ID: ALA174839

Max Phase: Preclinical

Molecular Formula: C24H30O3

Molecular Weight: 366.50

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC(C)=CCC/C(C)=C/CC/C(C)=C/Cc1c(O)oc2ccccc2c1=O

Standard InChI:  InChI=1S/C24H30O3/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-21-23(25)20-13-5-6-14-22(20)27-24(21)26/h5-6,9,11,13-15,26H,7-8,10,12,16H2,1-4H3/b18-11+,19-15+

Standard InChI Key:  PRSOPHSUKXJKIM-CFBAGHHKSA-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: 6.46

#Rotatable Bonds: 8

Polar Surface Area: 50.44

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.71

CX Basic pKa:

CX LogP: 6.74

CX LogD: 5.04

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: 1.43

References

1. 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]

2. Gebauer M..  (2007)  Synthesis and structure-activity relationships of novel warfarin derivatives.,  15  (6): [PMID:17275317] [10.1016/j.bmc.2007.01.014]

3. Appendino G, Mercalli E, Fuzzati N, Arnoldi L, Stavri M, Gibbons S, Ballero M, Maxia A..  (2004)  Antimycobacterial coumarins from the sardinian giant fennel (Ferula communis).,  67  (12): [PMID:15620264] [10.1021/np049706n]

4. PubChem BioAssay data set, 

5. Mamoci E, Cavoski I, Andres MF, Diaz CE, Gonzalez-Coloma A.  (2012)  Chemical characterization of the aphid antifeedant extracts from Dittrichia viscosa and Ferula communis,  43  [10.1016/j.bse.2012.02.012]

6. Ahmad I, Thakur JP, Chanda D, Saikia D, Khan F, Dixit S, Kumar A, Konwar R, Negi AS, Gupta A..  (2013)  Syntheses of lipophilic chalcones and their conformationally restricted analogues as antitubercular agents.,  23  (5): [PMID:23369537] [10.1016/j.bmcl.2012.12.096]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays