((6S,7aR)-6-Allyl-7a-((S)-1-(2,5-difluoro-4-methoxyphenyl)-propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one)

ID: ALA4553192

PubChem CID: 126509361

Max Phase: Preclinical

Molecular Formula: C20H22F2O4

Molecular Weight: 364.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC[C@H]1C[C@]2([C@@H](C)Cc3cc(F)c(OC)cc3F)OCOC2=CC1=O

Standard InChI:  InChI=1S/C20H22F2O4/c1-4-5-13-10-20(19(9-17(13)23)25-11-26-20)12(2)6-14-7-16(22)18(24-3)8-15(14)21/h4,7-9,12-13H,1,5-6,10-11H2,2-3H3/t12-,13-,20+/m0/s1

Standard InChI Key:  HBZILKFBVZHWIS-KQHSUYLTSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   35.5486   -4.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5486   -4.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2605   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9766   -4.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2605   -3.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9754   -4.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5826   -3.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2507   -2.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4308   -2.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2605   -6.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8339   -5.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1132   -4.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3986   -5.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5402   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5358   -2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8269   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1049   -3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1050   -2.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3926   -1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6737   -2.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6820   -3.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3994   -3.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9590   -1.9543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4048   -4.4228    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.2484   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3927   -1.1246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5  9  1  6
  3 10  2  0
  2 11  1  1
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 22 24  1  0
 23 25  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553192

   ---

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: 364.39

Molecular Weight (Monoisotopic): 364.1486

AlogP: 3.94

#Rotatable Bonds: 6

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: 0.80

References

1. Huang Z, Williams RB, Martin SM, Lawrence JA, Norman VL, O'Neil-Johnson M, Harding J, Mangette JE, Liu S, Guzzo PR, Starks CM, Eldridge GR..  (2018)  Bifidenone: Structure-Activity Relationship and Advanced Preclinical Candidate.,  61  (15): [PMID:29995409] [10.1021/acs.jmedchem.7b01644]

Source

Source(1):

• Scientific Literature