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

ID: ALA1956374

PubChem CID: 57392193

Max Phase: Preclinical

Molecular Formula: C23H31F2NO4

Molecular Weight: 423.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H31F2NO4/c1-2-30-22(29)12-8-3-4-9-17-26-19(14-16-21(26)28)13-15-20(27)23(24,25)18-10-6-5-7-11-18/h5-7,10-11,13,15,19-20,27H,2-4,8-9,12,14,16-17H2,1H3/b15-13+/t19-,20+/m0/s1

Standard InChI Key:  SGRNLJLJXBPJCJ-VIDFKJSCSA-N

Molfile:  

     RDKit          2D

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   -0.6502   -7.4558    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792   -7.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1647   -6.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6558   -7.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1702   -7.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7157   -8.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202   -8.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8753   -6.2716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3473   -9.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7358   -6.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0213   -5.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -6.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4077   -5.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221   -6.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4077   -4.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -5.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5511   -6.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 15  1  0
  7  8  1  0
 15 16  2  0
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  4  6  1  0
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  6 10  2  0
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  3  2  1  0
  5 21  1  0
  9 11  1  1
 21 22  1  0
 22 23  1  0
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  2  1  1  0
 24 25  1  0
 12 13  1  0
 25 26  1  0
 13  2  1  0
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  4  5  1  0
 26 28  2  0
 13 14  1  6
 27 29  1  0
  6  7  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956374

   ethyl 7-[(2R)-2-[(E,3R)-4,4-difluoro-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl]heptanoate

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: 423.50

Molecular Weight (Monoisotopic): 423.2221

AlogP: 4.20

#Rotatable Bonds: 12

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.10

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -0.04

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