cis-6,6-Difluoroadamantane-2-spiro-3'-8'-carboxymethyl-1',2',4'-trioxaspiro[4.5]decane

ID: ALA1096763

PubChem CID: 46238243

Max Phase: Preclinical

Molecular Formula: C18H24F2O5

Molecular Weight: 358.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H]1CC[C@]2(CC1)OO[C@]1(O2)C2CC3CC1CC(C2)C3(F)F

Standard InChI:  InChI=1S/C18H24F2O5/c19-17(20)11-6-13-8-12(17)9-14(7-11)18(13)23-16(24-25-18)3-1-10(2-4-16)5-15(21)22/h10-14H,1-9H2,(H,21,22)/t10-,11?,12?,13?,14?,16+,18-

Standard InChI Key:  RXAVXHMQGMZABO-FWABDUALSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    0.9827  -25.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908  -25.7935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325  -24.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955  -25.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664  -24.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070  -25.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446  -24.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7413  -25.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6663  -25.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956  -24.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582  -25.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3415  -24.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082  -26.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9560  -25.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533  -25.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188  -24.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688  -26.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943  -24.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442  -26.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801  -25.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2179  -25.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345  -26.7222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446  -25.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695  -25.0981    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405  -26.0933    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0
  8 12  1  0
  9 10  1  0
 10  5  1  0
 11  4  1  0
 12  5  1  0
 13  4  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
  9 11  1  0
  6  7  1  1
  9 15  1  0
 16 14  1  0
 14 20  1  1
  2  1  1  0
 20 21  1  0
  1  3  1  1
  4  1  1  0
 21 22  1  0
 21 23  2  0
  5  1  1  0
 15 24  1  0
  6  2  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096763

   CID 46238243

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: 358.38

Molecular Weight (Monoisotopic): 358.1592

AlogP: 3.72

#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: 3.90

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 0.45

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: 1.29

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