4-{dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1''-cyclohexane]-4''-yl}benzoic acid

ID: ALA1830039

PubChem CID: 20801772

Max Phase: Preclinical

Molecular Formula: C23H28O5

Molecular Weight: 384.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(C2CCC3(CC2)OOC2(O3)C3CC4CC(C3)CC2C4)cc1

Standard InChI:  InChI=1S/C23H28O5/c24-21(25)18-3-1-16(2-4-18)17-5-7-22(8-6-17)26-23(28-27-22)19-10-14-9-15(12-19)13-20(23)11-14/h1-4,14-15,17,19-20H,5-13H2,(H,24,25)

Standard InChI Key:  GOIAJBVFHMOJSY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 33  0  0  0  0  0  0  0  0999 V2000
    2.7656  -13.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672  -13.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5777  -13.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546  -13.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807  -14.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975  -13.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0051  -12.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202  -12.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0665  -12.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3155  -13.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483  -13.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0584  -13.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8784  -13.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2947  -13.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8846  -12.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0584  -12.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894  -13.7321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3798  -12.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532  -12.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1189  -13.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292  -13.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3568  -13.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7751  -13.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3598  -12.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5335  -12.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6035  -13.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0154  -13.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0201  -12.5398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  4  6  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
 17 11  1  0
 11 18  1  0
 18 19  1  0
 19 10  1  0
  2  9  1  0
  6 10  1  0
 20 21  2  0
 10  8  1  0
 21 22  1  0
  8  9  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 14 20  1  0
  1  2  1  0
 23 26  1  0
  1  3  1  0
 26 27  1  0
  2  4  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830039

   CID 20801772

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: 384.47

Molecular Weight (Monoisotopic): 384.1937

AlogP: 4.87

#Rotatable Bonds: 2

Polar Surface Area: 64.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.22

CX Basic pKa: ┄

CX LogP: 5.46

CX LogD: 2.44

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: 1.01

References

1. Wang X, Zhao Q, Vargas M, Dong Y, Sriraghavan K, Keiser J, Vennerstrom JL..  (2011)  The activity of dispiro peroxides against Fasciola hepatica.,  21  (18): [PMID:21802291] [10.1016/j.bmcl.2011.07.024]

Source

Source(1):

• Scientific Literature