ID: ALA179374

Max Phase: Preclinical

Molecular Formula: C16H15FO2

Molecular Weight: 258.29

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(/C=C/c2ccc(F)cc2)cc(OC)c1

Standard InChI:  InChI=1S/C16H15FO2/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11H,1-2H3/b4-3+

Standard InChI Key:  BXIQOACOSDGVBH-ONEGZZNKSA-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: 258.29

Molecular Weight (Monoisotopic): 258.1056

AlogP: 4.01

#Rotatable Bonds: 4

Polar Surface Area: 18.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.77

Np Likeness Score: -0.37

References

1. de Medina P, Casper R, Savouret JF, Poirot M..  (2005)  Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators.,  48  (1): [PMID:15634023] [10.1021/jm0498194]

2. Kang SS, Cuendet M, Endringer DC, Croy VL, Pezzuto JM, Lipton MA..  (2009)  Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB.,  17  (3): [PMID:18487053] [10.1016/j.bmc.2008.04.031]

3. Moran BW, Anderson FP, Devery A, Cloonan S, Butler WE, Varughese S, Draper SM, Kenny PT..  (2009)  Synthesis, structural characterisation and biological evaluation of fluorinated analogues of resveratrol.,  17  (13): [PMID:19481462] [10.1016/j.bmc.2009.05.007]

4. Sun B, Hoshino J, Jermihov K, Marler L, Pezzuto JM, Mesecar AD, Cushman M..  (2010)  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer.,  18  (14): [PMID:20558073] [10.1016/j.bmc.2010.05.042]

5. Paul S, Mizuno CS, Lee HJ, Zheng X, Chajkowisk S, Rimoldi JM, Conney A, Suh N, Rimando AM..  (2010)  In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer.,  45  (9): [PMID:20627379] [10.1016/j.ejmech.2010.05.019]

6. Lee I, Choe YS, Choi JY, Lee KH, Kim BT..  (2012)  Synthesis and evaluation of ¹⁸F-labeled styryltriazole and resveratrol derivatives for β-amyloid plaque imaging.,  55  (2): [PMID:22236086] [10.1021/jm201400q]

7. Tripathi T, Saxena AK.  (2008)  2D- QSAR studies on new stilbene derivatives of resveratrol as a new selective aryl hydrocarbon receptor,  17  (2): [10.1007/s00044-007-9055-2]

8. St John SE, Jensen KC, Kang S, Chen Y, Calamini B, Mesecar AD, Lipton MA..  (2013)  Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2.,  21  (19): [PMID:23953689] [10.1016/j.bmc.2013.07.037]

9. Uzura S, Sekine-Suzuki E, Nakanishi I, Sonoda M, Tanimori S..  (2016)  A facile and rapid access to resveratrol derivatives and their radioprotective activity.,  26  (16): [PMID:27426305] [10.1016/j.bmcl.2016.07.018]

Source

Source(1):

• Scientific Literature