3-[(3S,5aR,6R,7R,8aS)-7-Hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-3-yl]propanoic acid

ID: ALA3984438

PubChem CID: 134157766

Max Phase: Preclinical

Molecular Formula: C22H30O6

Molecular Weight: 390.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](O)COc3ccccc3)[C@H](O)C[C@@H]2OC1

Standard InChI:  InChI=1S/C22H30O6/c23-16(14-27-17-4-2-1-3-5-17)8-10-18-19-9-6-15(7-11-22(25)26)13-28-21(19)12-20(18)24/h1-5,8,10,15-16,18-21,23-24H,6-7,9,11-14H2,(H,25,26)/b10-8+/t15-,16+,18+,19+,20+,21-/m0/s1

Standard InChI Key:  IYVIISGTDLLJJD-UWXHIMLYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.8403  -15.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564  -16.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226  -16.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043  -16.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334  -16.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2192  -16.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9483  -16.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1717  -17.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401  -17.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6341  -16.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6252  -17.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144  -17.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9091  -18.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125  -19.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234  -18.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276  -17.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7481  -14.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567  -13.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227  -13.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855  -15.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2895  -15.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488  -14.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3246  -13.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3209  -12.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060  -12.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042  -11.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0861  -11.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141  -10.9861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905  -15.6319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980  -14.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 21  1  1  0
  1  2  1  0
  2  3  1  0
  3 20  1  0
  3  4  1  1
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  2  9  1  6
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 18 19  1  0
 20 17  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 20 21  1  0
 19 24  1  6
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 20 29  1  1
 21 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3984438

   ---

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: 2.64

#Rotatable Bonds: 8

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: 4.44

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: -0.81

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: 1.01

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