trans-Adamantane-2-spiro-3'-9'-carboxymethyl-1',2',4'-trioxaspiro[5.5]undecane

ID: ALA1830029

PubChem CID: 56673833

Max Phase: Preclinical

Molecular Formula: C19H28O5

Molecular Weight: 336.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H]1CC[C@]2(CC1)COC1(OO2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C19H28O5/c20-17(21)10-12-1-3-18(4-2-12)11-22-19(24-23-18)15-6-13-5-14(8-15)9-16(19)7-13/h12-16H,1-11H2,(H,20,21)/t12-,13?,14?,15?,16?,18-,19?

Standard InChI Key:  UQJCLZIJKYZSQC-WBDWUYMBSA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    8.3387    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2407    1.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511    0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7283    0.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6544   -0.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4714    0.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5789    1.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3942    1.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6402    1.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8896    0.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5521    0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1336    1.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3054    1.6591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3080    0.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1425    0.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9623    0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7826    0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1991    0.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7888    1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9623    1.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0278    0.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4388    0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2675    0.2076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0211   -0.5044    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  1
 10  8  1  0
 21 22  1  0
  8  9  1  0
 22 23  2  0
 11 12  1  6
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830029

   CID 56673833

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: 3.67

CX LogD: 0.52

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 1.02

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