5-(3-Phenylsulfonylfuroxan-4-yloxy)pentylidenebis(phosphonic) acid

Names and Identifiers

Canonical SMILES: O=P(O)(O)C(CCCCOc1no[n+]([O-])c1S(=O)(=O)c1ccccc1)P(=O)(O)O

Standard InChI: InChI=1S/C13H18N2O11P2S/c16-15-13(29(23,24)10-6-2-1-3-7-10)12(14-26-15)25-9-5-4-8-11(27(17,18)19)28(20,21)22/h1-3,6-7,11H,4-5,8-9H2,(H2,17,18,19)(H2,20,21,22)

Standard InChI Key: UUOOWCLJIBYCCS-UHFFFAOYSA-N

Molfile:

     RDKit          2D

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   -2.7723  -16.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1198  -15.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005  -14.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242  -14.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798  -14.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0908  -13.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115  -12.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364  -12.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571  -11.9756    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407  -13.4044    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7310  -14.1648    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -13.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023  -13.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2919  -12.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988  -11.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199  -11.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265  -12.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500  -13.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333  -14.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 13 15  1  0
  2  3  1  0
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  7  8  1  0
 12 17  1  0
  3  4  2  0
 12 18  2  0
  8  9  1  0
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  4  5  1  0
  1 20  1  0
  9 10  1  0
  5 21  1  0
  5  1  2  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  1  2  1  0
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 11 12  1  0
 24 25  2  0
  4  6  1  0
 25 26  1  0
 11 13  1  0
 26 27  2  0
 27 22  1  0
 21 28  2  0
 13 14  2  0
 21 29  2  0
M  CHG  2   1   1  20  -1
M  END

Alternative Forms

Parent:

ALA1093436
[5-[[4-(Benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]-1-phosphonopentyl]phosphonic acid

Associated Targets(Human)

Hydroxyapatite (165 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Aorta (2975 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAW264.7 (28094 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 472.31	Molecular Weight (Monoisotopic): 472.0107	AlogP: 0.37	#Rotatable Bonds: 10
Polar Surface Area: 211.40	Molecular Species: ACID	HBA: 8	HBD: 4
#RO5 Violations: ┄	HBA (Lipinski): 13	HBD (Lipinski): 4	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 1.21	CX Basic pKa: ┄	CX LogP: -2.26	CX LogD: -6.92
Aromatic Rings: 2	Heavy Atoms: 29	QED Weighted: 0.21	Np Likeness Score: -0.58

References

1. Lolli ML, Rolando B, Tosco P, Chaurasia S, Di Stilo A, Lazzarato L, Gorassini E, Ferracini R, Oliaro-Bosso S, Fruttero R, Gasco A.. (2010) Synthesis and preliminary pharmacological characterisation of a new class of nitrogen-containing bisphosphonates (N-BPs)., 18 (7): [PMID:20299227] [10.1016/j.bmc.2010.02.058]

Source

Source(1):

Scientific Literature