenyl)-1-phenylprop-2-en-1-one

ID: ALA465025

Chembl Id: CHEMBL465025

Cas Number: 89406-16-6

PubChem CID: 6123890

Max Phase: Preclinical

Molecular Formula: C16H14O3

Molecular Weight: 254.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)c2ccccc2)ccc1O

Standard InChI:  InChI=1S/C16H14O3/c1-19-16-11-12(8-10-15(16)18)7-9-14(17)13-5-3-2-4-6-13/h2-11,18H,1H3/b9-7+

Standard InChI Key:  SFDANOZEVFTUOG-VQHVLOKHSA-N

Alternative Forms

1. Parent:

   

   ALA465025

   2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-phenyl-

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: 254.28

Molecular Weight (Monoisotopic): 254.0943

AlogP: 3.30

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: 0.40

References

1. Tatsuzaki J, Bastow KF, Nakagawa-Goto K, Nakamura S, Itokawa H, Lee KH..  (2006)  Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.,  69  (10): [PMID:17067159] [10.1021/np060252z]

2. Jung JC, Jang S, Lee Y, Min D, Lim E, Jung H, Oh M, Oh S, Jung M..  (2008)  Efficient synthesis and neuroprotective effect of substituted 1,3-diphenyl-2-propen-1-ones.,  51  (13): [PMID:18517185] [10.1021/jm800221g]

3. Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H..  (2009)  Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted.,  44  (5): [PMID:18584918] [10.1016/j.ejmech.2008.05.010]

4. Reinke AA, Seh HY, Gestwicki JE..  (2009)  A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.,  19  (17): [PMID:19640715] [10.1016/j.bmcl.2009.07.082]

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. Mokale SN, Nevase MC, Sakle NS, Dube PN, Shelke VR, Bhavale SA, Begum A..  (2014)  Synthesis and in-vivo hypolipidemic activity of some novel substituted phenyl isoxazol phenoxy acetic acid derivatives.,  24  (9): [PMID:24703232] [10.1016/j.bmcl.2014.03.030]

7. Regenass P, Abboud D, Daubeuf F, Lehalle C, Gizzi P, Riché S, Hachet-Haas M, Rohmer F, Gasparik V, Boeglin D, Haiech J, Knehans T, Rognan D, Heissler D, Marsol C, Villa P, Galzi JL, Hibert M, Frossard N, Bonnet D..  (2018)  Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia.,  61  (17): [PMID:30106292] [10.1021/acs.jmedchem.8b00657]

Source

Source(1):

• Scientific Literature