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Details

Stereochemistry ACHIRAL
Molecular Formula 2C5H3N2O4.Zn
Molecular Weight 375.586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZINC OROTATE

SMILES

[Zn++].[O-]C(=O)C1=CC(=O)NC(=O)N1.[O-]C(=O)C2=CC(=O)NC(=O)N2

InChI

InChIKey=YNMDOZLVAPMCBD-UHFFFAOYSA-L
InChI=1S/2C5H4N2O4.Zn/c2*8-3-1-2(4(9)10)6-5(11)7-3;/h2*1H,(H,9,10)(H2,6,7,8,11);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H3N2O4
Molecular Weight 155.0883
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Orotic acid is a minor dietary constituent. Historically it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin and is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyl transferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Orotic acid levels are elevated in the urea cycle defects ornithine transcarbamylase (OTC) deficiency, citrullinemia and argininosuccinic acidemia, as well as the mitochondrial transport disorder hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome. Orotic acid is also elevated in hereditary orotic aciduria, or uridine monophosphate synthase deficiency, an autosomal recessive disorder characterized by megaloblastic anemia and crystalluria. In addition, orotic acid in combination with leflunomide is in the phase II of clinical trial to evaluate the clinical efficacy and safety of a combination in kidney transplant patients with high levels of Polyoma BK viruria for the purpose of preventing polyoma BK viremia and nephropathy, that could lead to kidney transplant loss from viral damage, acute rejection or both.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11172|||Q9UG49
Gene ID: 7372.0
Gene Symbol: UMPS
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Pyrimidine nucleobase ligands of orotate phosphoribosyltransferase from Toxoplasma gondii.
1999 Nov 1
Insight into the chemistry of flavin reduction and oxidation in Escherichia coli dihydroorotate dehydrogenase obtained by rapid reaction studies.
2001 Apr 10
A nonradioactive high-performance liquid chromatographic microassay for uridine 5'-monophosphate synthase, orotate phosphoribosyltransferase, and orotidine 5'-monophosphate decarboxylase.
2001 Dec 15
Theoretical studies of mechanisms and kinetic isotope effects on the decarboxylation of orotic acid and derivatives.
2001 Dec 5
[Passive orthostatic test in evaluation of efficiency of medical rehabilitation of flying personnel].
2001 Jan
Laboratory evaluation of urea cycle disorders.
2001 Jan
Simple gas chromatographic-mass spectrometric procedure for diagnosing pyrimidine degradation defects for prevention of severe anticancer side effects.
2001 Jul 5
Regulation of Cyp1a1 induction by dioxin as a function of cell cycle phase.
2001 Nov
[Orotic acid as a metabolic agent].
2002
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism.
2002 Dec 30
Diagnostic value of urinary orotic acid levels: applicable separation methods.
2002 Dec 5
Behavior of alginate gel beads containing chitosan salt prepared with water-soluble vitamins.
2002 Mar
Mapping the active site-ligand interactions of orotidine 5'-monophosphate decarboxylase by crystallography.
2002 Mar 26
The dimeric dihydroorotate dehydrogenase A from Lactococcus lactis dissociates reversibly into inactive monomers.
2002 Nov
Malarial dihydroorotate dehydrogenase. Substrate and inhibitor specificity.
2002 Nov 1
Equilibrium of formation of the 6-carbanion of UMP, a potential intermediate in the action of OMP decarboxylase.
2002 Nov 27
An investigation of orotic acid levels in the breastmilk of smoking and non-smoking mothers.
2002 Oct
Allopurinol challenge tests performed before and after living-related donor liver transplantation in citrullinaemia.
2003
[Mechanism of action of a novel antitumor preparation of chlofiden. Effect on RNA synthesis].
2003 Jan-Feb
Concentration and purification of orotic acid directly from whey with an expanded bed adsorption system.
2003 Jul 18
Magnesium-orotate supplementation for idiopathic infertile male patients: a randomized, placebo-controlled clinical pilot study.
2003 Jun
Crystallization and preliminary X-ray crystallographic analysis of orotate phosphoribosyltransferase from Helicobacter pylori.
2003 Jun 30
Involvement of voltage- and ligand-gated Ca2+ channels in the neuroexcitatory and synergistic effects of putative uremic neurotoxins.
2003 May
pdf1, a palmitoyl protein thioesterase 1 Ortholog in Schizosaccharomyces pombe: a yeast model of infantile Batten disease.
2004 Apr
Modest catalysis of the decarboxylation of orotate by hydrogen bonding: a theoretical model for orotidine- 5' -monophosphate decarboxylase.
2004 Apr
Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography.
2004 Jan-Feb
Thermodynamic basis of electron transfer in dihydroorotate dehydrogenase B from Lactococcus lactis: analysis by potentiometry, EPR spectroscopy, and ENDOR spectroscopy.
2004 Jun 1
Patents

Sample Use Guides

Daily dose of leflunomide adjusted to target steady state blood levels of 50 ug/mL to 100 ug/mL of the active metabolite plus 600 mg orotic acid
Route of Administration: Oral
In Vitro Use Guide
By means of electron microscopic and quantitative methods at the explantate cultures of the fetal hippocampus in vitro the influence of the orotic acid, sodium orotate and methylglucamine orotate on the neurogenesis was investigated. After three days of the in vitro cultivation the neuroblasts influenced by these drugs show a smaller respectively not different degree of differentiation compared to the controls. Under the influence of the orotic acid and of its derivatives the neurogenesis is significantly stimulated. The drugs produce a significant increase of the membrane-bound ribosomes and polysomes. The total number of ribosomes increases following the application of orotic acid by 20%, of sodium-orotate by 48% and of methylglucamine-orotate by 23% compared to the controls (alpha = 0,1%). Sodium-orotate shows with reference to the neuronal development the clearest stimulatory effect. After 20 days in vitro the total number of ribosomes is by 60% higher at the treated cultures than in the controls. The results might suggest, that an enlarged supply of the pyrimidine nucleotide via a raising of the RNA- and the protein synthesis might stimulate the development of the neuroblasts even under the in vitro conditions.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:18 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:18 GMT 2023
Record UNII
Z722242H10
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZINC OROTATE
WHO-DD  
Common Name English
4-PYRIMIDINECARBOXYLIC ACID, 1,2,3,6-TETRAHYDRO-2,6-DIOXO-, ZINC SALT (2:1)
Systematic Name English
ZINC DIOROTATE
Common Name English
Zinc orotate [WHO-DD]
Common Name English
4-PYRIMIDINECARBOXYLIC ACID, 1,2,3,6-TETRAHYDRO-2,6-DIOXO-, ZINC COMPLEX
Common Name English
OROTATE ZINC
Common Name English
ZINC, BIS(1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLATO-.KAPPA.N3,.KAPPA.O4)-, (T-4)-
Common Name English
Code System Code Type Description
CAS
60388-02-5
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
PUBCHEM
108934
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
CAS
68399-76-8
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
ALTERNATIVE
RXCUI
11422
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8071481
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
269-988-0
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
262-207-4
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
FDA UNII
Z722242H10
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
SMS_ID
100000089533
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
EVMPD
SUB15759MIG
Created by admin on Fri Dec 15 15:50:18 GMT 2023 , Edited by admin on Fri Dec 15 15:50:18 GMT 2023
PRIMARY
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SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY