(4bR,8aS)-2-Isopropyl-8,8-dimethyl-5,6,7,8,8a,9-hexahydro-3H-9,4b-(epoxymethano)phenanthrene-3,4,10,12-tetraone

ID: ALA4550442

PubChem CID: 155555314

Max Phase: Preclinical

Molecular Formula: C20H22O5

Molecular Weight: 342.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C1=CC2=C(C(=O)C1=O)[C@@]13CCCC(C)(C)[C@@H]1C(OC3=O)C2=O

Standard InChI:  InChI=1S/C20H22O5/c1-9(2)10-8-11-12(15(23)13(10)21)20-7-5-6-19(3,4)17(20)16(14(11)22)25-18(20)24/h8-9,16-17H,5-7H2,1-4H3/t16?,17-,20-/m0/s1

Standard InChI Key:  WXHCWOOFKNPNJE-IZVBFETMSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.9653  -14.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9574  -15.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6652  -14.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3691  -15.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6652  -14.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3730  -13.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3700  -12.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -12.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7820  -12.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -11.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6660  -12.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6660  -11.6549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9582  -12.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7461  -12.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9574  -13.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2496  -14.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4617  -13.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3833  -12.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2496  -14.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4617  -15.7039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5460  -15.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9525  -16.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1373  -16.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8383  -14.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8383  -14.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5460  -13.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 15 13  1  0
 16 15  1  0
 16 17  1  1
 17  1  1  0
 17 18  2  0
 19 16  1  0
 19 20  1  6
 19  2  1  0
 21 19  1  0
 21 22  1  0
 21 23  1  0
 24 21  1  0
 25 24  1  0
 25 26  1  0
 16 26  1  0
  5 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550442

   ---

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: 342.39

Molecular Weight (Monoisotopic): 342.1467

AlogP: 2.34

#Rotatable Bonds: 1

Polar Surface Area: 77.51

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: 2.43

References

1. Han S, Li X, Xia Y, Yu Z, Cai N, Malwal SR, Han X, Oldfield E, Zhang Y..  (2019)  Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells.,  62  (23): [PMID:31725297] [10.1021/acs.jmedchem.9b01405]

Source

Source(1):

• Scientific Literature