P. aeruginosa Metabolome Database: 4,5-Dihydroorotic acid (PAMDB000147)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000147

Identification

Name:

4,5-Dihydroorotic acid

Description:

4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC 1.3.1.14], which is part of the pyrimidine metabolism pathway. (KEGG) Dihydroorotate is oxidized by Dihydroorotate dehydrogenases (DHODs) to orotate. These dehydrogenases use their FMN (flavin mononucleotide) prosthetic group to abstract a hydride equivalent from C6 to deprotonate C5

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
(S)-4,5-dihydroorotate
(S)-4,5-dihydroorotic acid
(S)-4-pyrimidinecarboxylic acid
(S)-di-H-orotate
(S)-hydroorotic acid
(R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
(S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
(S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
(S)-4,5-Dihydroorotate
(S)-4,5-dihydroorotic acid
(S)-4-pyrimidinecarboxylate
(S)-4-pyrimidinecarboxylic acid
(S)-di-H-orotate
(S)-di-H-orotic acid
(S)-Dihydroorotate
(S)-Dihydroorotic acid
(S)-hydroorotate
(S)-hydroorotic acid
2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
4,5-Dihydro-L-orotate
4,5-Dihydro-L-orotic acid
4,5-Dihydroorotate
4,5-Dihydroorotic acid
5,6-Dihydroorotate
5,6-Dihydroorotic acid
Dihydro-L-orotate
Dihydro-L-orotic acid
L-4,5-Dihydroorotate
L-4,5-Dihydroorotic acid
L-Dihydroorotate
L-Dihydroorotic acid
L-Hydroorotate
L-Hydroorotic acid
R,S-Hydroorotate
R,S-Hydroorotic acid

Chemical Formula:

C₅H₆N₂O₄

Average Molecular Weight:

158.1121

Monoisotopic Molecular Weight:

158.03275669

InChI Key:

UFIVEPVSAGBUSI-UHFFFAOYSA-N

InChI:

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)

CAS number:

155-54-4

IUPAC Name:

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

Traditional IUPAC Name:

dihydroorotic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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
Ureide
Pyrimidone
Pyrimidine
1,3-diazinane
Urea
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	12.7 mg/mL	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	13.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Metabolic pathways pae01100
Pyrimidine metabolism pae00240

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-059i-9700000000-c8ce0433c02db41880b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-56601203ef19b09212fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-006x-9000000000-b6342346ce51dd871eaa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411

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.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	30865
HMDB ID	HMDB00528
Pubchem Compound ID	648
Kegg ID	C00337
ChemSpider ID	628
Wikipedia	4,5-Dihydroorotic acid
BioCyc ID	DI-H-OROTATE
EcoCyc ID	DI-H-OROTATE

4,5-Dihydroorotic acid (PAMDB000147)

Structure for 4,5-Dihydroorotic acid (PAMDB000147)