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

ID: ALA1830033

PubChem CID: 56677169

Max Phase: Preclinical

Molecular Formula: C18H26O5

Molecular Weight: 322.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H26O5/c19-16(20)13-1-3-17(4-2-13)10-21-18(23-22-17)14-6-11-5-12(8-14)9-15(18)7-11/h11-15H,1-10H2,(H,19,20)/t11?,12?,13-,14?,15?,17-,18?

Standard InChI Key:  ZHMJENXLKLCUDS-MDSGESRMSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   12.5426   -3.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4446   -3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3550   -3.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9322   -3.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8583   -4.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6754   -4.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7827   -2.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5982   -2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8440   -2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0937   -3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7564   -3.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3378   -2.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5096   -2.5769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5123   -4.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3467   -4.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1666   -4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9871   -4.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4035   -3.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9933   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1666   -2.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2323   -3.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6434   -4.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6501   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  6
  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
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830033

   CID 56677169

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: 322.40

Molecular Weight (Monoisotopic): 322.1780

AlogP: 3.13

#Rotatable Bonds: 1

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: 3.85

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 0.25

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: 0.99

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