7-((1R,2S,3R,5R)-5-chloro-3-hydroxy-2-(4-(1-hydroxy-2-methylpropan-2-yl)phenyl)cyclopentyl)hept-5-enoic acid

ID: ALA3973312

PubChem CID: 11955235

Max Phase: Preclinical

Molecular Formula: C22H31ClO4

Molecular Weight: 394.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(CO)c1ccc([C@@H]2[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]2O)cc1

Standard InChI:  InChI=1S/C22H31ClO4/c1-22(2,14-24)16-11-9-15(10-12-16)21-17(18(23)13-19(21)25)7-5-3-4-6-8-20(26)27/h3,5,9-12,17-19,21,24-25H,4,6-8,13-14H2,1-2H3,(H,26,27)/b5-3-/t17-,18+,19+,21+/m0/s1

Standard InChI Key:  QKCBLYQALCVPFG-QUUVRLJHSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   30.5496  -14.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5539  -13.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8373  -13.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7955  -10.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6205  -10.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8773  -10.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2080   -9.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5430  -10.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2068   -8.7458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.3097  -11.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1047  -11.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7651  -12.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2484  -12.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9203  -11.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6622   -9.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2745  -10.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0596  -10.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2322   -9.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0171   -9.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1898   -8.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9748   -7.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5871   -8.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1474   -7.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4058  -12.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0720  -12.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3770  -13.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8606  -14.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  7  9  1  1
  4 10  1  6
  5 11  1  1
 11 12  2  0
 12 13  1  0
 13 25  2  0
 24 14  2  0
 14 11  1  0
  6 15  1  6
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 24 25  1  0
 25  2  1  0
  2 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3973312

   (Z)-7-[(1R,2S,3R,5R)-5-chloro-3-hydroxy-2-[4-(1-hydroxy-2-methylpropan-2-yl)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: 394.94

Molecular Weight (Monoisotopic): 394.1911

AlogP: 4.23

#Rotatable Bonds: 9

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.44

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 0.99

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: 1.11

References

1.  (2010)  Therapeutic compounds, 

Source

Source(1):

• Patent Bioactivity Data