18-Oxoferruginol

ID: ALA1277662

Chembl Id: CHEMBL1277662

PubChem CID: 52946772

Max Phase: Preclinical

Molecular Formula: C20H28O2

Molecular Weight: 300.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 18-Oxoferruginol | 18-Oxoferruginol|CHEMBL1277662|BDBM50465345

Canonical SMILES:  CC(C)c1cc2c(cc1O)[C@@]1(C)CCC[C@@](C)(C=O)[C@@H]1CC2

Standard InChI:  InChI=1S/C20H28O2/c1-13(2)15-10-14-6-7-18-19(3,12-21)8-5-9-20(18,4)16(14)11-17(15)22/h10-13,18,22H,5-9H2,1-4H3/t18-,19-,20+/m0/s1

Standard InChI Key:  BYISLTMARMJFNI-SLFFLAALSA-N

Alternative Forms

1. Parent:

   

   ALA1277662

   18-OXOFERRUGINOL

Molecule Features

Natural Product: Yes

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: 300.44

Molecular Weight (Monoisotopic): 300.2089

AlogP: 4.72

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: 2.50

References

1. Ryu YB, Jeong HJ, Kim JH, Kim YM, Park JY, Kim D, Nguyen TT, Park SJ, Chang JS, Park KH, Rho MC, Lee WS..  (2010)  Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition.,  18  (22): [PMID:20934345] [10.1016/j.bmc.2010.09.035]

2. González MA, Clark J, Connelly M, Rivas F..  (2014)  Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group.,  24  (22): [PMID:25316317] [10.1016/j.bmcl.2014.09.061]

3. Roa-Linares VC, Brand YM, Agudelo-Gomez LS, Tangarife-Castaño V, Betancur-Galvis LA, Gallego-Gomez JC, González MA..  (2016)  Anti-herpetic and anti-dengue activity of abietane ferruginol analogues synthesized from (+)-dehydroabietylamine.,  108  [PMID:26638041] [10.1016/j.ejmech.2015.11.009]

4. Gao JB, Yang SJ, Yan ZR, Zhang XJ, Pu DB, Wang LX, Li XL, Zhang RH, Xiao WL..  (2018)  Isolation, Characterization, and Structure-Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors.,  81  (4): [PMID:29578342] [10.1021/acs.jnatprod.7b01082]

5. Martín-Escolano R,Guardia JJ,Martín-Escolano J,Cirauqui N,Fernández A,Rosales MJ,Chahboun R,Sánchez-Moreno M,Alvarez-Manzaneda E,Marín C.  (2020)  In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis.,  83  (12): [PMID:33253573] [10.1021/acs.jnatprod.0c00651]

Source

Source(1):

• Scientific Literature