[2-(3-Bromo-phenyl)-1-hydroxy-1-phosphono-ethyl]-phosphonic acid

ID: ALA371456

PubChem CID: 5277476

Max Phase: Preclinical

Molecular Formula: C8H11BrO7P2

Molecular Weight: 361.02

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C8H11BrO7P2/c9-7-3-1-2-6(4-7)5-8(10,17(11,12)13)18(14,15)16/h1-4,10H,5H2,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  YCSAMIGERDZRCB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   10.5134  -14.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2274  -14.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9414  -15.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6416  -13.9524    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.8132  -15.3833    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.3923  -16.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0499  -13.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3590  -14.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9233  -13.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5268  -15.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000  -14.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0855  -14.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -14.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3712  -15.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0835  -15.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7980  -15.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7951  -14.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6563  -14.2504    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
  1  2  1  0
  5 10  1  0
  2  5  1  0
  5 11  2  0
 17  1  1  0
  5  6  1  0
 12 13  2  0
  2  3  1  0
 13 14  1  0
  4  7  2  0
 14 15  2  0
 15 16  1  0
  4  8  1  0
 16 17  2  0
 17 12  1  0
  2  4  1  0
 13 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA371456

   [2-(3-Bromophenyl)-1-hydroxy-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: 361.02

Molecular Weight (Monoisotopic): 359.9163

AlogP: 0.99

#Rotatable Bonds: 4

Polar Surface Area: 135.29

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 0.21

CX LogD: -4.72

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.50

Np Likeness Score: -0.11

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. Leon A, Liu L, Yang Y, Hudock MP, Hall P, Yin F, Studer D, Puan KJ, Morita CT, Oldfield E..  (2006)  Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.,  49  (25): [PMID:17149863] [10.1021/jm060492b]

3. Mukkamala D, No JH, Cass LM, Chang TK, Oldfield E..  (2008)  Bisphosphonate inhibition of a Plasmodium farnesyl diphosphate synthase and a general method for predicting cell-based activity from enzyme data.,  51  (24): [PMID:19053772] [10.1021/jm8009074]

Source

Source(1):

• Scientific Literature