Sodium 1-(2-(4-Dispiro[adamantane-2,3'-[1,2,4]trioxolane-5',1''-cyclohexan]-4''-yl)phenoxy)ethyl)piperidine-4-carboxylate

ID: ALA4514211

PubChem CID: 155539398

Max Phase: Preclinical

Molecular Formula: C30H40NNaO6

Molecular Weight: 511.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C([O-])C1CCN(CCOc2ccc([C@H]3CC[C@]4(CC3)OOC3(O4)C4CC5CC(C4)CC3C5)cc2)CC1.[Na+]

Standard InChI:  InChI=1S/C30H41NO6.Na/c32-28(33)24-7-11-31(12-8-24)13-14-34-27-3-1-22(2-4-27)23-5-9-29(10-6-23)35-30(37-36-29)25-16-20-15-21(18-25)19-26(30)17-20;/h1-4,20-21,23-26H,5-19H2,(H,32,33);/q;+1/p-1/t20?,21?,23-,25?,26?,29+,30?;

Standard InChI Key:  MRWKIDCOOXSHGY-OZAQGSSQSA-M

Molfile:  

     RDKit          2D

 38 43  0  0  0  0  0  0  0  0999 V2000
   21.1832   -6.8647    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   18.0493   -2.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2611   -3.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0538   -3.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6402   -2.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4243   -1.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6260   -1.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6073   -3.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2464   -3.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4133   -3.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9555   -3.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1635   -3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7091   -3.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4064   -2.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9653   -1.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2419   -2.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7150   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3972   -2.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7700   -1.4576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9413   -1.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4381   -2.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6454   -3.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4426   -3.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0304   -3.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8116   -2.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0149   -2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8246   -3.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0367   -4.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8307   -4.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0429   -5.3295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4591   -5.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6684   -6.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4617   -6.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0458   -6.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8366   -5.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6708   -7.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0866   -8.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4641   -7.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  8 10  1  0
  9 11  1  0
 10 12  1  0
 11 13  1  0
 12 13  1  0
 14 15  1  0
 10 14  1  0
  9 16  1  0
 13 17  1  0
 17 15  1  0
 15 16  1  0
 18  2  1  0
  2 19  1  1
 19 20  1  0
 17 20  1  0
 17 18  1  0
  5 21  1  1
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  2  0
 36 38  1  0
M  CHG  2   1   1  38  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 511.66

Molecular Weight (Monoisotopic): 511.2934

AlogP: 5.35

#Rotatable Bonds: 6

Polar Surface Area: 77.46

Molecular Species: ZWITTERION

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.69

CX Basic pKa: 8.96

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.52

Np Likeness Score: 0.28

References

1. Wu J, Wang X, Chiu FCK, Häberli C, Shackleford DM, Ryan E, Kamaraj S, Bulbule VJ, Wallick AI, Dong Y, White KL, Davis PH, Charman SA, Keiser J, Vennerstrom JL..  (2020)  Structure-Activity Relationship of Antischistosomal Ozonide Carboxylic Acids.,  63  (7): [PMID:32134263] [10.1021/acs.jmedchem.0c00069]

Source

Source(1):

• Scientific Literature