Adamantane-2-spiro-3'-9'-carboxymethyl-1',2',5'-trioxaspiro[5.5]undecane

ID: ALA1830031

PubChem CID: 56680480

Max Phase: Preclinical

Molecular Formula: C19H28O5

Molecular Weight: 336.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC1CCC2(CC1)OCC1(OO2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C19H28O5/c20-17(21)10-12-1-3-18(4-2-12)22-11-19(24-23-18)15-6-13-5-14(8-15)9-16(19)7-13/h12-16H,1-11H2,(H,20,21)

Standard InChI Key:  XUNUTOXIXGSNCX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   -5.0086   -3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -3.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1962   -3.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6192   -3.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -4.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684   -2.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073   -2.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -3.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -3.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2137   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -2.3882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -3.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048   -3.8279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851   -3.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -3.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8517   -3.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415   -2.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6804   -3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915   -3.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202   -3.8397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738   -4.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  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  1  0
  8  9  1  0
 22 23  2  0
 11 12  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830031

   CID 56680480

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: 336.43

Molecular Weight (Monoisotopic): 336.1937

AlogP: 3.52

#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: 4.00

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 0.29

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 1.23

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