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

ID: ALA1096762

PubChem CID: 46238242

Max Phase: Preclinical

Molecular Formula: C18H25FO5

Molecular Weight: 340.39

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)C3F

Standard InChI:  InChI=1S/C18H25FO5/c19-16-11-6-13-8-12(16)9-14(7-11)18(13)22-17(23-24-18)3-1-10(2-4-17)5-15(20)21/h10-14,16H,1-9H2,(H,20,21)/t10-,11?,12?,13?,14?,16?,17+,18-

Standard InChI Key:  FARUTZQUEHNLJH-CPJYYCRESA-N

Molfile:  

     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
   -0.2041  -21.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040  -21.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1457  -20.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914  -22.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204  -20.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202  -21.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578  -20.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281  -21.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531  -21.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824  -20.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450  -21.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283  -20.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950  -22.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692  -21.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7401  -21.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3320  -20.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819  -22.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074  -20.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574  -22.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932  -21.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311  -22.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477  -22.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578  -22.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3273  -22.1540    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
  6  2  1  0
 15 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096762

   CID 46238242

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: 340.39

Molecular Weight (Monoisotopic): 340.1686

AlogP: 3.43

#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: 3.45

CX LogD: 0.24

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.78

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