Adamantane-2-spiro-3'-9'-carboxy-1',2',4',5'-tetraoxaspiro[5.5]undecane

ID: ALA1830034

PubChem CID: 56660000

Max Phase: Preclinical

Molecular Formula: C17H24O6

Molecular Weight: 324.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1CCC2(CC1)OOC1(OO2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C17H24O6/c18-15(19)12-1-3-16(4-2-12)20-22-17(23-21-16)13-6-10-5-11(8-13)9-14(17)7-10/h10-14H,1-9H2,(H,18,19)

Standard InChI Key:  QLBXWPYRCIWKCQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
   -4.6824   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7804   -6.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8700   -7.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929   -7.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -7.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496   -7.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4423   -6.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6268   -6.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810   -6.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1314   -6.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -6.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -6.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155   -6.1220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7129   -7.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8784   -7.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -7.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -7.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -6.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7680   -6.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -6.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070   -6.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181   -7.5698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246   -6.1343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
 11 15  1  0
 12 13  1  0
 13 10  1  0
 10 14  1  0
 14 15  1  0
 11 16  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
 11 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  6 10  1  0
 18 21  1  0
 10  8  1  0
 21 22  1  0
  8  9  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1830034

   CID 56660000

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: 324.37

Molecular Weight (Monoisotopic): 324.1573

AlogP: 3.02

#Rotatable Bonds: 1

Polar Surface Area: 74.22

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.68

CX Basic pKa: ┄

CX LogP: 3.79

CX LogD: 0.47

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: 0.93

References

1. Wang X, Zhao Q, Vargas M, Dong Y, Sriraghavan K, Keiser J, Vennerstrom JL..  (2011)  The activity of dispiro peroxides against Fasciola hepatica.,  21  (18): [PMID:21802291] [10.1016/j.bmcl.2011.07.024]

2. Yang J, Tu Z, Xu X, Luo J, Yan X, Ran C, Mao X, Ding K, Qiao C..  (2017)  Novel conjugates of endoperoxide and 4-anilinoquinazoline as potential anticancer agents.,  27  (6): [PMID:28236592] [10.1016/j.bmcl.2017.02.023]

Source

Source(1):

• Scientific Literature