US9156810, 43

ID: ALA3966610

PubChem CID: 10045223

Max Phase: Preclinical

Molecular Formula: C22H34O5

Molecular Weight: 378.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H34O5/c1-4-5-8-11-16(23)14-15-18-17(20(26)22(2,3)21(18)27)12-9-6-7-10-13-19(24)25/h14-18,21,23,27H,4-5,7-8,10-13H2,1-3H3,(H,24,25)/b15-14+/t16-,17+,18+,21-/m0/s1

Standard InChI Key:  YQYNOBUZBOFQFN-SFKLEDFFSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  1  0  0  0  0  0999 V2000
    1.9402  -11.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298  -10.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -8.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -7.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830   -6.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954   -4.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890   -4.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -3.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6281   -2.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0481    1.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480    1.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3548    0.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179   -1.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1103   -1.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9950   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4873   -2.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3720   -4.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5653   -3.9040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8859   -5.1283    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
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
 10  9  1  6
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 10  1  0
 18 19  1  1
 19 20  1  0
 20 21  3  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3966610

   7-[(1R,4S,5R)-4-hydroxy-5-[(E,3S)-3-hydroxyoct-1-enyl]-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: 378.51

Molecular Weight (Monoisotopic): 378.2406

AlogP: 3.33

#Rotatable Bonds: 10

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: 4.07

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 1.15

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: 1.67

References

1.  (2015)  Treatment of inflammatory bowel disease, 

Source

Source(1):

• BindingDB Database