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

ID: ALA4539078

PubChem CID: 126509682

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)Cc3c(F)cc(OC)cc3F)OCOC2=CC1=O

Standard InChI:  InChI=1S/C20H22F2O4/c1-4-5-13-10-20(19(9-18(13)23)25-11-26-20)12(2)6-15-16(21)7-14(24-3)8-17(15)22/h4,7-9,12-13H,1,5-6,10-11H2,2-3H3/t12-,13+,20-/m1/s1

Standard InChI Key:  HNJCKARBCXNXTO-MTJIALIYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.5015   -9.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5015  -10.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2134  -10.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9294  -10.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2134   -9.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9282   -9.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5354   -9.1976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2035   -8.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837   -8.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2134  -11.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7869  -10.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0662  -10.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3516  -10.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4932   -8.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4887   -8.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798   -9.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579   -8.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580   -8.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -7.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -8.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351   -8.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -9.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121   -7.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3579  -10.1658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -8.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7706   -7.6904    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  5  1  1  6
  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  0
  3 10  2  0
  2 11  1  1
 11 12  1  0
 12 13  2  0
 14  5  1  0
 14 15  1  1
 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
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539078

   ---

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: 0.95

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