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

ID: ALA3805455

PubChem CID: 126495420

Max Phase: Preclinical

Molecular Formula: C23H29NO5S

Molecular Weight: 431.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc([C@H]2CC[C@@H]3[C@@H](CCCCCOc4ccccc4)[C@H](O)C[C@@H]3O2)n1

Standard InChI:  InChI=1S/C23H29NO5S/c25-19-13-21-17(10-11-20(29-21)22-24-18(14-30-22)23(26)27)16(19)9-5-2-6-12-28-15-7-3-1-4-8-15/h1,3-4,7-8,14,16-17,19-21,25H,2,5-6,9-13H2,(H,26,27)/t16-,17-,19-,20-,21+/m1/s1

Standard InChI Key:  ITJGRSUVRVMJDN-FLTCSQOGSA-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
   -4.9669   -0.8711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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    5.5870    4.6698    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
    6.0553    6.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5241    6.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    7.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4598    8.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9249    9.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224   10.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4549   10.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9898    8.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  4  6  1  0
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  9 14  1  0
 15 16  1  0
 16 17  1  0
  9 17  1  0
 10 15  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 15 18  1  1
 16 22  1  6
 13  2  1  1
 10 23  1  1
  9 24  1  1
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805455

   ---

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: 431.55

Molecular Weight (Monoisotopic): 431.1766

AlogP: 4.70

#Rotatable Bonds: 9

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: 4.11

CX LogD: 0.66

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: 0.65

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