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

ID: ALA5171085

PubChem CID: 168270170

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H26O4/c1-11(2)12-8-13-14(9-15(12)21)19(3)6-5-7-20(4,18(23)24)17(19)10-16(13)22/h8-9,11,17,21H,5-7,10H2,1-4H3,(H,23,24)/t17-,19-,20+/m1/s1

Standard InChI Key:  GHBDGQQTWLVNLP-RLLQIKCJSA-N

Molfile:  

 
     RDKit          2D

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    0.6203    1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0468    2.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8092    0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -1.5552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -1.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -1.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    2.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -1.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -2.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3 18  1  1
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  9 24  2  0
 20 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5171085

   ---

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: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.25

#Rotatable Bonds: 2

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 4.30

CX LogD: 1.04

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: 2.36

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