ID: ALA228397

Max Phase: Preclinical

Molecular Formula: C27H20O6

Molecular Weight: 440.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1cc(Cc2cc(C(=O)O)c(O)c(-c3ccccc3)c2)cc(-c2ccccc2)c1O

Standard InChI:  InChI=1S/C27H20O6/c28-24-20(18-7-3-1-4-8-18)12-16(14-22(24)26(30)31)11-17-13-21(19-9-5-2-6-10-19)25(29)23(15-17)27(32)33/h1-10,12-15,28-29H,11H2,(H,30,31)(H,32,33)

Standard InChI Key:  NPOVMAFHVDLXQA-UHFFFAOYSA-N

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

Properties

Molecular Weight: 440.45

Molecular Weight (Monoisotopic): 440.1260

AlogP: 5.42

#Rotatable Bonds: 6

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.40

CX Basic pKa:

CX LogP: 7.37

CX LogD: 0.37

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: 0.13

References

1. Shrestha S, Bhattarai BR, Lee KH, Cho H..  (2007)  Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs.,  15  (20): [PMID:17692525] [10.1016/j.bmc.2007.07.010]

2. Shrestha S, Bhattarai BR, Chang KJ, Lee KH, Cho H..  (2007)  Methylenedisalicylic acid derivatives: new PTP1B inhibitors that confer resistance to diet-induced obesity.,  17  (10): [PMID:17368023] [10.1016/j.bmcl.2007.02.069]

3. Shrestha S, Bhattarai BR, Kafle B, Lee KH, Cho H..  (2008)  Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity.,  16  (18): [PMID:18722777] [10.1016/j.bmc.2008.07.090]

4. Bhattarai BR, Ko JH, Shrestha S, Kafle B, Cho H, Kang JH, Cho H..  (2010)  Inhibition of IKK-beta: a new development in the mechanism of the anti-obesity effects of PTP1B inhibitors SA18 and SA32.,  20  (3): [PMID:20044255] [10.1016/j.bmcl.2009.12.033]

Source

Source(1):

• Scientific Literature