(4bS,8R,8aR)-8-Hydroxymethyl-2-isopropyl-4b,8-dimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol

ID: ALA197310

Chembl Id: CHEMBL197310

PubChem CID: 21582568

Max Phase: Preclinical

Molecular Formula: C20H30O2

Molecular Weight: 302.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 18-Hydroxyferruginol | 18-Hydroxyferruginol|CHEMBL197310|BDBM50483051

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

Standard InChI:  InChI=1S/C20H30O2/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/h10-11,13,18,21-22H,5-9,12H2,1-4H3/t18-,19-,20+/m0/s1

Standard InChI Key:  ZSMYLYMVTJVQIR-SLFFLAALSA-N

Alternative Forms

1. Parent:

   

   ALA197310

   18-HYDROXYFERRUGINOL

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: 302.46

Molecular Weight (Monoisotopic): 302.2246

AlogP: 4.52

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.80

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.84

Np Likeness Score: 2.42

References

1. Son KH, Oh HM, Choi SK, Han DC, Kwon BM..  (2005)  Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens.,  15  (8): [PMID:15808460] [10.1016/j.bmcl.2005.02.057]

2. 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]

3. Hamulić D, Stadler M, Hering S, Padrón JM, Padrón JM, Bassett R, Rivas F, Loza-Mejía MA, Dea-Ayuela MA, González-Cardenete MA..  (2019)  Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies.,  82  (4): [PMID:30840453] [10.1021/acs.jnatprod.8b00884]

4. González-Cardenete MA, Hamulić D, Miquel-Leal FJ, González-Zapata N, Jimenez-Jarava OJ, Brand YM, Restrepo-Mendez LC, Martinez-Gutierrez M, Betancur-Galvis LA, Marín ML..  (2022)  Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids.,  85  (8.0): [PMID:35969814] [10.1021/acs.jnatprod.2c00464]

Source

Source(1):

• Scientific Literature