methyl (1S,4aS,10aR)-6-hydroxy-7-isopropyl-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate

ID: ALA5193407

PubChem CID: 168289184

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C)CCC[C@]2(C)c3cc(O)c(C(C)C)cc3C(=O)C[C@@H]12

Standard InChI:  InChI=1S/C21H28O4/c1-12(2)13-9-14-15(10-16(13)22)20(3)7-6-8-21(4,19(24)25-5)18(20)11-17(14)23/h9-10,12,18,22H,6-8,11H2,1-5H3/t18-,20-,21+/m1/s1

Standard InChI Key:  WNOQMNFOGUEAIQ-NRSPTQNISA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
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   -1.3172    0.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028    0.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -0.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    0.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260    0.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -0.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121    1.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    1.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    2.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678    1.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028    0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -1.5552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7299   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551   -1.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266    2.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5407   -1.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3172   -2.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678   -2.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  3  1  0
  5  4  1  0
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  8  7  2  0
  9  8  1  0
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  8 14  1  0
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  3 18  1  1
  4 19  1  6
  5 20  1  0
  5 21  1  6
 20 22  1  0
 12 23  1  0
  9 24  2  0
 20 25  2  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5193407

   ---

Molecule Features

Natural Product: No

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: 344.45

Molecular Weight (Monoisotopic): 344.1988

AlogP: 4.34

#Rotatable Bonds: 2

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.19

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.38

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 2.26

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