trans-Adamantane-2-spiro-3'-7'-carboxymethyl-1',2',4'-trioxaspiro[4.5]decane

ID: ALA3084740

PubChem CID: 46238108

Max Phase: Preclinical

Molecular Formula: C18H26O5

Molecular Weight: 322.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@@H]1CCC[C@]2(C1)OOC1(O2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C18H26O5/c19-16(20)9-11-2-1-3-17(10-11)21-18(23-22-17)14-5-12-4-13(7-14)8-15(18)6-12/h11-15H,1-10H2,(H,19,20)/t11-,12?,13?,14?,15?,17+,18?/m0/s1

Standard InChI Key:  MMZNSLVQJVAATJ-KERRXJBBSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   16.6586  -11.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4225  -11.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1262  -11.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9230  -10.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1081  -10.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3622  -12.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5610  -12.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3725   -9.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6370  -10.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3725  -10.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1876  -11.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1081   -9.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9230  -10.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6226  -13.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6370   -9.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7686  -12.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8464  -13.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1384  -12.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2162  -13.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5448  -12.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1750  -13.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9512  -12.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0290  -13.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8 12  1  0
  9 10  1  0
 10  5  1  0
 11  4  1  0
  4  1  1  0
  9 11  1  0
 14 17  1  0
 15  8  1  0
 16 18  1  0
 17 19  1  0
 18  6  1  0
 19  6  1  0
  8 13  1  0
 13  4  1  0
  6  7  1  1
  9 15  1  0
 16 14  1  0
 16 20  1  6
  2  1  1  0
 20 21  1  0
  1  3  1  0
 12  5  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3084740

   2-((1R,3R,3''R,5R,5'R,7R)-Dispiro[adamantane-2,3'-[1,2,4]trioxolane-5',1''-cyclohexan]-3''-YL)acetic acid

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: 3.48

#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: 4.26

CX Basic pKa: ┄

CX LogP: 3.79

CX LogD: 0.80

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: 1.40

References

1. Zhao Q, Vargas M, Dong Y, Zhou L, Wang X, Sriraghavan K, Keiser J, Vennerstrom JL..  (2010)  Structure-activity relationship of an ozonide carboxylic acid (OZ78) against Fasciola hepatica.,  53  (10): [PMID:20423101] [10.1021/jm100226t]

Source

Source(1):

• Scientific Literature