5,17-Bis[1-hydroxy-1,1-bis(dihydroxyphosphoryl)methyl]-25,27-dipropoxycalix[4]arene

ID: ALA2430578

PubChem CID: 73352369

Max Phase: Preclinical

Molecular Formula: C36H44O18P4

Molecular Weight: 888.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1c2cccc1Cc1cc(C(O)(P(=O)(O)O)P(=O)(O)O)cc(c1O)Cc1cccc(c1OCCC)Cc1cc(C(O)(P(=O)(O)O)P(=O)(O)O)cc(c1O)C2

Standard InChI:  InChI=1S/C36H44O18P4/c1-3-11-53-33-21-7-5-8-22(33)14-26-18-30(36(40,57(47,48)49)58(50,51)52)20-28(32(26)38)16-24-10-6-9-23(34(24)54-12-4-2)15-27-19-29(17-25(13-21)31(27)37)35(39,55(41,42)43)56(44,45)46/h5-10,17-20,37-40H,3-4,11-16H2,1-2H3,(H2,41,42,43)(H2,44,45,46)(H2,47,48,49)(H2,50,51,52)

Standard InChI Key:  WEUKZLZVXHNRLW-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2430578

   [[26,28-Dihydroxy-17-[hydroxy(diphosphono)methyl]-25,27-dipropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]-hydroxy-phosphonomethyl]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: 888.63

Molecular Weight (Monoisotopic): 888.1478

AlogP: 4.27

#Rotatable Bonds: 12

Polar Surface Area: 329.50

Molecular Species: ACID

HBA: 10

HBD: 12

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.31

CX Basic pKa: ┄

CX LogP: 3.71

CX LogD: -6.24

Aromatic Rings: 4

Heavy Atoms: 58

QED Weighted: 0.08

Np Likeness Score: 0.12

References

1. Trush VV, Cherenok SO, Tanchuk VY, Kukhar VP, Kalchenko VI, Vovk AI..  (2013)  Calix[4]arene methylenebisphosphonic acids as inhibitors of protein tyrosine phosphatase 1B.,  23  (20): [PMID:24012179] [10.1016/j.bmcl.2013.08.040]

Source

Source(1):

• Scientific Literature