[1-Hydroxy-2-(3-phenoxy-phenyl)-1-phosphono-ethyl]-phosphonic acid

ID: ALA425748

PubChem CID: 5277492

Max Phase: Preclinical

Molecular Formula: C14H16O8P2

Molecular Weight: 374.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(O)(Cc1cccc(Oc2ccccc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C14H16O8P2/c15-14(23(16,17)18,24(19,20)21)10-11-5-4-8-13(9-11)22-12-6-2-1-3-7-12/h1-9,15H,10H2,(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  XDTLXGCBLPCGID-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.4633  -25.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645  -26.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499  -27.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335  -26.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364  -25.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7517  -25.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238  -25.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183  -24.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115  -23.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431  -24.5816    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5065  -24.5901    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323  -24.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666  -24.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393  -23.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1481  -25.4064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151  -23.7653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967  -25.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777  -25.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920  -25.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6083  -25.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3220  -25.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3222  -26.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6028  -27.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921  -26.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
 10 14  1  0
  5  7  1  0
 10 15  1  0
  3  4  2  0
 11 16  1  0
  7  8  1  0
 11 17  1  0
  1 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
  8 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA425748

   [1-Hydroxy-2-(3-phenoxyphenyl)-1-phosphono-ethyl]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: 374.22

Molecular Weight (Monoisotopic): 374.0320

AlogP: 2.02

#Rotatable Bonds: 6

Polar Surface Area: 144.52

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 0.90

CX LogD: -4.04

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: -0.05

References

1. Kotsikorou E, Song Y, Chan JM, Faelens S, Tovian Z, Broderick E, Bakalara N, Docampo R, Oldfield E..  (2005)  Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase.,  48  (19): [PMID:16162013] [10.1021/jm058220g]

2. Song Y, Chan JM, Tovian Z, Secrest A, Nagy E, Krysiak K, Bergan K, Parniak MA, Oldfield E..  (2008)  Bisphosphonate inhibitors of ATP-mediated HIV-1 reverse transcriptase catalyzed excision of chain-terminating 3'-azido, 3'-deoxythymidine: a QSAR investigation.,  16  (19): [PMID:18789701] [10.1016/j.bmc.2008.08.047]

Source

Source(1):

• Scientific Literature