Page last updated: 2024-12-05

hadacidin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hadacidin is a naturally occurring nucleoside analog that inhibits the biosynthesis of purines and pyrimidines. It is produced by the bacterium *Nocardia *species. Hadacidin acts as a substrate analog for the enzyme formyltetrahydrofolate reductase, which is involved in the synthesis of tetrahydrofolic acid, an essential cofactor for many metabolic reactions. By inhibiting this enzyme, Hadacidin blocks the production of purine and pyrimidine nucleotides, which are essential building blocks for DNA and RNA. Hadacidin has been studied for its potential anticancer activity. Its ability to inhibit DNA and RNA synthesis suggests that it might be effective against rapidly dividing cancer cells. However, its clinical use is limited due to its toxicity. Hadacidin has also been used as a tool to study the role of purine and pyrimidine metabolism in various biological processes. It has been used to investigate the regulation of cell growth and proliferation, as well as the mechanisms of DNA damage and repair.'

hadacidin: inhibitor of AMP synthesis; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

hadacidin : A monocarboxylic acid that is N-hydroxyglycine in which the hydrogen attached to the nitrogen is replaced by a formyl group. It was originally isolated from cultures of Penicillium frequentans. [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]

Cross-References

ID SourceID
PubMed CID12717
CHEMBL ID331373
CHEBI ID43040
SCHEMBL ID2115651
MeSH IDM0041456

Synonyms (36)

Synonym
nsc-72962
(formyl-hydroxy-amino)-acetic acid
bdbm50149248
NCI60_004270
nsc 72962
n-formyl-n-hydroxyglycine
asymmetrin
brn 1927168
nfhaa
hadacin
glycine, n-formyl-n-hydroxy-
hadacidin
nsc-521778
hadacidine
n-hydroxyformamidoacetic acid
n-formyl hydroxyaminoacetic acid
n-formyl-n- hydroxyaminoacetic acid
DB02109
2-[formyl(hydroxy)amino]acetic acid
CHEMBL331373 ,
chebi:43040 ,
AKOS006278464
689-13-4
bfo5p1010a ,
unii-bfo5p1010a
[formyl(hydroxy)amino]acetic acid
n-formyl-n-hydroxyaminoacetic acid
hadacidin [mi]
DTXSID1043962
SCHEMBL2115651
2-(n-hydroxyformamido)acetic acid
Q15303927
BCP31244
asymmetrin; hadacidin
2-(n-hydroxyformamido)aceticacid
A917433

Research Excerpts

Treatment

Hadacidin treatment affected DNA synthesis in the developing primordia of the palate. Treatment with hadacidin also affected the intracellular content of these enzyme activities.

ExcerptReferenceRelevance
"Hadacidin treatment also affected DNA synthesis in the developing primordia of the palate."( Genesis of hadacidin-induced cleft palate in hamster: morphogenesis, electron microscopy, and determination of DNA synthesis, cAMP, and enzyme acid phosphatase.
Benkhaial, G; Burdett, D; Schuing, R; Shah, RM; Young, AV, 1991
)
1.39
"Treatment with hadacidin also affected the intracellular content of these enzyme activities."( Lysosomal abnormalities in hadacidin-treated Dictyostelium discoideum amoebae.
Crean, EV; Lagerstedt, JP; Rossomando, EF, 1981
)
0.9
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
teratogenic agentA role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Penicillium metaboliteAny fungal metabolite produced during a metabolic reaction in Penicillium.
[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]

Drug Classes (3)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy group.
N-hydroxy-alpha-amino-acidAny amino acid in which at least one hydrogen attached to the amino group is replaced by a hydroxy group.
aldehydeA compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.
[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 Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenylosuccinate synthetase isozyme 2Homo sapiens (human)IC50 (µMol)3.50003.50003.50003.5000AID32784
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
immune system processAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
AMP biosynthetic processAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
aspartate metabolic processAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
response to purine-containing compoundAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
'de novo' AMP biosynthetic processAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
response to ammonium ionAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
cellular response to electrical stimulusAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
IMP metabolic processAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
magnesium ion bindingAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
adenylosuccinate synthase activityAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
protein bindingAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
GTP bindingAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
phosphate ion bindingAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrionAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
cytosolAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
extracellular exosomeAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
cytoplasmAdenylosuccinate synthetase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID409947Inhibition of human recombinant MAOB at 1 mM by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID549687Inhibition of adenylosuccinate synthase at 10 mM2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Evaluation of hadacidin analogues.
AID409952Inhibition of human brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID549685Inhibition of adenylosuccinate synthase at 5:1 aspartate to compound ratio2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Evaluation of hadacidin analogues.
AID549686Inhibition of adenylosuccinate synthase at 1:1 aspartate to compound ratio2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
Evaluation of hadacidin analogues.
AID32784Inhibitory concentration against Adenylosuccinate synthetase2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Fragment-based drug discovery.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199037 (58.73)18.7374
1990's16 (25.40)18.2507
2000's5 (7.94)29.6817
2010's4 (6.35)24.3611
2020's1 (1.59)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.69

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.69 (24.57)
Research Supply Index4.16 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.69)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.59%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other62 (98.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]