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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:40 UTC
HMDB IDHMDB0000788
Secondary Accession Numbers
  • HMDB00788
Metabolite Identification
Common NameOrotidine
DescriptionOrotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a beta-N1-glycosidic bond. It is a water-soluble solid. Orotidine is found in bacteria, fungi, plants, and animals. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in the biosynthesis of pyrimidine nucleosides (cytidine and uridine) that are found in nucleic acids (as the nucleotides containing the bases cytosine and uracil). Orotidine itself is not a component of nucleic acid. Orotidine monophosphate (OMP) is converted to uridine monophosphate by OMP decarboxylase, which is inhibited by mononucleotide precursors. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine, which is one such inhibitor, indicating that the subject has increased DNA synthesis due to cancer. Orotidine was first isolated from a mutant strain of the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell (PMID: 14853953 ).
Structure
Data?1582752156
Synonyms
ValueSource
3-Ribofuranosylorotic acidChEBI
6-CarboxyuridineChEBI
3-RibofuranosylorotateGenerator
Orotic acid ribosideHMDB
Orotidine, ammonium saltHMDB
Chemical FormulaC10H12N2O8
Average Molecular Weight288.2109
Monoisotopic Molecular Weight288.05936537
IUPAC Name3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Traditional Nameorotidine
CAS Registry Number314-50-1
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O
InChI Identifier
InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1
InChI KeyFKCRAVPPBFWEJD-XVFCMESISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Hydropyrimidine carboxylic acid derivative
  • Pyrimidine-6-carboxylic acid
  • Pyrimidine-6-carboxylic acid or derivatives
  • Hydroxypyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 400 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility44.7 g/LALOGPS
logP-2ALOGPS
logP-2.8ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.87 m³·mol⁻¹ChemAxon
Polarizability25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.45531661259
DarkChem[M-H]-159.93731661259
AllCCS[M+H]+162.46532859911
AllCCS[M-H]-159.2632859911
DeepCCS[M+H]+162.9930932474
DeepCCS[M-H]-160.59530932474
DeepCCS[M-2H]-194.63230932474
DeepCCS[M+Na]+169.62730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OrotidineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O3713.4Standard polar33892256
OrotidineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O2247.4Standard non polar33892256
OrotidineOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O2863.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Orotidine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O2558.8Semi standard non polar33892256
Orotidine,1TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(C(=O)O)=CC(=O)[NH]C1=O2576.5Semi standard non polar33892256
Orotidine,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@@H]1O2583.9Semi standard non polar33892256
Orotidine,1TMS,isomer #4C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2556.0Semi standard non polar33892256
Orotidine,1TMS,isomer #5C[Si](C)(C)N1C(=O)C=C(C(=O)O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O2615.9Semi standard non polar33892256
Orotidine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O2532.3Semi standard non polar33892256
Orotidine,2TMS,isomer #10C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2604.7Semi standard non polar33892256
Orotidine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2558.3Semi standard non polar33892256
Orotidine,2TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2559.1Semi standard non polar33892256
Orotidine,2TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O2594.1Semi standard non polar33892256
Orotidine,2TMS,isomer #5C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@@H]1O[Si](C)(C)C2577.5Semi standard non polar33892256
Orotidine,2TMS,isomer #6C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C2545.9Semi standard non polar33892256
Orotidine,2TMS,isomer #7C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(C(=O)O)=CC(=O)N([Si](C)(C)C)C1=O2608.9Semi standard non polar33892256
Orotidine,2TMS,isomer #8C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O2577.8Semi standard non polar33892256
Orotidine,2TMS,isomer #9C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@@H]1O2613.8Semi standard non polar33892256
Orotidine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2528.6Semi standard non polar33892256
Orotidine,3TMS,isomer #10C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O2618.5Semi standard non polar33892256
Orotidine,3TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2532.8Semi standard non polar33892256
Orotidine,3TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O2582.0Semi standard non polar33892256
Orotidine,3TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2531.1Semi standard non polar33892256
Orotidine,3TMS,isomer #5C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2587.5Semi standard non polar33892256
Orotidine,3TMS,isomer #6C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2593.4Semi standard non polar33892256
Orotidine,3TMS,isomer #7C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2528.9Semi standard non polar33892256
Orotidine,3TMS,isomer #8C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@@H]1O[Si](C)(C)C2610.0Semi standard non polar33892256
Orotidine,3TMS,isomer #9C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C2604.0Semi standard non polar33892256
Orotidine,4TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2527.4Semi standard non polar33892256
Orotidine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2610.8Semi standard non polar33892256
Orotidine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2614.8Semi standard non polar33892256
Orotidine,4TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2600.8Semi standard non polar33892256
Orotidine,4TMS,isomer #5C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2622.6Semi standard non polar33892256
Orotidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2620.8Semi standard non polar33892256
Orotidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2778.9Standard non polar33892256
Orotidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C)=CC(=O)N([Si](C)(C)C)C2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2801.1Standard polar33892256
Orotidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O2806.3Semi standard non polar33892256
Orotidine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(C(=O)O)=CC(=O)[NH]C1=O2823.6Semi standard non polar33892256
Orotidine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@@H]1O2829.9Semi standard non polar33892256
Orotidine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2811.8Semi standard non polar33892256
Orotidine,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)C=C(C(=O)O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O2853.7Semi standard non polar33892256
Orotidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O3016.3Semi standard non polar33892256
Orotidine,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O3079.0Semi standard non polar33892256
Orotidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3027.2Semi standard non polar33892256
Orotidine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3012.5Semi standard non polar33892256
Orotidine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O3067.9Semi standard non polar33892256
Orotidine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3010.8Semi standard non polar33892256
Orotidine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3014.9Semi standard non polar33892256
Orotidine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C1=O3081.0Semi standard non polar33892256
Orotidine,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3019.4Semi standard non polar33892256
Orotidine,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@@H]1O3088.2Semi standard non polar33892256
Orotidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3254.9Semi standard non polar33892256
Orotidine,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3305.7Semi standard non polar33892256
Orotidine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)[NH]C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3237.4Semi standard non polar33892256
Orotidine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O3285.6Semi standard non polar33892256
Orotidine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3193.5Semi standard non polar33892256
Orotidine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3301.9Semi standard non polar33892256
Orotidine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3297.0Semi standard non polar33892256
Orotidine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3217.3Semi standard non polar33892256
Orotidine,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3307.3Semi standard non polar33892256
Orotidine,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3299.5Semi standard non polar33892256
Orotidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)[NH]C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3438.4Semi standard non polar33892256
Orotidine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3514.1Semi standard non polar33892256
Orotidine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3507.4Semi standard non polar33892256
Orotidine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3516.1Semi standard non polar33892256
Orotidine,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3521.1Semi standard non polar33892256
Orotidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3710.4Semi standard non polar33892256
Orotidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3615.4Standard non polar33892256
Orotidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3320.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i3-9230000000-e2c457e981d3f20213c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (4 TMS) - 70eV, Positivesplash10-03ei-4340390000-f308e272596bbf4876aa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Orotidine GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Orotidine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0f92-6790000000-22b02fcae382ac45192a2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 10V, Positive-QTOFsplash10-0a4r-0940000000-ae1aee48fbe832808af52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 20V, Positive-QTOFsplash10-0a4r-1920000000-8d5291c4fd7f7d30f0bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 40V, Positive-QTOFsplash10-0aou-8900000000-b3e3dadd94fb667cbb002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 10V, Negative-QTOFsplash10-052o-3970000000-a100d1c804d27c0b6e972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 20V, Negative-QTOFsplash10-0bt9-0910000000-1a9d30040efa9eecd74d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 40V, Negative-QTOFsplash10-01ox-9600000000-001a262ee2894d294d1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 10V, Positive-QTOFsplash10-000i-0910000000-db12fcd4210da39a93712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 20V, Positive-QTOFsplash10-06ri-0910000000-cb586e3766ceeef714942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 40V, Positive-QTOFsplash10-000i-3900000000-7e74435ea88ec8add7cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 10V, Negative-QTOFsplash10-000i-0190000000-5c6d124476de69b9c5892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 20V, Negative-QTOFsplash10-08fr-1940000000-64fcb770cc2756bd03482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Orotidine 40V, Negative-QTOFsplash10-0006-9600000000-6b704e1f9de9d9c4d8f62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.167 +/- 5.556 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified149.0 +/- 13.0 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.12 +/- 0.20 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified<0.47 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified70.139 +/- 46.875 uMAdult (>18 years old)Both
Uremia
details
UrineDetected and Quantified0.52 umol/mmol creatinineAdult (>18 years old)Female
Orotic aciduria I
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Orotic aciduria I
  1. Grohmann K, Lauffer H, Lauenstein P, Hoffmann GF, Seidlitz G: Hereditary orotic aciduria with epilepsy and without megaloblastic anemia. Neuropediatrics. 2015 Apr;46(2):123-5. doi: 10.1055/s-0035-1547341. Epub 2015 Mar 10. [PubMed:25757096 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012085
KNApSAcK IDC00054976
Chemspider ID83729
KEGG Compound IDC01103
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOrotidine
METLIN ID5754
PubChem Compound92751
PDB IDNot Available
ChEBI ID25722
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000252
Good Scents IDNot Available
References
Synthesis ReferenceCurra, William V.; Angle, Robert B. Synthesis of orotidine. Tetrahedron Letters (1963), (8), 533-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Arranz JA, Riudor E, Rodes M, Roig M, Climent C, Rubio V, Sentis M, Burlina A: Optimization of allopurinol challenge: sample purification, protein intake control, and the use of orotidine response as a discriminative variable improve performance of the test for diagnosing ornithine carbamoyltransferase deficiency. Clin Chem. 1999 Jul;45(7):995-1001. [PubMed:10388475 ]
  2. Harris ML, Oberholzer VG: Conditions affecting the colorimetry of orotic acid and orotidine in urine. Clin Chem. 1980 Mar;26(3):473-9. [PubMed:7363468 ]
  3. van Kuilenburg AB, van Lenthe H, Loffler M, van Gennip AH: Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clin Chem. 2004 Nov;50(11):2117-24. Epub 2004 Sep 16. [PubMed:15375016 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  5. MICHELSON AM, DRELL W, MITCHELL HK: A new ribose nucleoside from Neurospora; "orotidine". Proc Natl Acad Sci U S A. 1951 Jul;37(7):396-9. doi: 10.1073/pnas.37.7.396. [PubMed:14853953 ]