2-(4-(4-dispiro[adamantane-2,3'-[1,2,4]trioxolane-5',1''-cyclohexan]-4''-yl)phenoxy)piperidin-1-yl)acetic acid

ID: ALA4483675

PubChem CID: 155540628

Max Phase: Preclinical

Molecular Formula: C29H39NO6

Molecular Weight: 497.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CN1CCC(Oc2ccc([C@H]3CC[C@]4(CC3)OOC3(O4)C4CC5CC(C4)CC3C5)cc2)CC1

Standard InChI:  InChI=1S/C29H39NO6/c31-27(32)18-30-11-7-26(8-12-30)33-25-3-1-21(2-4-25)22-5-9-28(10-6-22)34-29(36-35-28)23-14-19-13-20(16-23)17-24(29)15-19/h1-4,19-20,22-24,26H,5-18H2,(H,31,32)/t19?,20?,22-,23?,24?,28+,29?

Standard InChI Key:  OMXDTNRBKFIPGD-JMXSTCCASA-N

Molfile:  

 
     RDKit          2D

 36 42  0  0  0  0  0  0  0  0999 V2000
   31.1358   -2.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3463   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1340   -3.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7167   -2.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5021   -2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7089   -1.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7152   -3.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3503   -3.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5161   -3.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0550   -3.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2617   -4.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8040   -3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5094   -2.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0648   -2.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3459   -2.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8098   -2.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4876   -3.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8582   -1.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0347   -1.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5097   -3.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7158   -3.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5079   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0921   -3.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8746   -2.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0829   -2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8813   -3.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0920   -4.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5073   -5.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7153   -5.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5037   -6.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0841   -5.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8762   -4.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7115   -6.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1309   -7.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3387   -8.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3426   -7.3285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  7  9  1  0
  8 10  1  0
  9 11  1  0
 10 12  1  0
 11 12  1  0
 13 14  1  0
  9 13  1  0
  8 15  1  0
 12 16  1  0
 16 14  1  0
 14 15  1  0
 17  1  1  0
  1 18  1  1
 18 19  1  0
 16 19  1  0
 16 17  1  0
  4 20  1  1
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483675

   ---

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: 497.63

Molecular Weight (Monoisotopic): 497.2777

AlogP: 5.10

#Rotatable Bonds: 5

Polar Surface Area: 77.46

Molecular Species: ZWITTERION

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.37

CX Basic pKa: 9.17

CX LogP: 2.42

CX LogD: 2.41

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.57

Np Likeness Score: 0.50

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