ChemFOnt: Showing chemical card for 4,5-Dihydroorotic acid (CFc000000406)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:47 UTC

Chemfont ID

CFc000000406

Molecule Identification

Common Name

4,5-Dihydroorotic acid

Definition

4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076 ). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,6-Dihydro-orotic acid	ChEBI
DL-Dihydroortotic acid	ChEBI
Hydroorotic acid	ChEBI
5,6-Dihydro-orotate	Generator
DL-Dihydroortotate	Generator
Hydroorotate	Generator
4,5-Dihydroorotate	Generator
4,5-Dihydroorotic acid, (D)-isomer	MeSH
4,5-Dihydroorotic acid, (DL)-isomer	MeSH
4,5-Dihydroorotic acid, (L)-isomer	MeSH
5,6-Dihydroorotate	MeSH
L-Dihydroorotate	MeSH
Dihydroorotate	MeSH
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
L-Hydroorotate	HMDB
L-Hydroorotic acid	HMDB
R,S-Hydroorotate	HMDB

Chemical Formula

C₅H₆N₂O₄

Average Molecular Weight

158.1121

Monoisotopic Molecular Weight

158.03275669

IUPAC Name

2,6-dioxo-1,3-diazinane-4-carboxylic acid

Traditional Name

dihydroorotic acid

CAS Registry Number

155-54-4

SMILES

OC(=O)C1CC(=O)NC(=O)N1

InChI Identifier

InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)

InChI Key

UFIVEPVSAGBUSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
N-acyl urea
Pyrimidone
Ureide
1,3-diazinane
Pyrimidine
Dicarboximide
Urea
Carbonic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30865 )
N-acylurea (CHEBI:30865 )
secondary amide (CHEBI:30865 )
pyrimidinemonocarboxylic acid (CHEBI:30865 )

Functional Ontology

Not Available

Prostate (HMDB: HMDB0000528)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000528)

Source

Exogenous

Exogenous (HMDB: HMDB0000528)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000528)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyrimidine Metabolism (PathBank: SMP0121324)
Pyrimidine Metabolism (PathBank: SMP0002370)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	12.7 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.58 m³·mol⁻¹	ChemAxon
Polarizability	13.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000528

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022096

KNApSAcK ID

Not Available

Chemspider ID

628

KEGG Compound ID

C00337

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,5-Dihydroorotic_acid

METLIN ID

5513

PubChem Compound

648

PDB ID

Not Available

ChEBI ID

30865

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Burger, Klaus; Neuhauser, Horst; Rudolph, Martin. A new, preparatively simple way to dihydroorotic acid, 1-methyl-4,5-dihydroorotic acid and their derivatives. Chemiker-Zeitung (1990), 114(7-8), 251-5.

Showing chemical card for 4,5-Dihydroorotic acid (CFc000000406)

MOL for CFc000000406 (4,5-Dihydroorotic acid)

3D MOL for CFc000000406 (4,5-Dihydroorotic acid)

3D SDF for CFc000000406 (4,5-Dihydroorotic acid)

3D-SDF for CFc000000406 (4,5-Dihydroorotic acid)

PDB for CFc000000406 (4,5-Dihydroorotic acid)

3D PDB for CFc000000406 (4,5-Dihydroorotic acid)

SMILES for CFc000000406 (4,5-Dihydroorotic acid)

INCHI for CFc000000406 (4,5-Dihydroorotic acid)

Structure for CFc000000406 (4,5-Dihydroorotic acid)

3D Structure for CFc000000406 (4,5-Dihydroorotic acid)