(N-(5-((S)-2-((3aR,5S)-5-Allyl-6-oxo-3a,4,5,6-tetrahydrobenzo[d]-[1,3]dioxol-3a-yl)propyl)-4-fluoro-2-methoxyphenyl)acetamide)

ID: ALA4556672

PubChem CID: 126509492

Max Phase: Preclinical

Molecular Formula: C22H26FNO5

Molecular Weight: 403.45

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H26FNO5/c1-5-6-15-11-22(21(10-19(15)26)28-12-29-22)13(2)7-16-8-18(24-14(3)25)20(27-4)9-17(16)23/h5,8-10,13,15H,1,6-7,11-12H2,2-4H3,(H,24,25)/t13-,15-,22+/m0/s1

Standard InChI Key:  HRGSMOAKTREXQC-LIEFOEBCSA-N

Molfile:  

 
     RDKit          2D

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   25.7303  -11.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4426  -12.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1591  -11.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4426  -10.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1579  -10.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7654  -10.2597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4333   -9.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6129   -9.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4426  -12.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0152  -12.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2941  -11.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5790  -12.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7219   -9.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7175   -9.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0080  -10.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2857   -9.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2858   -9.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5731   -8.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8536   -9.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8620   -9.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5798  -10.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1386   -8.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5853  -11.2286    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -9.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5732   -7.9286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2862   -7.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2863   -6.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9993   -7.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
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  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
 26 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556672

   ---

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: 403.45

Molecular Weight (Monoisotopic): 403.1795

AlogP: 3.76

#Rotatable Bonds: 7

Polar Surface Area: 73.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.74

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: 0.46

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