ID: ALA223256

Max Phase: Preclinical

Molecular Formula: C25H28O6

Molecular Weight: 424.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cc1c(O)cc2c(c1O)C(=O)C[C@@H](c1ccc(O)c(O)c1)O2

Standard InChI:  InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)7-9-17-19(27)12-23-24(25(17)30)21(29)13-22(31-23)16-8-10-18(26)20(28)11-16/h5,7-8,10-12,22,26-28,30H,4,6,9,13H2,1-3H3/b15-7+/t22-/m0/s1

Standard InChI Key:  XCYSQFHYFNWYFP-CEMXSPGASA-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: 424.49

Molecular Weight (Monoisotopic): 424.1886

AlogP: 5.45

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.67

CX Basic pKa:

CX LogP: 5.92

CX LogD: 5.73

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: 2.31

References

1. Yoder BJ, Cao S, Norris A, Miller JS, Ratovoson F, Razafitsalama J, Andriantsiferana R, Rasamison VE, Kingston DG..  (2007)  Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.,  70  (3): [PMID:17326683] [10.1021/np060484y]

2. Smejkal K, Grycová L, Marek R, Lemière F, Jankovská D, Forejtníková H, Vanco J, Suchý V..  (2007)  C-geranyl compounds from Paulownia tomentosa fruits.,  70  (8): [PMID:17625893] [10.1021/np070063w]

3. Smejkal K, Chudík S, Kloucek P, Marek R, Cvacka J, Urbanová M, Julínek O, Kokoska L, Slapetová T, Holubová P, Zima A, Dvorská M..  (2008)  Antibacterial C-geranylflavonoids from Paulownia tomentosa Fruits.,  71  (4): [PMID:18293924] [10.1021/np070446u]

4. Murphy BT, Cao S, Norris A, Miller JS, Ratovoson F, Andriantsiferana R, Rasamison VE, Kingston DG..  (2005)  Cytotoxic flavanones of Schizolaena hystrix from the Madagascar rainforest.,  68  (3): [PMID:15787448] [10.1021/np049639x]

5. Phommart S, Sutthivaiyakit P, Chimnoi N, Ruchirawat S, Sutthivaiyakit S..  (2005)  Constituents of the leaves of Macaranga tanarius.,  68  (6): [PMID:15974621] [10.1021/np0500272]

6. Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall'acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K..  (2010)  Cytotoxic activities of several geranyl-substituted flavanones.,  73  (4): [PMID:20192247] [10.1021/np900681y]

7. Cho JK, Ryu YB, Curtis-Long MJ, Ryu HW, Yuk HJ, Kim DW, Kim HJ, Lee WS, Park KH..  (2012)  Cholinestrase inhibitory effects of geranylated flavonoids from Paulownia tomentosa fruits.,  20  (8): [PMID:22445674] [10.1016/j.bmc.2012.02.044]

8. Cho JK, Curtis-Long MJ, Lee KH, Kim DW, Ryu HW, Yuk HJ, Park KH..  (2013)  Geranylated flavonoids displaying SARS-CoV papain-like protease inhibition from the fruits of Paulownia tomentosa.,  21  (11): [PMID:23623680] [10.1016/j.bmc.2013.03.027]

9. Hošek J, Toniolo A, Neuwirth O, Bolego C..  (2013)  Prenylated and geranylated flavonoids increase production of reactive oxygen species in mouse macrophages but inhibit the inflammatory response.,  76  (9): [PMID:23947936] [10.1021/np400242e]

10. Hanáková Z, Hošek J, Babula P, Dall'Acqua S, Václavík J, Šmejkal K..  (2015)  C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-α Production.,  78  (4): [PMID:25735399] [10.1021/acs.jnatprod.5b00005]

11. Ryu HW, Park YJ, Lee SU, Lee S, Yuk HJ, Seo KH, Kim YU, Hwang BY, Oh SR..  (2017)  Potential Anti-inflammatory Effects of the Fruits of Paulownia tomentosa.,  80  (10): [PMID:28968119] [10.1021/acs.jnatprod.7b00325]

12. Hanáková Z, Hošek J, Kutil Z, Temml V, Landa P, Vaněk T, Schuster D, Dall'Acqua S, Cvačka J, Polanský O, Šmejkal K..  (2017)  Anti-inflammatory Activity of Natural Geranylated Flavonoids: Cyclooxygenase and Lipoxygenase Inhibitory Properties and Proteomic Analysis.,  80  (4): [PMID:28322565] [10.1021/acs.jnatprod.6b01011]

13. Maruta H, Ahn MR..  (2017)  From bench (laboratory) to bed (hospital/home): How to explore effective natural and synthetic PAK1-blockers/longevity-promoters for cancer therapy.,  142  [PMID:28814374] [10.1016/j.ejmech.2017.07.043]

Source

Source(1):

• Scientific Literature