7-((1R,2S,3R)-3-hydroxy-2-(4-(1-hydroxycyclobutyl)phenyl)-5-oxocyclopentyl)hept-5-enoic acid

ID: ALA3985882

PubChem CID: 58681359

Max Phase: Preclinical

Molecular Formula: C22H28O5

Molecular Weight: 372.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc(C2(O)CCC2)cc1

Standard InChI:  InChI=1S/C22H28O5/c23-18-14-19(24)21(17(18)6-3-1-2-4-7-20(25)26)15-8-10-16(11-9-15)22(27)12-5-13-22/h1,3,8-11,17,19,21,24,27H,2,4-7,12-14H2,(H,25,26)/b3-1-/t17-,19+,21+/m0/s1

Standard InChI Key:  IYUJRRJWUAAMRV-VPDRBAPTSA-N

Molfile:  

     RDKit          2D

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    4.0182  -20.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227  -21.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1326  -21.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934  -17.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106  -17.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0650  -17.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020  -16.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433  -17.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008  -15.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122  -18.5727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902  -18.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538  -19.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327  -19.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981  -18.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8425  -16.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4491  -17.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266  -17.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3976  -16.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1752  -16.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462  -15.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1237  -15.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7302  -15.6268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947  -14.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5790  -19.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484  -19.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5418  -20.4719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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  5  6  1  0
  6  7  1  0
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  8  9  1  0
  9  5  1  0
  8 10  2  0
  5 11  1  6
  6 12  1  1
 12 13  2  0
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 14 26  2  0
 25 15  2  0
 15 12  1  0
  7 16  1  6
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
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 22 23  2  0
 22 24  1  0
 25 26  1  0
 26  1  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985882

   (Z)-7-[(1R,2S,3R)-3-hydroxy-2-[4-(1-hydroxycyclobutyl)phenyl]-5-oxocyclopentyl]hept-5-enoic 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: 372.46

Molecular Weight (Monoisotopic): 372.1937

AlogP: 3.29

#Rotatable Bonds: 8

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.29

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: -0.07

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 1.56

References

1.  (2010)  Therapeutic compounds, 

Source

Source(1):

• Patent Bioactivity Data