7-((R)-2-((R,E)-4,4-difluoro-3-hydroxy-4-phenylbut-1-enyl)-5-oxopyrrolidin-1-yl)heptanoic acid

ID: ALA1956372

PubChem CID: 10272021

Max Phase: Preclinical

Molecular Formula: C21H27F2NO4

Molecular Weight: 395.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCCCCCN1C(=O)CC[C@@H]1/C=C/[C@@H](O)C(F)(F)c1ccccc1

Standard InChI:  InChI=1S/C21H27F2NO4/c22-21(23,16-8-4-3-5-9-16)18(25)13-11-17-12-14-19(26)24(17)15-7-2-1-6-10-20(27)28/h3-5,8-9,11,13,17-18,25H,1-2,6-7,10,12,14-15H2,(H,27,28)/b13-11+/t17-,18+/m0/s1

Standard InChI Key:  HWLGHEIVNKULQQ-SLKVGHROSA-N

Molfile:  

     RDKit          2D

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   -0.5877    0.2775    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167    0.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5933    0.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1077    0.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6532   -0.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8577   -0.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8128    1.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426   -0.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -0.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136   -0.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -1.6815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848   -1.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -2.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4254   -0.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3877    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6733    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1846    1.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702    2.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  6
  6  7  1  0
  2 15  1  0
  7  8  1  0
 15 16  2  0
  8  9  1  0
 16 17  1  0
  9  4  1  0
 17 18  2  0
  4  6  1  0
 18 19  1  0
  6 10  2  0
 19 20  2  0
 20 15  1  0
  3  2  1  0
  5 21  1  0
  9 11  1  1
 21 22  1  0
 22 23  1  0
 11 12  2  0
 23 24  1  0
  2  1  1  0
 24 25  1  0
 12 13  1  0
 25 26  1  0
 13  2  1  0
 26 27  1  0
  4  5  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956372

   7-{(2R)-2-[(1E,3R)-4,4-difluoro-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}heptanoic Acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 395.45

Molecular Weight (Monoisotopic): 395.1908

AlogP: 3.72

#Rotatable Bonds: 11

Polar Surface Area: 77.84

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.29

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 0.39

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: 0.09

References

1. Arns S, Gibe R, Moreau A, Monzur Morshed M, Young RN..  (2012)  Design and synthesis of novel bone-targeting dual-action pro-drugs for the treatment and reversal of osteoporosis.,  20  (6): [PMID:22341574] [10.1016/j.bmc.2012.01.024]

Source

Source(1):

• Scientific Literature