Adamantane-2-spiro-3'-9'-(4'-carboxyphenyl)-1',2',4',5'-tetraoxaspiro[5.5]undecane

ID: ALA1830041

PubChem CID: 56677170

Max Phase: Preclinical

Molecular Formula: C23H28O6

Molecular Weight: 400.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(C2CCC3(CC2)OOC2(OO3)C3CC4CC(C3)CC2C4)cc1

Standard InChI:  InChI=1S/C23H28O6/c24-21(25)18-3-1-16(2-4-18)17-5-7-22(8-6-17)26-28-23(29-27-22)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:  UEJJZZBURNQCCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   -4.9778  -17.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0778  -17.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672  -18.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911  -18.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649  -18.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494  -18.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7403  -17.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265  -17.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791  -16.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321  -17.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728  -17.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905  -16.9681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170  -16.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143  -18.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816  -18.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3634  -18.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554  -18.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8709  -17.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616  -16.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3634  -16.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980  -17.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034  -18.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9297  -18.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474  -17.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9327  -16.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1078  -16.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1745  -17.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857  -18.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905  -16.9936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 15  1  0
 12 13  1  0
 13 10  1  0
 10 14  1  0
 14 15  1  0
 11 16  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
 11 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  6 10  1  0
 18 21  1  0
 10  8  1  0
 21 22  2  0
  8  9  1  0
 22 23  1  0
 11 12  1  0
 23 24  2  0
 24 25  1  0
  1  2  1  0
 25 26  2  0
 26 21  1  0
  1  3  1  0
 24 27  1  0
  2  4  1  0
 27 28  1  0
  3  5  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830041

   CID 56677170

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: 400.47

Molecular Weight (Monoisotopic): 400.1886

AlogP: 4.80

#Rotatable Bonds: 2

Polar Surface Area: 74.22

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.22

CX Basic pKa: ┄

CX LogP: 5.64

CX LogD: 2.62

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: 0.70

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