Page last updated: 2024-12-04

5,6-dihydroorotate

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

Description

5,6-Dihydroorotate is a key intermediate in the biosynthesis of pyrimidine nucleotides, which are essential building blocks of DNA and RNA. It is formed by the reduction of orotate by the enzyme dihydroorotate dehydrogenase. This compound has been studied for its potential therapeutic applications in various conditions, including cancer and autoimmune diseases. For instance, 5,6-dihydroorotate has shown anti-proliferative effects in certain cancer cell lines by inhibiting the enzyme ribonucleotide reductase, which is involved in DNA synthesis. It is also being investigated for its potential to modulate the immune response and treat autoimmune diseases.'

4,5-dihydroorotic acid: RN given refers to cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dihydroorotic acid : A pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N(alpha)-carbethoxyasparagine. [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 CID648
CHEMBL ID75782
CHEBI ID30865
SCHEMBL ID121953
MeSH IDM0045918

Synonyms (56)

Synonym
CHEMBL75782
6202-10-4
4,5-dihydroorotic acid
2,6-dioxohexahydropyrimidine-4-carboxylic acid
hydroorotic acid
5,6-dihydro-orotic acid
dl-dihydroortotic acid
CHEBI:30865 ,
dihydroorotic acid
155-54-4
dl-dihydroorotic acid
5,6-dihydroorotate
EBA89F91-9BA4-4F53-A555-AACB4A7DF0FA
2,6-dioxo-1,3-diazinane-4-carboxylic acid
AKOS006228089
(s)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
39lrk7ux5b ,
unii-39lrk7ux5b
4-pyrimidinecarboxylic acid, hexahydro-2,6-dioxo-
FT-0602259
FT-0627848
AM20100519
SCHEMBL121953
5,6-dihydrouracil-6-carboxylic acid
hydroorotic acid, (+/-)-
6-hydrouracilcarboxylic acid
5,6-dihydroorotic acid
hydroorotic acid, dl-
(+/-)-dihydroorotic acid
hydroorotic acid [mi]
dl-4,5-dihydroorotic acid
hydroorotic acid dl-form [mi]
d-hydrooroticacid
CS-0046700
(r)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
(+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(s)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(r)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
r,s-hydroorotate
2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
l-hydroorotate
FT-0747363
Q2823223
dl-hydroorotic acid
SY042036
2,6-dioxo-hexahydro-pyrimidine-4-carboxylicacid
AS-18439
BCP33011
2,6-dioxohexahydropyrimidine-4-carboxylicacid
D72863
SB56808
SB45071
DTXSID40861839
EN300-297330
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
secondary amideA derivative of two oxoacids RkE(=O)l(OH)m (l =/= 0) in which two acyl groups are attached to the amino or substituted amino group.
monocarboxylic acidAn oxoacid containing a single carboxy group.
pyrimidinemonocarboxylic acid
N-acylureaA member of the class of ureas that has the general formula R-CO-NH-CO-NH2 or R-CO-NH-CO-NH-CO-R', formally derived by the acylation of one or both of the nitrogens of a urea moiety.
[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]

Pathways (1)

PathwayProteinsCompounds
Biochemical pathways: part I0466

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CAD protein [Includes: Glutamine-dependent carbamoyl-phosphate synthase Mus musculus (house mouse)Km4.00004.00004.00004.0000AID55737
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID275418Inhibition of Plasmodium falciparum DHODH F188A mutant2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Design and synthesis of potent inhibitors of the malaria parasite dihydroorotate dehydrogenase.
AID275413Inhibition of recombinant Plasmodium falciparum DHODH2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Design and synthesis of potent inhibitors of the malaria parasite dihydroorotate dehydrogenase.
AID275417Inhibition of Plasmodium falciparum DHODH H185A mutant2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Design and synthesis of potent inhibitors of the malaria parasite dihydroorotate dehydrogenase.
AID275419Inhibition of Plasmodium falciparum DHODH R265K mutant2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Design and synthesis of potent inhibitors of the malaria parasite dihydroorotate dehydrogenase.
AID55737Compound was evaluated for the inhibition of dihydroorotase enzyme from mouse Ehrlich ascites at the concentration of 10 uM and at pH 7.371984Journal of medicinal chemistry, Feb, Volume: 27, Issue:2
Design and synthesis of tetrahedral intermediate analogues as potential dihydroorotase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (61)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (24.59)18.7374
1990's10 (16.39)18.2507
2000's21 (34.43)29.6817
2010's13 (21.31)24.3611
2020's2 (3.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.41

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.41 (24.57)
Research Supply Index4.13 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.64%)6.00%
Case Studies1 (1.64%)4.05%
Observational1 (1.64%)0.25%
Other58 (95.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]