7-((1R,2S,3R,5R)-5-chloro-3-hydroxy-2-(3-(hydroxy(1-propylcyclobutyl)methyl)phenyl)cyclopentyl)hept-5-enoic acid

ID: ALA3982222

PubChem CID: 11955178

Max Phase: Preclinical

Molecular Formula: C26H37ClO4

Molecular Weight: 449.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC1(C(O)c2cccc([C@@H]3[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]3O)c2)CCC1

Standard InChI:  InChI=1S/C26H37ClO4/c1-2-13-26(14-8-15-26)25(31)19-10-7-9-18(16-19)24-20(21(27)17-22(24)28)11-5-3-4-6-12-23(29)30/h3,5,7,9-10,16,20-22,24-25,28,31H,2,4,6,8,11-15,17H2,1H3,(H,29,30)/b5-3-/t20-,21+,22+,24+,25?/m0/s1

Standard InChI Key:  NJOXKYGJCYOIRG-PBNZNZKVSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   25.4097  -22.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6998  -22.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1042  -23.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8141  -23.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5317  -20.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3489  -20.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6033  -19.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9403  -19.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2816  -19.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9391  -18.5973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0505  -21.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8285  -21.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4921  -22.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9710  -22.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7847  -22.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1173  -21.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6364  -21.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3808  -19.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9874  -20.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7649  -19.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9359  -19.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7135  -18.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8845  -18.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6620  -17.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8330  -17.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2685  -18.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9298  -21.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2604  -21.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2242  -22.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7061  -23.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5186  -22.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  1  1
  5 11  1  6
  6 12  1  1
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  7 18  1  6
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 16 27  1  0
 27  1  1  0
 27 28  1  0
  1 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982222

   (Z)-7-[(1R,2S,3R,5R)-5-chloro-3-hydroxy-2-[3-[hydroxy-(1-propylcyclobutyl)methyl]phenyl]cyclopentyl]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: 449.03

Molecular Weight (Monoisotopic): 448.2380

AlogP: 5.96

#Rotatable Bonds: 11

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.43

CX Basic pKa: ┄

CX LogP: 5.36

CX LogD: 2.50

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: 1.53

References

1.  (2010)  Therapeutic compounds, 

Source

Source(1):

• Patent Bioactivity Data