(1R,4aS,10aR)-methyl 6-hydroxy-7-isopropyl-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate

ID: ALA4549575

Chembl Id: CHEMBL4549575

PubChem CID: 102152190

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Molecule Type: Unknown

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-HMXCVIKNSA-N

Alternative Forms

1. Parent:

   

   ALA4549575

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

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

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. 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]

2. 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