2-{(2R,4aR,5R,6R,7aS)-6-hydroxy-5-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]octahydrocyclopenta[b]pyran-2-yl}-1,3-thiazole-4-carboxylic acid

ID: ALA3804978

PubChem CID: 127052613

Max Phase: Preclinical

Molecular Formula: C22H25NO6S

Molecular Weight: 431.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](O)COc4ccccc4)[C@H](O)C[C@@H]3O2)n1

Standard InChI:  InChI=1S/C22H25NO6S/c24-13(11-28-14-4-2-1-3-5-14)6-7-15-16-8-9-19(29-20(16)10-18(15)25)21-23-17(12-30-21)22(26)27/h1-7,12-13,15-16,18-20,24-25H,8-11H2,(H,26,27)/b7-6+/t13-,15-,16-,18-,19-,20+/m1/s1

Standard InChI Key:  NATVOQPMZYYFRA-BNLVXIRVSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.7580   -2.9756    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168   -1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.8711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730   -1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4631   -1.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1691   -2.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9507   -0.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    6.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241    6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9941    7.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4627    8.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4614    7.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9914    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5228    5.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178    5.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035    1.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -1.7412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  2  0
  6  8  1  0
  4  6  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 14  1  0
 15 16  1  0
 16 17  1  0
  9 17  1  0
 10 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 22 23  1  0
 21 22  1  0
 20 29  1  1
 15 18  1  1
 16 30  1  6
 13  2  1  1
 10 31  1  1
  9 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3804978

   ---

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: 431.51

Molecular Weight (Monoisotopic): 431.1403

AlogP: 3.05

#Rotatable Bonds: 7

Polar Surface Area: 109.11

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 2.38

CX LogD: -1.07

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: 0.71

References

1. Ogawa S, Watanabe T, Sugimoto I, Moriyuki K, Goto Y, Yamane S, Watanabe A, Tsuboi K, Kinoshita A, Kigoshi H, Tani K, Maruyama T..  (2016)  Discovery of G Protein-Biased EP2 Receptor Agonists.,  7  (3): [PMID:26985320] [10.1021/acsmedchemlett.5b00455]

Source

Source(1):

• Scientific Literature