ID: ALA156127

Max Phase: Preclinical

Molecular Formula: C24H30O3

Molecular Weight: 366.50

Molecule Type: Small molecule

Representations

Synonyms (1): Umbelliprenin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC/C(C)=C/CC/C(C)=C/COc1ccc2ccc(=O)oc2c1

Standard InChI:  InChI=1S/C24H30O3/c1-18(2)7-5-8-19(3)9-6-10-20(4)15-16-26-22-13-11-21-12-14-24(25)27-23(21)17-22/h7,9,11-15,17H,5-6,8,10,16H2,1-4H3/b19-9+,20-15+

Standard InChI Key:  GNMUGVNEWCZUAA-WOWYBKFKSA-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: 366.50

Molecular Weight (Monoisotopic): 366.2195

AlogP: 6.59

#Rotatable Bonds: 9

Polar Surface Area: 39.44

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.31

CX LogD: 6.31

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: 1.27

References

1. Murakami A, Gao G, Omura M, Yano M, Ito C, Furukawa H, Takahashi D, Koshimizu K, Ohigashi H..  (2000)  1,1-Dimethylallylcoumarins potently suppress both lipopolysaccharide- and interferon-gamma-induced nitric oxide generation in mouse macrophage RAW 264.7 cells.,  10  (1): [PMID:10636244] [10.1016/s0960-894x(99)00578-8]

2. Cravotto G, Balliano G, Robaldo B, Oliaro-Bosso S, Chimichi S, Boccalini M..  (2004)  Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors.,  14  (8): [PMID:15050630] [10.1016/j.bmcl.2004.01.085]

3. PubChem BioAssay data set, 

4. Bruyère C, Genovese S, Lallemand B, Ionescu-Motatu A, Curini M, Kiss R, Epifano F..  (2011)  Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.,  21  (14): [PMID:21696954] [10.1016/j.bmcl.2011.05.089]

5. Iranshahi M, Jabbari A, Orafaie A, Mehri R, Zeraatkar S, Ahmadi T, Alimardani M, Sadeghian H..  (2012)  Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.,  57  [PMID:23047230] [10.1016/j.ejmech.2012.09.006]

6. Jun M, Bacay AF, Moyer J, Webb A, Carrico-Moniz D..  (2014)  Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.,  24  (19): [PMID:25205194] [10.1016/j.bmcl.2014.08.038]

7. Sangshetti JN, Khan FA, Kulkarni AA, Patil RH, Pachpinde AM, Lohar KS, Shinde DB..  (2016)  Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction.,  26  (3): [PMID:26778149] [10.1016/j.bmcl.2015.12.085]

8. Genovese S, Taddeo VA, Epifano F, Fiorito S, Bize C, Rives A, de Medina P..  (2017)  Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.,  80  (9): [PMID:28853883] [10.1021/acs.jnatprod.7b00175]

9. Hasan M, Genovese S, Fiorito S, Epifano F, Witt-Enderby PA..  (2017)  Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.,  80  (12): [PMID:29144746] [10.1021/acs.jnatprod.7b00853]

10. Fiorito S, Epifano F, Preziuso F, Cacciatore I, di Stefano A, Taddeo VA, de Medina P, Genovese S..  (2018)  Natural oxyprenylated coumarins are modulators of melanogenesis.,  152  [PMID:29730190] [10.1016/j.ejmech.2018.04.051]

11. Gonçalves GA, Spillere AR, das Neves GM, Kagami LP, von Poser GL, Canto RFS, Eifler-Lima V..  (2020)  Natural and synthetic coumarins as antileishmanial agents: A review.,  203  [PMID:32668302] [10.1016/j.ejmech.2020.112514]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays