|
call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__59027224646899__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__59027224646899__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16742","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__59027224646899__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"59027224646899","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__59027224646899__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 07031313463D starting HoverWatcher_5 Time for openFile( Marvin 07031313463D 15 15 0 0 0 0 999 V2000 -0.2827 -0.5449 -0.0534 C 0 0 0 0 0 0 0 0 0 4 0 0 1.0456 -0.5228 -0.0690 N 0 0 0 0 0 0 0 0 0 3 0 0 -0.9447 0.6411 -0.0411 C 0 0 0 0 0 0 0 0 0 5 0 0 -0.2094 1.7975 -0.0233 C 0 0 0 0 0 0 0 0 0 6 0 0 1.7404 0.5932 -0.0353 C 0 0 0 0 0 0 0 0 0 2 0 0 1.1020 1.7382 0.0223 N 0 0 0 0 0 0 0 0 0 1 0 0 -0.9227 -1.7456 -0.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0515 -1.8797 0.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4055 -2.7628 -0.4826 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7483 2.8939 -0.0531 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9606 0.5676 -0.0612 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5136 -1.3331 -0.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5920 2.5316 0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9390 0.6899 -0.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4504 -2.6640 0.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 2 1 0 0 0 0 2 12 1 0 0 0 0 1 3 2 0 0 0 0 3 4 1 0 0 0 0 4 10 2 0 0 0 0 2 5 1 0 0 0 0 5 11 2 0 0 0 0 5 6 1 0 0 0 0 4 6 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 3 14 1 0 0 0 0 8 15 1 0 0 0 0 M END): 16 ms reading 15 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 15 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
|
Orotic acid () is a pyrimidinedione and a carboxylic acid. 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.
The compound is synthesized in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate.
|
Read full article at Wikipedia
|
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11) |
PXQPEWDEAKTCGB-UHFFFAOYSA-N |
OC(=O)c1cc(=O)[nH]c(=O)[nH]1 |
|
Mus musculus
(NCBI:txid10090)
|
Source: BioModels - MODEL1507180067
See:
PubMed
|
Escherichia coli
(NCBI:txid562)
|
See:
PubMed
|
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
|
|
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
|
|
View more via ChEBI Ontology
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
|
Orotic acid
|
KEGG COMPOUND
|
OROTIC ACID
|
PDBeChem
|
Orotsäure
|
ChEBI
|
Uracil-6-carboxylic acid
|
KEGG COMPOUND
|
3402
|
DrugCentral
|
C00019689
|
KNApSAcK
|
C00295
|
KEGG COMPOUND
|
D00055
|
KEGG DRUG
|
DB02262
|
DrugBank
|
HMDB0000226
|
HMDB
|
ORO
|
PDBeChem
|
OROTATE
|
MetaCyc
|
Orotic_acid
|
Wikipedia
|
View more database links |
101990
|
Gmelin Registry Number
|
Gmelin
|
383901
|
Reaxys Registry Number
|
Reaxys
|
65-86-1
|
CAS Registry Number
|
KEGG COMPOUND
|
65-86-1
|
CAS Registry Number
|
ChemIDplus
|
65-86-1
|
CAS Registry Number
|
NIST Chemistry WebBook
|
Khajehsharifi H, Tavallali H, Shekoohi M, Sadeghi M (2013) Spectrophotometric simultaneous determination of orotic acid, creatinine and uric acid by orthogonal signal correction-partial least squares in spiked real samples. Drug testing and analysis 5, 353-360 [PubMed:22371390] [show Abstract] An orthogonal signal correction-partial least squares (OSC-PLS) method was developed for the simultaneous spectrophotometric determination of orotic acid (OA), creatinine (CRE), and uric acid (UA) in spiked real samples. By multivariate calibration methods, such as PLS regression, it is possible to obtain a model adjusted to the concentration values of the mixtures used in the calibration range. The effect of OSC used to remove the information unrelated to the target variables is studied. In this study, the calibration model is based on absorption spectra in the 220-320 nm rang for 36 different mixtures of OA, CRE and UA. Calibration matrices contained 1.74-47.00 of OA, 1.13-33.95 of CRE, and 1.68-28.58 of UA in µg/ml. The number of principal component for OA, CRE, and UA with OSC were 3, 4, and 4, and 4, 6, and 5, without OSC, respectively. The evaluation of the prediction errors for the prediction set reveals that the OSC-treated data give substantially lower root mean square error of prediction (RMSEP) values than the original data. The RMSEP for OA, CRE, and UA with OSC were 0.69, 0.20, and 0.53 and 0.80, 0.69, and 0.73 without OSC, respectively. The proposed method was applied for the simultaneous determination of OA, CRE, and UA in spiked biological fluids with satisfactory results. | Gerhardt V, Tutughamiarso M, Bolte M (2012) Conformational studies of hydantoin-5-acetic acid and orotic acid. Acta crystallographica. Section C, Crystal structure communications 68, o92-8 [PubMed:22307261] [show Abstract] Hydantoin-5-acetic acid [2-(2,5-dioxoimidazolidin-4-yl)acetic acid] and orotic acid (2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid) each contain one rigid acceptor-donor-acceptor hydrogen-bonding site and a flexible side chain, which can adopt different conformations. Since both compounds may be used as coformers for supramolecular complexes, they have been crystallized in order to examine their conformational preferences, giving solvent-free hydantoin-5-acetic acid, C(5)H(6)N(2)O(4), (I), and three crystals containing orotic acid, namely, orotic acid dimethyl sulfoxide monosolvate, C(5)H(4)N(2)O(4)·C(2)H(6)OS, (IIa), dimethylammonium orotate-orotic acid (1/1), C(2)H(8)N(+)·C(5)H(3)N(2)O(4)(-)·C(5)H(4)N(2)O(4), (IIb), and dimethylammonium orotate-orotic acid (3/1), 3C(2)H(8)N(+)·3C(5)H(3)N(2)O(4)(-)·C(5)H(4)N(2)O(4), (IIc). The crystal structure of (I) shows a three-dimensional network, with the acid function located perpendicular to the ring. Interestingly, the hydroxy O atom acts as an acceptor, even though the carbonyl O atom is not involved in any hydrogen bonds. However, in (IIa), (IIb) and (IIc), the acid functions are only slightly twisted out of the ring planes. All H atoms of the acidic functions are directed away from the rings and, with respect to the carbonyl O atoms, they show an antiperiplanar conformation in (I) and synperiplanar conformations in (IIa), (IIb) and (IIc). Furthermore, in (IIa), (IIb) and (IIc), different conformations of the acid O=C-C-N torsion angle are observed, leading to different hydrogen-bonding arrangements depending on their conformation and composition. | Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012) Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical chemistry 84, 6429-6437 [PubMed:22770225] [show Abstract] Metabolic profiles of biofluids obtained by atmospheric pressure ionization mass spectrometry-based technologies contain hundreds to thousands of features, most of them remaining unknown or at least not characterized in analytical systems. We report here on the annotation of the human adult urinary metabolome and metabolite identification from electrospray ionization mass spectrometry (ESI-MS)-based metabolomics data sets. Features of biological interest were first of all annotated using the ESI-MS database of the laboratory. They were also grouped, thanks to software tools, and annotated using public databases. Metabolite identification was achieved using two complementary approaches: (i) formal identification by matching chromatographic retention times, mass spectra, and also product ion spectra (if required) of metabolites to be characterized in biological data sets to those of reference compounds and (ii) putative identification from biological data thanks to MS/MS experiments for metabolites not available in our chemical library. By these means, 384 metabolites corresponding to 1484 annotated features (659 in negative ion mode and 825 in positive ion mode) were characterized in human urine samples. Of these metabolites, 192 and 66 were formally and putatively identified, respectively, and 54 are reported in human urine for the first time. These lists of features could be used by other laboratories to annotate their ESI-MS metabolomics data sets. | Niu H, Chen Y, Xie J, Chen X, Bai J, Wu J, Liu D, Ying H (2012) Ion-exclusion chromatography determination of organic acid in uridine 5'-monophosphate fermentation broth. Journal of chromatographic science 50, 709-713 [PubMed:22634191] [show Abstract] Simultaneous determination of organic acids using ion-exclusion liquid chromatography and ultraviolet detection is described. The chromatographic conditions are optimized when an Aminex HPX-87H column (300 × 7.8 mm) is employed, with a solution of 3 mmol/L sulfuric acid as eluent, a flow rate of 0.4 mL/min and a column temperature of 60°C. Eight organic acids (including orotic acid, α-ketoglutaric acid, citric acid, pyruvic acid, malic acid, succinic acid, lactic acid and acetic acid) and one nucleotide are successfully quantified. The calibration curves for these analytes are linear, with correlation coefficients exceeding 0.999. The average recovery of organic acids is in the range of 97.6% ∼ 103.1%, and the relative standard deviation is in the range of 0.037% ∼ 0.38%. The method is subsequently applied to obtain organic acid profiles of uridine 5'-monophosphate culture broth fermented from orotic acid by Saccharomyces cerevisiae. These data demonstrate the quantitative accuracy for nucleotide fermentation mixtures, and suggest that the method may also be applicable to other biological samples. | D'Apolito O, Garofalo D, la Marca G, Dello Russo A, Corso G (2012) Reference intervals for orotic acid in urine, plasma and dried blood spot using hydrophilic interaction liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 883-884, 155-160 [PubMed:22019295] [show Abstract] Orotic acid (OA), a marker of hereditary orotic aciduria, is usually used for the differential diagnosis of some hyperammonemic inherited defects of urea cycle and of basic amino acid transporters. This study was aimed to establish age related reference intervals of OA in urine, and for the first time in plasma, and dried blood spot (DBS) from 229 apparently healthy subjects aged from three days to 40 years. The quantification of OA was performed by a previously implemented method, using a stable isotope dilution with 1,3-[(15)N(2)]-orotic acid and hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS). The method has proved to be sensitive and accurate for a quantitative analysis of OA also in DBS and plasma. According to previous studies, urinary OA levels (mmol/mol of creatinine) decrease significantly with age. The upper limits (as 99th %ile) were of 3.44 and 1.30 in groups aged from three days to 1 year (group 1) and from 1 year to 12 years (group 2), respectively; in teenagers (from 13 to 19 years; group 3) and adults (from 20 to 40 years; group 4) urinary levels became more stable and the upper limits were of 0.64 and 1.21, respectively. Furthermore, OA levels in DBS (μM) also resulted significantly higher in subjects of group 1 (upper limit of 0.89) than in subjects of groups 2, 3 and 4 (upper limits of 0.24, 0.21, and 0.29, respectively). OA levels in plasma (μM) were significantly lower in subjects of group 3 (upper limit of 0.30) than in subjects of groups 1, 2, and 4 (upper limits of 0.59, 0.48, and 0.77, respectively). This method was also employed for OA quantification in plasma and DBS of 17 newborns affected by urea cycle defects, resulting sensitive and specific enough to screen these disorders. | Fryčák P, Jirkovský J, Ranc V, Bednář P, Havlíček V, Lemr K (2012) Secondary processes in atmospheric pressure chemical ionization-ion trap mass spectrometry: a case study of orotic acid. Journal of mass spectrometry : JMS 47, 720-726 [PubMed:22707164] [show Abstract] Atmospheric pressure chemical ionization is known for producing unusual artifacts of the ionization process in some cases. In this work, processes occuring in atmospheric pressure chemical ionization/MS of orotic acid that afforded ions accompanying protonated and deprotonated orotic acid molecules in the spectra were studied. Two processes ran in parallel in the ion source: decarboxylation of neutral orotic acid and collision-induced dissociation of its protonated or deprotonated form. A procedure discerning pre-ionization decomposition and post-ionization dissociation by manipulating ion source parameters was proposed. Experiments with isotopically labeled solvents confirmed ion-molecule reactions of the product of collision-induced dissociation of protonated orotic acid with solvent molecules in the ion source and even under vacuum in the ion trap. | Pôrto LC, de Castro CH, Savergnini SS, Santos SH, Ferreira AV, Cordeiro LM, Sobrinho DB, Santos RA, de Almeida AP, Botion LM (2012) Improvement of the energy supply and contractile function in normal and ischemic rat hearts by dietary orotic acid. Life sciences 90, 476-483 [PubMed:22285839] [show Abstract]
AimsAs cardiac performance is closely related to its energy supply, our study investigated the effect of the orotic acid cardioprotective agent on the pathways of energy supply, in both conditions of normal flow and ischemia.Main methodsMale Wistar rats were fed during nine days with a balanced diet only or supplemented with 1% orotic acid.Key findingsDietary administration of orotic acid increased the cardiac utilization of fatty acids, activity of the lipoprotein lipase, expression of the gene of peroxisome proliferator-activated receptor α and its target enzymes. In addition, orotic acid increased the myocardial uptake and incorporation of glucose, glycogen content and level of GLUT4, concentration of glycolytic metabolites and lactate production in both experimental conditions, baseline and after regional ischemia.SignificanceThus, in orotic acid hearts there was a simultaneous stimulus of fatty acid oxidation and glycolytic pathway, reflected in increased energetic content even in pre-ischemia. The analysis of the cardiac contractility index showed a positive inotropic effect of orotic acid due, at least in part, to the increased availability of energy. The result allows us to suggest that the metabolic changes induced by orotic acid result in appreciable alterations on myocardial contractile function. | Jung EJ, Lee KY, Lee BH (2012) Proliferating effect of orotic acid through mTORC1 activation mediated by negative regulation of AMPK in SK-Hep1 hepatocellular carcinoma cells. The Journal of toxicological sciences 37, 813-821 [PubMed:22863860] [show Abstract] Orotic acid (OA) is a tumor promoter of experimental liver carcinogenesis initiated by DNA reactive carcinogens, the molecular mechanisms of which have not been fully elucidated. OA increases cell proliferation and decreases apoptosis in serum-starved SK-Hep1 hepatocellular carcinoma cells, which may ascribe to the inhibition of AMP-activated protein kinase (AMPK) phosphorylation and thus activation of mammalian target of rapamycin complex 1 (mTORC1). The effects of OA on mTORC1 activation, cell proliferation, and cell-cycle progression to S and G2/M phases were completely reversed by rapamycin. Activation of AMPK by a constitutively active mutant or aminoimidazole carboxamide ribonucleotide (AICAR) rescued the effects of OA. In conclusion, OA increases the proliferation and decreases the starvation-induced apoptosis of SK-Hep1 cells via mTORC1 activation mediated by negative regulation of AMPK. | Asai M, Sumi S, Kidouchi K, Imaeda H, Togari H, Wada Y (2000) Urinary pyrimidine analysis in healthy newborns, infants, children, adults and patients with congenital metabolic diseases. Pediatrics international : official journal of the Japan Pediatric Society 42, 499-503 [PubMed:11059538] [show Abstract]
BackgroundIn previous reports, the reference range for urinary pyrimidine was determined on the basis of a small number of samples, with data for only a few patients being reported. In the present study, we measured urinary pyrimidine compounds in 25 healthy newborns, 33 healthy infants, 130 healthy children and 166 healthy adults. In addition, we also analyzed urinary pyrimidine compounds in various patients with abnormal pyrimidine metabolism, such as congenital pyrimidine metabolism disorders and urea cycle disorders.MethodsWe analyzed urines by high-performance liquid chromatography with column switching. Analyses were performed with both a reverse-phase column and an anion-exchange column. The columns were connected by a column switch, with all systems being controlled automatically by a computerized system controller.ResultsThe excretion of pyrimidine compounds in patients with abnormal pyrimidine metabolism (containing heterozygotes) was out of our reference ranges.ConclusionsThese results suggest that urinary pyrimidine analysis is a useful index for the diagnosis of pyrimidine metabolism disorders, urea cycle disorders and these heterozygotes. Based on this large-group analysis of healthy individuals, we were able to determine the reference ranges of urinary orotic acid, dihydrouracil and uracil for each age group. | Gargallo J, Zimmerman D (1981) Effect of casein and starch infusion in the large intestine on nitrogen metabolism of growing swine. The Journal of nutrition 111, 1390-1396 [PubMed:7264771] [show Abstract] Eight crossbred female pigs (40 kg) with cannulae placed in the terminal ileum were used to evaluate the effect of infusions of casein starch and casein plus starch on organic matter fermentation and microbial protein synthesis in the large intestine, and their effect on urinary urea and orotic acid excretion, and on nitrogen (N) retention. Infused casein and starch were both totally digested. Nitrogen retention was increased (P greater than 0.05) when casein was infused. Starch infusion resulted in an increase (P greater than 0.05) in fecal N in the form of total protein (amino acids). The high correlation (P greater than 0.01) between fecal total protein and RNA indicates that the increase in fecal N resulted from an increase in microbial protein synthesis. About 5.2 g of bacterial protein was synthesized per 100 g of cornstarch fermented in the large intestine. Casein infusion increase (P greater than 0.05) total urinary N. Differences between treatments for urinary N were entirely because of changes in urinary urea. Urinary ammonia and unaccounted N were not affected by treatments. Urinary orotic acid was a good indicator of the urea cycle activity because of its hig correlation (P greater than 0.0) with urinary urea. Plasma urea N concentration was increased (P greater than 0.05) only when casein plus starch was infused. |
|