ChemFOnt: Showing chemical card for Orotidylic acid (CFc000000144)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:27 UTC

Chemfont ID

CFc000000144

Molecule Identification

Common Name

Orotidylic acid

Definition

847

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Orotidylate	Generator

Chemical Formula

C₁₀H₁₃N₂O₁₁P

Average Molecular Weight

368.1908

Monoisotopic Molecular Weight

368.02569578

IUPAC Name

3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid

Traditional Name

3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-6-hydroxy-2-oxopyrimidine-4-carboxylic acid

CAS Registry Number

2149-82-8

SMILES

OC1C(COP(O)(O)=O)OC(C1O)N1C(=O)N=C(O)C=C1C(O)=O

InChI Identifier

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)

InChI Key

KYOBSHFOBAOFBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Pyrimidine ribonucleoside monophosphate
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Pyrimidine-6-carboxylic acid or derivatives
Pyrimidine-6-carboxylic acid
Hydropyrimidine carboxylic acid derivative
Monoalkyl phosphate
Pyrimidone
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Phosphoric acid ester
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Urea
Lactam
1,2-diol
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Prostate (HMDB: HMDB0000218)

Non-excretory biofluid

Biofluid or Excreta

Prostate Tissue (PMID: 19212411)

Cellular substructure

Cytoplasm (HMDB: HMDB0000218)

Source

Exogenous

Exogenous (HMDB: HMDB0000218)

Endogenous

Endogenous (HMDB: HMDB0000218)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyrimidine Metabolism (PathBank: SMP0087340)
Glycine and Serine Metabolism (PathBank: SMP0087466)
Pyrimidine Metabolism (PathBank: SMP0002370)

Disease pathway

Sarcosinemia (PathBank: SMP0120521)
Beta-Ureidopropionase Deficiency (PathBank: SMP0120678)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0120694)
UMP Synthase Deficiency (Orotic Aciduria) (PathBank: SMP0120507)
Non-Ketotic Hyperglycinemia (PathBank: SMP0120534)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0120872)
Dihydropyrimidinase Deficiency (PathBank: SMP0120473)
Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0120695)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0120770)
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) (PathBank: SMP0120530)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.39 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	206.65 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.07 m³·mol⁻¹	ChemAxon
Polarizability	29.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012321

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orotidine 5'-monophosphate

METLIN ID

Not Available

PubChem Compound

968

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ueda, Tohru; Yamamoto, Miyako; Yamane, Akira; Imazawa, Masaoki; Inoue, Hideo. Nucleosides and nucleotides. XXIII. Conversion of uridine nucleotides to the 6-cyano derivatives: synthesis of orotidylic acid. Journal of Carbohydrates, Nucleosides, Nucleotides (1978), 5(3), 261-71.

Showing chemical card for Orotidylic acid (CFc000000144)

MOL for CFc000000144 (Orotidylic acid)

3D MOL for CFc000000144 (Orotidylic acid)

3D SDF for CFc000000144 (Orotidylic acid)

3D-SDF for CFc000000144 (Orotidylic acid)

PDB for CFc000000144 (Orotidylic acid)

3D PDB for CFc000000144 (Orotidylic acid)

SMILES for CFc000000144 (Orotidylic acid)

INCHI for CFc000000144 (Orotidylic acid)

Structure for CFc000000144 (Orotidylic acid)

3D Structure for CFc000000144 (Orotidylic acid)