Showing Compound Orotidine (FDB012085)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:59 UTC

Update date

2019-11-26 03:06:09 UTC

Primary ID

FDB012085

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Orotidine

Description

Isolated from Phaseolus vulgaris (kidney bean) Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a β-N1-glycosidic bond. It is found in bacteria, fungi and plants. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids. Ornitidine itself is not a component of nucleic acid. Large amounts of ornitidine are excreted in the urine of cancer patients treated with 6-azauridine. ; Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a ?-N1-glycosidic bond. It is found in bacteria, fungi and plants. It was first isolated in 1951 from the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids. Orotidine itself is not a component of nucleic acid. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine.

CAS Number

314-50-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
1,2,3,6-Tetrahydro-2,6-dioxo-3-b-D-ribofuranosyl-4-pyrimidinecarboxylic acid, 9CI	db_source
3-b-D-Ribofuranosylorotic acid, 8CI	db_source
3-Ribofuranosylorotate	Generator
3-Ribofuranosylorotic acid	biospider
6-Carboxyuridine	biospider
6-Carboxyuridine, 8CI	db_source
Orotic acid riboside	biospider

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	33.5 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.4	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.19 m³·mol⁻¹	ChemAxon
Polarizability	24.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12N2O8

IUPAC name

3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid

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)

InChI Key

FKCRAVPPBFWEJD-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(C(O)C1O)N1C(=O)N=C(O)C=C1C(O)=O

Average Molecular Weight

288.2109

Monoisotopic Molecular Weight

288.05936537

Classification

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Not Available

Direct Parent

Pyrimidine 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
Pyrimidone
Hydropyrimidine
Monosaccharide
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Lactam
Urea
Secondary alcohol
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 41.67%; H 4.20%; N 9.72%; O 44.41%	DFC
Melting Point	Mp 200° (turns brown near)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Orotidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0abc-9230000000-293a68d8c2ffe4216aae	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0940000000-e4438f142f6ff2ba8677	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1920000000-94d096285cb9e65784d9	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-8900000000-d16857abd2338f86c216	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0k96-2950000000-cbc2612dbaeb4d2d8fff	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-0910000000-0c8b41b3e1f2ab273ab2	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9700000000-533485004aac59a5e1c2	2018-04-06	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

83729

ChEMBL ID

Not Available

KEGG Compound ID

C01103

Pubchem Compound ID

92751

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00788

CRC / DFC (Dictionary of Food Compounds) ID

HCZ97-N:HCZ97-N

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Orotidine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Orotidine (FDB012085)

Structure for FDB012085 (Orotidine)