Adamantane-2-spiro-2'-8'-carboxymethyl-1',4'-dioxaspiro[4.5]-decane

ID: ALA1097076

PubChem CID: 46238245

Max Phase: Preclinical

Molecular Formula: C19H28O4

Molecular Weight: 320.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H]1CC[C@]2(CC1)OC[C@]1(O2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C19H28O4/c20-17(21)10-12-1-3-18(4-2-12)22-11-19(23-18)15-6-13-5-14(8-15)9-16(19)7-13/h12-16H,1-11H2,(H,20,21)/t12-,13?,14?,15?,16?,18-,19-

Standard InChI Key:  DPSRDOLVGHIHDT-CNORFBFWSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   20.1551  -21.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7631  -22.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5049  -21.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7679  -22.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6387  -21.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4794  -21.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3170  -21.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4311  -22.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5061  -21.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8767  -21.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0141  -22.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8309  -21.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9641  -22.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1284  -21.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6191  -22.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6912  -21.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7412  -22.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8667  -21.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9166  -22.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9524  -21.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3902  -22.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0068  -23.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2169  -22.5491    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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA1097076

   CID 46238245

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: 320.43

Molecular Weight (Monoisotopic): 320.1988

AlogP: 3.59

#Rotatable Bonds: 2

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 0.14

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.84

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