Compounds > mb 05032
Page last updated: 2024-10-14

mb 05032

Cross-References

ID SourceID
PubMed CID11289630
CHEMBL ID495498
SCHEMBL ID2742711
MeSH IDM0551360

Synonyms (31)

Synonym
CHEMBL495498 ,
mb-05032 ,
mb05032 ,
261365-11-1
F9995-0175
[5-(2-amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid
5-(2-amino-5-isobutylthiazol-4-yl)furan-2-ylphosphonic acid
bdbm50293594
AKOS015957645
HY-16307
CS-1552
SCHEMBL2742711
c11h15n2o4ps
VU0549312-1
(5-(2-amino-5-isobutylthiazol-4-yl)furan-2-yl)phosphonic acid
[5-[2-amino-5-(2-methylpropyl)-thiazol-4-yl]-furan-2-yl]-phosphonic acid
XJMYIJPPDSZOPN-UHFFFAOYSA-N
{5-[2-amino-5-(2-methylpropyl)-1,3-thiazol-4-yl]furan-2-yl}phosphonic acid
94d ,
unii-9379mh4cal
[5-[2-amino-5-(2-methylpropyl)-1,3-thiazol-4-yl]furan-2-yl]phosphonic acid
p-[5-[2-amino-5-(2-methylpropyl)-4-thiazolyl]-2-furanyl]phosphonic acid
mb 05032
phosphonic acid, p-[5-[2-amino-5-(2-methylpropyl)-4-thiazolyl]-2-furanyl]-
p-(5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)phosphonic acid
(5-(2-amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl)phosphonic acid
phosphonic acid, (5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)-
2-amino-5-isobutyl-4-(5-phosphono-2-furanyl)thiazole
9379MH4CAL ,
F84965
EN300-238163

Bioavailability

ExcerptReference
"Like most phosphonic acids, the recently discovered potent and selective thiazole phosphonic acid inhibitors of fructose 1,6-bisphosphatase (FBPase) exhibited low oral bioavailability (OBAV) and therefore required a prodrug to achieve oral efficacy."( Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors.
Cashion, DK; Dang, Q; Erion, MD; Fan, K; Fujitaki, JM; Jiang, T; Kasibhatla, SR; Liu, Y; Potter, SC; Reddy, KR; Schulz, W; Taplin, F; van Poelje, PD, 2008)
" Various phosphonate prodrugs were explored without success, until a novel phosphonic diamide prodrug approach was implemented, which delivered compound 30j with good oral bioavailability (OBAV) (22-47%)."( Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
Cashion, DK; Dang, Q; DaRe, J; Erion, MD; Fan, Y; Gibson, T; Jacintho, JD; Jiang, T; Kasibhatla, SR; Lemus, R; Li, H; Li, W; Liu, Y; Potter, SC; Sun, Z; Taplin, F; Tian, F; van Poelje, PD, 2011)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)0.01600.00001.559910.0000AID443979
Fructose-1,6-bisphosphatase 1Homo sapiens (human)IC50 (µMol)0.02170.01002.00979.8000AID1723958; AID1724003; AID443979; AID446447; AID461157; AID554209
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fructose-1,6-bisphosphatase 1Homo sapiens (human)EC50 (µMol)0.01600.01600.01600.0160AID419857
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fructose-1,6-bisphosphatase 1Homo sapiens (human)Activity0.01600.01600.01600.0160AID344063
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIFructose-1,6-bisphosphatase 1Homo sapiens (human)
fructose 6-phosphate metabolic processFructose-1,6-bisphosphatase 1Homo sapiens (human)
gluconeogenesisFructose-1,6-bisphosphatase 1Homo sapiens (human)
regulation of gluconeogenesisFructose-1,6-bisphosphatase 1Homo sapiens (human)
dephosphorylationFructose-1,6-bisphosphatase 1Homo sapiens (human)
negative regulation of cell growthFructose-1,6-bisphosphatase 1Homo sapiens (human)
response to nutrient levelsFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to insulin stimulusFructose-1,6-bisphosphatase 1Homo sapiens (human)
negative regulation of glycolytic processFructose-1,6-bisphosphatase 1Homo sapiens (human)
negative regulation of Ras protein signal transductionFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to magnesium ionFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to cAMPFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to xenobiotic stimulusFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular hyperosmotic salinity responseFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular hypotonic salinity responseFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to raffinoseFructose-1,6-bisphosphatase 1Homo sapiens (human)
cellular response to phorbol 13-acetate 12-myristateFructose-1,6-bisphosphatase 1Homo sapiens (human)
fructose 1,6-bisphosphate metabolic processFructose-1,6-bisphosphatase 1Homo sapiens (human)
fructose metabolic processFructose-1,6-bisphosphatase 1Homo sapiens (human)
sucrose biosynthetic processFructose-1,6-bisphosphatase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
protein bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
AMP bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
fructose 1,6-bisphosphate 1-phosphatase activityFructose-1,6-bisphosphatase 1Homo sapiens (human)
identical protein bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
metal ion bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
monosaccharide bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingFructose-1,6-bisphosphatase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
nucleusFructose-1,6-bisphosphatase 1Homo sapiens (human)
cytoplasmFructose-1,6-bisphosphatase 1Homo sapiens (human)
cytosolFructose-1,6-bisphosphatase 1Homo sapiens (human)
extracellular exosomeFructose-1,6-bisphosphatase 1Homo sapiens (human)
cytoplasmFructose-1,6-bisphosphatase 1Homo sapiens (human)
cytosolFructose-1,6-bisphosphatase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1723958Inhibition of human liver FBPase expressed in Escherichia coli BL21(DE3) using FBP as substrate in presence of PGI and G6PDH by spectrophotometric method2020Journal of medicinal chemistry, 09-24, Volume: 63, Issue:18
Discovery of
AID344063Inhibition of human fructose-1,6-bisphosphatase2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors.
AID344060Half life in cryopreserved human hepatocytes at 100 uM2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors.
AID554216Oral bioavailability in Sprague-Dawley rat2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID419857Inhibition of human liver FBPase2009Bioorganic & medicinal chemistry, Jun-01, Volume: 17, Issue:11
A library of novel allosteric inhibitors against fructose 1,6-bisphosphatase.
AID554209Inhibition of human liver FBP2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID1724003Inhibition of human liver FBPase expressed in Escherichia coli by spectrophotometric method2020Journal of medicinal chemistry, 09-24, Volume: 63, Issue:18
Discovery of
AID344058Reduction in blood glucose level in fasted Sprague-Dawley rat at <=10 mg/kg, iv relative to control2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors.
AID554213Volume of distribution in Sprague-Dawley rat2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID344055Bioavailability in fasted Sprague-Dawley rat assessed as urinary excretion of phosphoric acid at 10 to 50 mg/kg, po after 24 hrs by HPLC relative to iv dosed phosphoric acid2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors.
AID461157Inhibition of human liver recombinant FBPase2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors.
AID443979Inhibition of human liver FBPase 12010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Fructose-1,6-bisphosphatase Inhibitors. 2. Design, synthesis, and structure-activity relationship of a series of phosphonic acid containing benzimidazoles that function as 5'-adenosinemonophosphate (AMP) mimics.
AID446447Inhibition of human liver FBPase2009Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20
Synthesis, SAR, and X-ray structure of tricyclic compounds as potent FBPase inhibitors.
AID554214Plasma protein binding in Sprague-Dawley rat2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID554212Clearance in Sprague-Dawley rat2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID554215Plasma protein binding in human2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID554211Half life in Sprague-Dawley rat2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
AID1859317Inhibition of recombinant human FBP expressed in expressed Escherichia coli BL21 (DE3) incubated for 1 hr by hanging drop vapour method2022ACS medicinal chemistry letters, Jan-13, Volume: 13, Issue:1
Discovery of Novel Indole Derivatives as Fructose-1,6-bisphosphatase Inhibitors and X-ray Cocrystal Structures Analysis.
AID554210Antidiabetic activity in Sprague-Dawley rat assessed as decrease in glucose Cmax at 10 mg/kg, iv2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (37.50)29.6817
2010's3 (37.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		2.8430adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
phenthiazamine
phenthiazamine: RN given refers to parent cpd		2.0510
4-(2-Amino-1,3-thiazol-4-yl)phenol
[no description available]		2.0510phenols
4-[(4-phenyl-2-thiazolyl)amino]benzenesulfonamide
[no description available]		2.0510sulfonamide
gs-7340
tenofovir alafenamide: component of Biktarvy. tenofovir alafenamide : An L-alanine derivative that is isopropyl L-alaninate in which one of the amino hydrogens is replaced by an (S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl group. A prodrug for tenofovir, it is used (as the fumarate salt) in combination therapy for the treatment of HIV-1 infection.		2.04106-aminopurines;
ether;
isopropyl ester;
L-alanine derivative;
phosphoramidate ester		antiviral drug;
HIV-1 reverse transcriptase inhibitor;
prodrug
n,n'-((5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)phosphinylidene)bis(alanine) diethyl ester
N,N'-((5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)phosphinylidene)bis(alanine) diethyl ester: structure in first source		2.4620
ConditionIndicatedRelationship StrengthStudiesTrials
Diabetes Mellitus, Adult-Onset
[description not available]		02.4620
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0510
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		14.4620
Alloxan Diabetes
[description not available]		02.0610
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		02.2510