[(4-{4-[4-(Difluoro-phosphono-methyl)-benzyloxy]-phenoxymethyl}-phenyl)-difluoro-methyl]-phosphonic acid

ID: ALA140954

Chembl Id: CHEMBL140954

PubChem CID: 10256983

Max Phase: Preclinical

Molecular Formula: C22H20F4O8P2

Molecular Weight: 550.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(F)(F)c1ccc(COc2ccc(OCc3ccc(C(F)(F)P(=O)(O)O)cc3)cc2)cc1

Standard InChI:  InChI=1S/C22H20F4O8P2/c23-21(24,35(27,28)29)17-5-1-15(2-6-17)13-33-19-9-11-20(12-10-19)34-14-16-3-7-18(8-4-16)22(25,26)36(30,31)32/h1-12H,13-14H2,(H2,27,28,29)(H2,30,31,32)

Standard InChI Key:  ISVHAWKFOXJXLZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA140954

   [(4-{4-[4-(Difluoro-phosphono-methyl)-benzyloxy]-phenoxymethyl}-phenyl)-difluoro-methyl]-phosphonic 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: 550.33

Molecular Weight (Monoisotopic): 550.0570

AlogP: 5.30

#Rotatable Bonds: 10

Polar Surface Area: 133.52

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.19

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: -1.82

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: -0.27

References

1. Jia Z, Ye Q, Dinaut AN, Wang Q, Waddleton D, Payette P, Ramachandran C, Kennedy B, Hum G, Taylor SD..  (2001)  Structure of protein tyrosine phosphatase 1B in complex with inhibitors bearing two phosphotyrosine mimetics.,  44  (26): [PMID:11741477] [10.1021/jm010266w]

Source

Source(1):

• Scientific Literature