5-(2-amino-5-(phenylthio)oxazol-4-yl)furan-2-ylphosphonic acid

Names and Identifiers

Canonical SMILES: Nc1nc(-c2ccc(P(=O)(O)O)o2)c(Sc2ccccc2)o1

Standard InChI: InChI=1S/C13H11N2O5PS/c14-13-15-11(9-6-7-10(19-9)21(16,17)18)12(20-13)22-8-4-2-1-3-5-8/h1-7H,(H2,14,15)(H2,16,17,18)

Standard InChI Key: IBIJSTSDYCGVJN-UHFFFAOYSA-N

Molfile:

     RDKit          2D

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    8.2709   -5.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5253   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8623   -4.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2036   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3028   -4.3414    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.9094   -4.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8901   -3.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8806   -3.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4263   -4.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720   -3.5666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3539   -3.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026   -4.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -4.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728   -2.9062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7693   -5.6412    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631   -6.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -5.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499   -6.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6525   -6.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -7.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -6.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 11 12  2  0
 10 11  1  0
 12 13  1  0
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 16 17  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

Parent:

ALA3217761
[5-(2-Amino-5-phenylsulfanyl-1,3-oxazol-4-yl)furan-2-yl]phosphonic acid

Associated Targets(Human)

FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

Discover Target: FBP1

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

Associated Targets(non-human)

Fbp1 Fructose-1,6-bisphosphatase (106 Activities)

Discover Target: Fbp1

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

Rattus norvegicus (775804 Activities)

Explore this target

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: 338.28	Molecular Weight (Monoisotopic): 338.0126	AlogP: 2.47	#Rotatable Bonds: 4
Polar Surface Area: 122.72	Molecular Species: ACID	HBA: 6	HBD: 3
#RO5 Violations: ┄	HBA (Lipinski): 7	HBD (Lipinski): 4	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 1.30	CX Basic pKa: 0.40	CX LogP: 1.57	CX LogD: -1.42
Aromatic Rings: 3	Heavy Atoms: 22	QED Weighted: 0.62	Np Likeness Score: -0.48

References

1. Dang Q, Kasibthatla SR, Jiang T, Taplin F, Gibson T, Potter SC, van Poelje PD, Erion MD. (2011) Oxazole phosphonic acids as fructose 1,6-bisphosphatase inhibitors with potent glucose-lowering activity, 2 (4): [10.1039/C0MD00269K]

Source

Source(1):

Scientific Literature