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

ID: ALA3805176

PubChem CID: 127052614

Max Phase: Preclinical

Molecular Formula: C22H25NO5S

Molecular Weight: 415.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc([C@H]2CC[C@@H]3[C@@H](/C=C/CCOc4ccccc4)[C@H](O)C[C@@H]3O2)n1

Standard InChI:  InChI=1S/C22H25NO5S/c24-18-12-20-16(9-10-19(28-20)21-23-17(13-29-21)22(25)26)15(18)8-4-5-11-27-14-6-2-1-3-7-14/h1-4,6-8,13,15-16,18-20,24H,5,9-12H2,(H,25,26)/b8-4+/t15-,16-,18-,19-,20+/m1/s1

Standard InChI Key:  GJEDKMXFVUIJBT-QEJOXDNVSA-N

Molfile:  

     RDKit          2D

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   -3.6168   -1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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    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
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    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
    3.7889    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
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 15 18  1  1
 16 29  1  6
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 10 30  1  1
  9 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3805176

   ---

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: 415.51

Molecular Weight (Monoisotopic): 415.1453

AlogP: 4.08

#Rotatable Bonds: 7

Polar Surface Area: 88.88

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: -0.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 0.88

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