(1-Phosphono-2-pyridin-3-yl-ethyl)-phosphonic acid

ID: ALA98110

Cas Number: 75755-10-1

PubChem CID: 10468166

Product Number: D134844, Order Now?

Max Phase: Preclinical

Molecular Formula: C7H11NO6P2

Molecular Weight: 267.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Cc1cccnc1)P(=O)(O)O

Standard InChI:  InChI=1S/C7H11NO6P2/c9-15(10,11)7(16(12,13)14)4-6-2-1-3-8-5-6/h1-3,5,7H,4H2,(H2,9,10,11)(H2,12,13,14)

Standard InChI Key:  KZMOFWIRXNQJET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   11.5982   -4.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3122   -5.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3115   -6.0904    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0269   -4.8526    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.7383   -4.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4382   -5.5663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6082   -4.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3098   -6.9081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1357   -6.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4872   -6.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8834   -5.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1736   -4.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594   -5.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4582   -6.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1772   -6.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8885   -6.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  1  0
  4  5  1  0
  3 10  2  0
  2  3  1  0
  1 11  1  0
  4  6  1  0
 11 12  2  0
  1  2  1  0
 12 13  1  0
  4  7  2  0
 13 14  2  0
  2  4  1  0
 14 15  1  0
  3  8  1  0
 15 16  2  0
 16 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA98110

   Deoxy Risedronic 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: 267.11

Molecular Weight (Monoisotopic): 267.0062

AlogP: 0.31

#Rotatable Bonds: 4

Polar Surface Area: 127.95

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.20

CX Basic pKa: 4.93

CX LogP: -3.64

CX LogD: -6.40

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.58

Np Likeness Score: -0.29

References

1. Szabo CM, Martin MB, Oldfield E..  (2002)  An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs.,  45  (14): [PMID:12086477] [10.1021/jm010279+]

2. Sanders JM, Ghosh S, Chan JM, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E..  (2004)  Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.,  47  (2): [PMID:14711309] [10.1021/jm0303709]

3. Marma MS, Xia Z, Stewart C, Coxon F, Dunford JE, Baron R, Kashemirov BA, Ebetino FH, Triffitt JT, Russell RG, McKenna CE..  (2007)  Synthesis and biological evaluation of alpha-halogenated bisphosphonate and phosphonocarboxylate analogues of risedronate.,  50  (24): [PMID:17975902] [10.1021/jm0702884]

4. Dunford JE, Kwaasi AA, Rogers MJ, Barnett BL, Ebetino FH, Russell RG, Oppermann U, Kavanagh KL..  (2008)  Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.,  51  (7): [PMID:18327899] [10.1021/jm7015733]

5. K-M Chen C, Hudock MP, Zhang Y, Guo RT, Cao R, No JH, Liang PH, Ko TP, Chang TH, Chang SC, Song Y, Axelson J, Kumar A, Wang AH, Oldfield E..  (2008)  Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation.,  51  (18): [PMID:18800762] [10.1021/jm800325y]

6. Wang K, Wang W, No JH, Zhang Y, Zhang Y, Oldfield E..  (2010)  Inhibition of the Fe(4)S(4)-cluster-containing protein IspH (LytB): electron paramagnetic resonance, metallacycles, and mechanisms.,  132  (19): [PMID:20426416] [10.1021/ja909664j]

7. De Schutter JW, Park J, Leung CY, Gormley P, Lin YS, Hu Z, Berghuis AM, Poirier J, Tsantrizos YS..  (2014)  Multistage screening reveals chameleon ligands of the human farnesyl pyrophosphate synthase: implications to drug discovery for neurodegenerative diseases.,  57  (13): [PMID:24911527] [10.1021/jm500629e]

Source

Source(1):

• Scientific Literature