[(4aS,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanol

ID: ALA5202539

PubChem CID: 131704771

Max Phase: Preclinical

Molecular Formula: C20H30O

Molecular Weight: 286.46

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc2c(c1)CC[C@H]1C(C)(CO)CCC[C@]21C

Standard InChI:  InChI=1S/C20H30O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18,21H,5,7,9-11,13H2,1-4H3/t18-,19?,20+/m0/s1

Standard InChI Key:  WSKGRAGZAQRSED-SJBAFXMYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.2381   -0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    0.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -1.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -1.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947    0.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197   -0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197   -1.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947   -1.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942    0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    1.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321    0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371    0.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    1.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    2.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -1.9125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -2.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -2.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -2.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  7 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  8 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
  3 18  1  1
  4 19  1  6
  5 20  1  0
  5 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202539

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 286.46

Molecular Weight (Monoisotopic): 286.2297

AlogP: 4.81

#Rotatable Bonds: 2

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: 2.01

References

1. 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