hydrogen 1-hydroxy-2-(3-methylpyridinium-1-yl)-1-phosphonoethylphosphonate

ID: ALA193356

PubChem CID: 11335461

Max Phase: Preclinical

Molecular Formula: C8H13NO7P2

Molecular Weight: 297.14

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1ccc[n+](CC(O)(P(=O)([O-])O)P(=O)(O)O)c1

Standard InChI:  InChI=1S/C8H13NO7P2/c1-7-3-2-4-9(5-7)6-8(10,17(11,12)13)18(14,15)16/h2-5,10H,6H2,1H3,(H3-,11,12,13,14,15,16)

Standard InChI Key:  WNMNDCTVXVBAFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.0042   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    0.1750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -1.0625    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -0.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042    0.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -1.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  5  1  1  0
  6  2  1  0
  7  2  2  0
  8  3  2  0
  9  1  1  0
 10  4  2  0
 11  2  1  0
 12  3  1  0
 13  3  1  0
 14  4  1  0
 15 10  1  0
 16 14  2  0
 17 16  1  0
 18 15  1  0
 17 15  2  0
M  CHG  2   4   1   6  -1
M  END

Associated Targets(Human)

MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Farnesyl pyrophosphate synthase (85 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dictyostelium discoideum (81 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ispH 4-hydroxy-3-methylbut-2-enyl diphosphate reductase (23 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 297.14Molecular Weight (Monoisotopic): 297.0167AlogP: -1.35#Rotatable Bonds: 4
Polar Surface Area: 142.00Molecular Species: ACIDHBA: 4HBD: 4
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 0.59CX Basic pKa: CX LogP: -5.32CX LogD: -9.11
Aromatic Rings: 1Heavy Atoms: 18QED Weighted: 0.40Np Likeness Score: 0.11

References

1. Sanders JM, Song Y, Chan JM, Zhang Y, Jennings S, Kosztowski T, Odeh S, Flessner R, Schwerdtfeger C, Kotsikorou E, Meints GA, Gómez AO, González-Pacanowska D, Raker AM, Wang H, van Beek ER, Papapoulos SE, Morita CT, Oldfield E..  (2005)  Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption.,  48  (8): [PMID:15828834] [10.1021/jm040209d]
2. Zhang Y, Leon A, Song Y, Studer D, Haase C, Koscielski LA, Oldfield E..  (2006)  Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines.,  49  (19): [PMID:16970405] [10.1021/jm060280e]
3. 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]

Source