phosphoglycolohydroxamate profile

Phosphoglycolohydroxamate (PGH) is a synthetic compound that acts as a potent inhibitor of various enzymes involved in the biosynthesis of purines and pyrimidines. It is known to inhibit the activity of glycinamide ribonucleotide formyltransferase (GARFT), an essential enzyme in the purine biosynthesis pathway. PGH's inhibitory effect on GARFT is highly specific and has been shown to effectively block the production of purines. This inhibition leads to a depletion of cellular nucleotide pools, ultimately hindering cell growth and proliferation. Studies on PGH have focused on its potential as an anti-cancer agent due to its ability to target key metabolic pathways involved in tumor cell growth and survival. The compound's mechanism of action, its selectivity for GARFT, and its impact on purine biosynthesis make it an intriguing target for further research in the development of novel cancer therapies.'

phosphoglycolohydroxamate: inhibits DHAP (dihydroxyacetone phosphate)-converting enzymes; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phosphoglycolohydroxamic acid : The hydroxamate of phosphoglycolic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	4797
CHEMBL ID	371668
CHEBI ID	28475
SCHEMBL ID	4309631
MeSH ID	M0053127

Synonym
acetamide, n-hydroxy-2-(phosphonooxy)-
PGH ,
phosphoglycolohydroxamic acid
1TRD
1IK4
DB02739
1TPW ,
DB03026
phosphoglycolohydroxamate
2-(hydroxyamino)-2-oxoethyl dihydrogen phosphate
CHEBI:28475 ,
51528-59-7
bdbm50167777
CHEMBL371668 ,
phosphoric acid monohydroxycarbamoylmethyl ester
SCHEMBL4309631
DTXSID90199497
Q27093998
2-(hydroxyamino)-2-oxoethyldihydrogenphosphate
[(hydroxycarbamoyl)methoxy]phosphonic acid
HY-148077
CS-0610369

Role	Description
EC 5.3.1.1 (triose-phosphate isomerase) inhibitor	Any EC 5.3.1.* (intramolecular oxidoreductase interconverting aldoses and ketoses) inhibitor that interferes with the action of a triose-phosphate isomerase (EC 5.3.1.1).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
amidoalkyl phosphate
hydroxamic acid	A compound, RkE(=O)lNHOH, derived from an oxoacid RkE(=O)l(OH) (l =/= 0) by replacing -OH with -NHOH, and derivatives thereof. Specific examples of hydroxamic acids are preferably named as N-hydroxy amides.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Methylglyoxal Synthase	Escherichia coli	Ki	0.0390	0.0390	0.0390	0.0390	AID977610
Chain F, Methylglyoxal Synthase	Escherichia coli	Ki	0.0390	0.0390	0.0390	0.0390	AID977610
Chain B, TRIOSEPHOSPHATE ISOMERASE	Trypanosoma brucei brucei	Ki	4.0000	4.0000	4.0000	4.0000	AID977610
Fructose-bisphosphate aldolase A	Oryctolagus cuniculus (rabbit)	Ki	1.0000	1.0000	1.0000	1.0000	AID257659
Fructose-bisphosphate aldolase class 2	Escherichia coli K-12	Ki	0.0100	0.0100	0.0100	0.0100	AID257660
Triosephosphate isomerase	Homo sapiens (human)	Ki	3.5000	3.0000	3.5000	4.0000	AID292822; AID594834
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
glycolytic process	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
glycolytic process	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
gluconeogenesis	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
gluconeogenesis	Triosephosphate isomerase	Homo sapiens (human)
methylglyoxal biosynthetic process	Triosephosphate isomerase	Homo sapiens (human)
glyceraldehyde-3-phosphate biosynthetic process	Triosephosphate isomerase	Homo sapiens (human)
canonical glycolysis	Triosephosphate isomerase	Homo sapiens (human)
glycolytic process	Triosephosphate isomerase	Homo sapiens (human)
glycerol catabolic process	Triosephosphate isomerase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
fructose-bisphosphate aldolase activity	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
protein binding	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
zinc ion binding	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
lyase activity	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
identical protein binding	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
protein homodimerization activity	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
metal ion binding	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
triose-phosphate isomerase activity	Triosephosphate isomerase	Homo sapiens (human)
protein binding	Triosephosphate isomerase	Homo sapiens (human)
methylglyoxal synthase activity	Triosephosphate isomerase	Homo sapiens (human)
ubiquitin protein ligase binding	Triosephosphate isomerase	Homo sapiens (human)
protein homodimerization activity	Triosephosphate isomerase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
cytosol	Fructose-bisphosphate aldolase class 2	Escherichia coli K-12
extracellular space	Triosephosphate isomerase	Homo sapiens (human)
nucleus	Triosephosphate isomerase	Homo sapiens (human)
cytosol	Triosephosphate isomerase	Homo sapiens (human)
extracellular exosome	Triosephosphate isomerase	Homo sapiens (human)
cytosol	Triosephosphate isomerase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay ID	Title	Year	Journal	Article
AID1811	Experimentally measured binding affinity data derived from PDB	2001	Biochemistry, Jun-12, Volume: 40, Issue:23	Mechanistic implications of methylglyoxal synthase complexed with phosphoglycolohydroxamic acid as observed by X-ray crystallography and NMR spectroscopy.
AID977610	Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	2001	Biochemistry, Jun-12, Volume: 40, Issue:23	Mechanistic implications of methylglyoxal synthase complexed with phosphoglycolohydroxamic acid as observed by X-ray crystallography and NMR spectroscopy.
AID292822	Inhibition of triosephosphate isomerase	2007	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2	New competitive inhibitors of cytosolic (NADH-dependent) rabbit muscle glycerophosphate dehydrogenase.
AID68946	Selectivity (Ki rabbit /Ki yeast) of inhibitors for class II versus class I FBP aldolase	2004	Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11	New highly selective inhibitors of class II fructose-1,6-bisphosphate aldolases.
AID292820	Inhibition of class I FBA	2007	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2	New competitive inhibitors of cytosolic (NADH-dependent) rabbit muscle glycerophosphate dehydrogenase.
AID68939	In vitro binding affinity towards FBP aldolase from yeast	2004	Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11	New highly selective inhibitors of class II fructose-1,6-bisphosphate aldolases.
AID257659	Inhibitory activity against class I FBP aldolase from rabbit	2005	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24	N-Sulfonyl hydroxamate derivatives as inhibitors of class II fructose-1,6-diphosphate aldolase.
AID257660	Inhibitory activity against class II FBP aldolase from Escherichia coli	2005	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24	N-Sulfonyl hydroxamate derivatives as inhibitors of class II fructose-1,6-diphosphate aldolase.
AID238281	Binding affinity against class II fructose-bisphosphate aldolase	2005	Bioorganic & medicinal chemistry letters, Jun-02, Volume: 15, Issue:11	New inhibitors of rabbit muscle triose-phosphate isomerase.
AID292821	Inhibition of class II FBA	2007	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2	New competitive inhibitors of cytosolic (NADH-dependent) rabbit muscle glycerophosphate dehydrogenase.
AID68942	In vitro binding towards FBP aldolase from rabbit	2004	Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11	New highly selective inhibitors of class II fructose-1,6-bisphosphate aldolases.
AID594834	Inhibition of Triosephosphate isomerase	2011	Bioorganic & medicinal chemistry letters, May-01, Volume: 21, Issue:9	Enediol mimics as inhibitors of the D-arabinose 5-phosphate isomerase (KdsD) from Francisella tularensis.
AID292823	Inhibition of rabbit muscle NADH-dependent cytosolic glycerophosphate dehydrogenase	2007	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2	New competitive inhibitors of cytosolic (NADH-dependent) rabbit muscle glycerophosphate dehydrogenase.
AID238454	Binding affinity against rabbit muscle triose-phosphate isomerase	2005	Bioorganic & medicinal chemistry letters, Jun-02, Volume: 15, Issue:11	New inhibitors of rabbit muscle triose-phosphate isomerase.
AID1811	Experimentally measured binding affinity data derived from PDB	1993	Proteins, Aug, Volume: 16, Issue:4	Structures of the "open" and "closed" state of trypanosomal triosephosphate isomerase, as observed in a new crystal form: implications for the reaction mechanism.
AID977610	Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	1993	Proteins, Aug, Volume: 16, Issue:4	Structures of the "open" and "closed" state of trypanosomal triosephosphate isomerase, as observed in a new crystal form: implications for the reaction mechanism.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.57)	18.7374
1990's	10 (35.71)	18.2507
2000's	9 (32.14)	29.6817
2010's	8 (28.57)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	6.95	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
phosphoglycolate phosphoglycolate: RN given refers to parent acid. 2-phosphoglycolic acid : The O-phospho derivative of glycolic acid.	2.7	3	carboxyalkyl phosphate	Escherichia coli metabolite; mouse metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	3.53	8	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	1.99	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2	1	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.68	3	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
fructose-1,6-diphosphate beta-D-fructofuranose 1,6-bisphosphate : A D-fructofuranose 1,6-bisphosphate with a beta-configuration at the anomeric position.	2.02	1	D-fructofuranose 1,6-bisphosphate	mouse metabolite
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.01	1	dihydrogen
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.4	2	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
4-phospho-d-erythronohydroxamic acid [no description available]	2.06	1
4-phosphoerythronate 4-phosphoerythronate: inhibits ribose-5-phosphate isomerase. 4-phospho-D-erythronic acid : The D-enantiomer of 4-phosphoerythronic acid.	2.06	1	4-phosphoerythronic acid	Escherichia coli metabolite; mouse metabolite
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	1.98	1	ammonium salt; inorganic sulfate salt	fertilizer

phosphoglycolohydroxamate

Description

Cross-References

Synonyms (22)

Roles (1)

Drug Classes (2)

Protein Targets (6)

Inhibition Measurements

Biological Processes (6)

Molecular Functions (10)

Ceullar Components (4)

Bioassays (16)

Research

Studies (28)

Market Indicators

Research Demand Index: 12.10

Study Types

phosphoglycolohydroxamate

Description

Cross-References

Synonyms (22)

Roles (1)

Drug Classes (2)

Protein Targets (6)

Inhibition Measurements

Biological Processes (6)

Molecular Functions (10)

Ceullar Components (4)

Bioassays (16)

Research

Studies (28)

Market Indicators

Research Demand Index: 12.10

Study Types

Related Drugs (13)

Related Conditions (0)