NAV

Orotidylic acid

Identification

Generic Name
Orotidylic acid
DrugBank Accession Number
DB02957
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 368.1908
Monoisotopic: 368.02569578
Chemical Formula
C10H13N2O11P
Synonyms
  • 5-(Dihydrogen phosphate)orotidine
  • 6-carboxy-5'-uridylic acid
  • orotidine 5'-(dihydrogen phosphate)
  • Orotidine 5'-monophosphate
  • Orotidine 5'-phosphate
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Glycine and Serine MetabolismMetabolic
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
beta-Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Non-Ketotic HyperglycinemiaDisease
SarcosinemiaDisease
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Hyperglycinemia, Non-KetoticDisease
3-Phosphoglycerate Dehydrogenase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Hydropyrimidine carboxylic acids and derivatives / Pyrimidinecarboxylic acids / Monoalkyl phosphates / Pyrimidones / Tetrahydrofurans / Heteroaromatic compounds / Vinylogous amides
show 12 more
Substituents
1,2-diol / Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine ribonucleoside 5'-monophosphate (CHEBI:15842)
Affected organisms
Not Available

Chemical Identifiers

UNII
H0ARN8U4Y9
CAS number
2149-82-8
InChI Key
KYOBSHFOBAOFBF-XVFCMESISA-N
InChI
InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1
IUPAC Name
3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0000218
KEGG Compound
C01103
PubChem Compound
160617
PubChem Substance
46507709
ChemSpider
141140
BindingDB
21336
ChEBI
15842
ChEMBL
CHEMBL1207358
ZINC
ZINC000004095542
PDBe Ligand
OMP
Wikipedia
Orotidine_5%27-monophosphate
PDB Entries
1km6 / 1sto / 2prz / 2qcl / 2wns / 2za1 / 6yvk / 6yvl / 6yvm / 6yvn …
show 8 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.61 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.9Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.21Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area203.16 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity70.74 m3·mol-1Chemaxon
Polarizability29.65 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9705
Blood Brain Barrier+0.7209
Caco-2 permeable-0.8256
P-glycoprotein substrateNon-substrate0.7908
P-glycoprotein inhibitor INon-inhibitor0.8992
P-glycoprotein inhibitor IINon-inhibitor0.9847
Renal organic cation transporterNon-inhibitor0.9516
CYP450 2C9 substrateNon-substrate0.6826
CYP450 2D6 substrateNon-substrate0.8565
CYP450 3A4 substrateNon-substrate0.5833
CYP450 1A2 substrateNon-inhibitor0.896
CYP450 2C9 inhibitorNon-inhibitor0.9033
CYP450 2D6 inhibitorNon-inhibitor0.8962
CYP450 2C19 inhibitorNon-inhibitor0.8726
CYP450 3A4 inhibitorNon-inhibitor0.8657
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9457
Ames testNon AMES toxic0.9017
CarcinogenicityNon-carcinogens0.9148
BiodegradationReady biodegradable0.6981
Rat acute toxicity2.1330 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9787
hERG inhibition (predictor II)Non-inhibitor0.8231
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9512000000-a3f8062edabfeda1eaa8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-1159000000-6a774661e76513533ca8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0951000000-3529db30a9d0f0e0a457
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-6029000000-fa78a68ed099be66bfbc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05n0-0940000000-3ed76c6a5b0e0aca1bf3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9012000000-1127536505e046587ecc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9311000000-dec74fde5bdd4f43e88b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.7931497
predicted
DarkChem Lite v0.1.0
[M-H]-188.2349497
predicted
DarkChem Lite v0.1.0
[M-H]-170.20602
predicted
DeepCCS 1.0 (2019)
[M+H]+190.8119497
predicted
DarkChem Lite v0.1.0
[M+H]+190.8539497
predicted
DarkChem Lite v0.1.0
[M+H]+172.60158
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.6223497
predicted
DarkChem Lite v0.1.0
[M+Na]+188.5489497
predicted
DarkChem Lite v0.1.0
[M+Na]+178.54315
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52