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

ID: ALA1830040

PubChem CID: 56673835

Max Phase: Preclinical

Molecular Formula: C24H30O5

Molecular Weight: 398.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc([C@H]2CC[C@]3(CC2)COC2(OO3)C3CC4CC(C3)CC2C4)cc1

Standard InChI:  InChI=1S/C24H30O5/c25-22(26)19-3-1-17(2-4-19)18-5-7-23(8-6-18)14-27-24(29-28-23)20-10-15-9-16(12-20)13-21(24)11-15/h1-4,15-16,18,20-21H,5-14H2,(H,25,26)/t15?,16?,18-,20?,21?,23-,24?

Standard InChI Key:  JRWHTNNPJJPNLN-LBMIRWHSSA-N

Molfile:  

     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   13.1223  -13.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0225  -12.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9331  -13.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5090  -13.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4353  -13.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2508  -13.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3599  -12.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1737  -12.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4211  -12.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6682  -12.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3274  -12.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9097  -12.2228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0832  -12.2253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0858  -13.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9187  -13.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7368  -13.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5555  -13.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9712  -12.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5617  -12.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7368  -12.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7983  -12.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2037  -13.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0300  -13.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4477  -12.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0330  -12.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2080  -12.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2748  -12.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6860  -13.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6907  -12.2484    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  1
 10  8  1  0
 21 22  2  0
  8  9  1  0
 22 23  1  0
 11 12  1  6
 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:

   

   ALA1830040

   CID 56673835

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: 398.50

Molecular Weight (Monoisotopic): 398.2093

AlogP: 4.91

#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: 5.34

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: 0.75

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