3,4-bis(benzyloxy)furan-2,5-dicarboxylic acid

ID: ALA2261214

PubChem CID: 2801517

Max Phase: Preclinical

Molecular Formula: C20H16O7

Molecular Weight: 368.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1oc(C(=O)O)c(OCc2ccccc2)c1OCc1ccccc1

Standard InChI:  InChI=1S/C20H16O7/c21-19(22)17-15(25-11-13-7-3-1-4-8-13)16(18(27-17)20(23)24)26-12-14-9-5-2-6-10-14/h1-10H,11-12H2,(H,21,22)(H,23,24)

Standard InChI Key:  ZHFHXTPKRGXQSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   14.1162  -11.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7769  -12.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4508  -11.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2019  -10.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3782  -10.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6344  -10.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9035  -10.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4595  -10.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8919   -9.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7152   -9.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1435   -8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7507   -7.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9214   -7.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4927   -8.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0783  -10.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6725   -9.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -8.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6909   -7.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8647   -7.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4453   -8.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8486   -9.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2772  -11.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6691  -12.2924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7062  -10.8663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3877  -11.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6834  -11.4923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3660  -12.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  4  6  1  0
  5  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 22 24  2  0
  3 22  1  0
 25 26  1  0
 25 27  2  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2261214

   3,4-Di(benzyloxy) furan-2,5-dicarboxylic acid

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: 368.34

Molecular Weight (Monoisotopic): 368.0896

AlogP: 3.83

#Rotatable Bonds: 8

Polar Surface Area: 106.20

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.47

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: -3.07

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.10

References

1. Magesh S, Moriya S, Suzuki T, Miyagi T, Ishida H, Kiso M.  (2010)  Use of structure-based virtual screening in the investigation of novel human sialidase inhibitors,  19  (9): [10.1007/s00044-009-9269-6]

Source

Source(1):

• Scientific Literature