2-[4'-(2-Benzyl-benzofuran-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid

ID: ALA365490

Chembl Id: CHEMBL365490

Cas Number: 250341-82-3

PubChem CID: 9914774

Max Phase: Preclinical

Molecular Formula: C36H28O4

Molecular Weight: 524.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](Cc1ccccc1)Oc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1

Standard InChI:  InChI=1S/C36H28O4/c37-36(38)34(24-26-11-5-2-6-12-26)39-30-21-19-28(20-22-30)27-15-17-29(18-16-27)35-31-13-7-8-14-32(31)40-33(35)23-25-9-3-1-4-10-25/h1-22,34H,23-24H2,(H,37,38)/t34-/m0/s1

Standard InChI Key:  CBAKPPAEHFOGJA-UMSFTDKQSA-N

Alternative Forms

1. Parent:

   

   ALA365490

   (2S)-2-[4'-(2-Benzyl-benzofuran-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic 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: 524.62

Molecular Weight (Monoisotopic): 524.1988

AlogP: 8.43

#Rotatable Bonds: 9

Polar Surface Area: 59.67

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.94

CX Basic pKa: ┄

CX LogP: 8.83

CX LogD: 5.63

Aromatic Rings: 6

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: 0.16

References

1. Malamas MS, Sredy J, Moxham C, Katz A, Xu W, McDevitt R, Adebayo FO, Sawicki DR, Seestaller L, Sullivan D, Taylor JR..  (2000)  Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties.,  43  (7): [PMID:10753467] [10.1021/jm990560c]

2. Yang C, Cross K, Myatt GJ, Blower PE, Rathman JF..  (2004)  Building predictive models for protein tyrosine phosphatase 1B inhibitors based on discriminating structural features by reassembling medicinal chemistry building blocks.,  47  (24): [PMID:15537353] [10.1021/jm0497242]

3. Cheng Y, Zhou M, Tung CH, Ji M, Zhang F..  (2010)  Studies on two types of PTP1B inhibitors for the treatment of type 2 diabetes: Hologram QSAR for OBA and BBB analogues.,  20  (11): [PMID:20452766] [10.1016/j.bmcl.2010.04.033]

4. Kousaxidis A, Petrou A, Lavrentaki V, Fesatidou M, Nicolaou I, Geronikaki A..  (2020)  Aldose reductase and protein tyrosine phosphatase 1B inhibitors as a promising therapeutic approach for diabetes mellitus.,  207  [PMID:32871344] [10.1016/j.ejmech.2020.112742]

Source

Source(1):

• Scientific Literature