4-((2R,4aR,5R,6R,7aS)-6-hydroxy-5-((R,E)-3-hydroxy-4-phenoxybut-1-enyl)octahydrocyclopenta[b]pyran-2-yl)butanoic acid

ID: ALA3982726

Cas Number: 72657-07-9

PubChem CID: 6443852

Max Phase: Preclinical

Molecular Formula: C22H30O6

Molecular Weight: 390.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCC[C@@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](O)COc3ccccc3)[C@H](O)C[C@@H]2O1

Standard InChI:  InChI=1S/C22H30O6/c23-15(14-27-16-5-2-1-3-6-16)9-11-18-19-12-10-17(7-4-8-22(25)26)28-21(19)13-20(18)24/h1-3,5-6,9,11,15,17-21,23-24H,4,7-8,10,12-14H2,(H,25,26)/b11-9+/t15-,17-,18-,19-,20-,21+/m1/s1

Standard InChI Key:  FTBNLUSUCXCIGD-OVCPVMRKSA-N

Molfile:  

     RDKit          2D

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   15.2881  -13.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6865  -14.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8643  -15.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6459  -15.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2469  -14.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0654  -14.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2444  -13.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8962  -13.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5763  -13.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490  -13.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9761  -13.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7457  -13.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3768  -12.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8883  -14.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1455  -13.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8637  -14.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5303  -12.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3491  -12.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7863  -11.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4078  -11.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5891  -11.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1488  -11.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2087  -10.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6501   -9.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4719   -9.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9094   -9.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7284   -9.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5342   -8.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1683  -12.5891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7121  -12.4998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
 17  7  1  0
  7  8  1  0
  8  9  1  0
  9 18  1  0
  9 10  1  1
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 13 15  1  0
 15  1  1  0
  8 16  1  6
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  6
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 18 29  1  1
 17 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3982726

   4-[(2R,4aR,5R,6R,7aS)-6-hydroxy-5-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-2,3,4,4a,5,6,7,7a-octahydrocyclopenta[b]pyran-2-yl]butanoic 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: 390.48

Molecular Weight (Monoisotopic): 390.2042

AlogP: 2.78

#Rotatable Bonds: 9

Polar Surface Area: 96.22

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.40

CX Basic pKa: ┄

CX LogP: 2.18

CX LogD: -0.71

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: 1.33

References

1. Sugimoto I, Kambe T, Okino T, Obitsu T, Ohta N, Nishiyama T, Kinoshita A, Fujimoto T, Egashira H, Yamane S, Shuto S, Tani K, Maruyama T..  (2017)  Discovery of Novel Seven-Membered Prostacyclin Analogues as Potent and Selective Prostaglandin FP and EP3 Dual Agonists.,  8  (1): [PMID:28105284] [10.1021/acsmedchemlett.6b00415]

Source

Source(1):

• Scientific Literature