US9156810, (74, 75)

ID: ALA3954031

PubChem CID: 10434119

Max Phase: Preclinical

Molecular Formula: C26H30O5S

Molecular Weight: 454.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)[C@H](CC#CCCCC(=O)O)[C@@H](/C=C/C(O)Cc2cc3ccccc3s2)[C@@H]1O

Standard InChI:  InChI=1S/C26H30O5S/c1-26(2)24(30)20(10-5-3-4-6-12-23(28)29)21(25(26)31)14-13-18(27)16-19-15-17-9-7-8-11-22(17)32-19/h7-9,11,13-15,18,20-21,25,27,31H,4,6,10,12,16H2,1-2H3,(H,28,29)/b14-13+/t18?,20-,21-,25+/m1/s1

Standard InChI Key:  MNSSULPKPIROKW-ZNVAMYPYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    5.2934  -10.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3332  -11.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4409  -12.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0214   -9.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8190   -8.8637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7928   -8.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -7.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -5.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974   -5.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195  -10.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429  -10.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369   -9.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5308   -7.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019   -8.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9958   -7.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4668   -7.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2616   -6.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8485   -8.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0342  -11.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087  -13.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  1
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
 20 12  1  0
  6 21  1  0
 21 22  1  6
 22 23  1  0
 23 24  3  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 21 31  1  0
 31  2  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3954031

   7-[(1R,4S,5R)-5-[(E)-4-(1-benzothiophen-2-yl)-3-hydroxybut-1-enyl]-4-hydroxy-3,3-dimethyl-2-oxocyclopentyl]hept-5-ynoic 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: 454.59

Molecular Weight (Monoisotopic): 454.1814

AlogP: 4.21

#Rotatable Bonds: 8

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 5.08

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.76

References

1.  (2015)  Treatment of inflammatory bowel disease, 

Source

Source(1):

• BindingDB Database