Livestock Metabolome Database: Showing metabocard for Orotic acid (LMDB00106)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:29 UTC

Update Date

2016-09-23 18:44:41 UTC

Lmdb

LMDB00106

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Orotic acid

Description

Orotic acid is a minor dietary constituent. Indeed, until it was realized that it could be synthesized by animals, orotic acid was known as vitamin B-13. The richest dietary sources are cow's milk and other dairy products as well as root vegetables such as carrots and beets. Dietary intake probably contributes to a basal rate of orotic acid excretion in urine because fasting decreases excretion by ~50%. However, it is now apparent that most urinary orotic acid is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyltransferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase. This disorder prevents the conversion of orotic acid to UMP and thus to other pyrimidines. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Indeed, urinary orotic acid is so markedly increased in individuals harboring a mutation in UMP synthase that orotic acid crystals can form in the urine. The urinary concentration of orotic acid in homozygotes can be of the order of millimoles per millimole creatinine. By comparison, the urinary level in unaffected individuals is ~ 1 umol/mmol creatinine. (PMID: 17513443 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Orotsaeure	ChEBI
Uracil-6-carboxylic acid	ChEBI
Uracil-6-carboxylate	Generator
Orotate	Generator
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid	HMDB
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid	HMDB
1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure	HMDB
2,6-Dihydroxy-4-pyrimidinecarboxylic acid	HMDB
2,6-Dihydroxypyrimidine-4-carboxylic acid	HMDB
2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid	HMDB
2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid	HMDB
6-Carboxy-2,4-dihydroxypyrimidine	HMDB
6-Carboxyuracil	HMDB
6-Uracilcarboxylic acid	HMDB
Acide orotique	HMDB
Acido orotico	HMDB
Acidum oroticum	HMDB
Animal galactose factor	HMDB
Lactinium	HMDB
Molkensaeure	HMDB
ORO	HMDB
Orodin	HMDB
Oropur	HMDB
Orotonin	HMDB
Orotonsan	HMDB
Orotsaure	HMDB
Oroturic	HMDB
Orotyl	HMDB
Uracil-6-carbosaeure	HMDB
Vitamin b13	HMDB
Whey factor	HMDB
Zinc orotate	HMDB
Orotate, zinc	HMDB
Acid, orotic	HMDB
Orotate, potassium	HMDB
Potassium orotate	HMDB
Orotate, sodium	HMDB
Sodium orotate	HMDB

Chemical Formula

C₅H₄N₂O₄

Average Molecular Weight

156.0963

Monoisotopic Molecular Weight

156.017106626

IUPAC Name

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

Traditional Name

orotic acid

CAS Registry Number

65-86-1

SMILES

OC(=O)C1=CC(=O)NC(=O)N1

InChI Identifier

InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)

InChI Key

PXQPEWDEAKTCGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidinecarboxylic acids

Alternative Parents

Substituents

Pyrimidine-6-carboxylic acid
Hydropyrimidine carboxylic acid derivative
Pyrimidone
Hydropyrimidine
Heteroaromatic compound
Vinylogous amide
Urea
Lactam
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidinemonocarboxylic acid (CHEBI:16742 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.89	ALOGPS
logP	-1.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	-6	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	33.27 m³·mol⁻¹	ChemAxon
Polarizability	12.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-1982000000-b20f2ec9a2f1acc84ae1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfr-2693000000-07bf11b5177412647d9b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1982000000-b20f2ec9a2f1acc84ae1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-2693000000-07bf11b5177412647d9b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1972000000-c04fb7381d3ca07c9b0a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06ri-6900000000-4ba5fde1f8f62c4a2ba2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0229-9850000000-8164142820eb5162e753	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-0900000000-81d73aed73c250fff3ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9300000000-ecb08d1854a2789480d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9100000000-15748a4c13636c42f4f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-02ti-4900000000-6fd6312d81f94faaaf11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-1b7abf52e4a01cb85541	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-1b7abf52e4a01cb85541	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03di-0900000000-3dff3caa5c10aff8ce46	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-02ti-4900000000-6fd6312d81f94faaaf11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-351f585d58b38f6132de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0900000000-4e46209ca236b470bf7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9300000000-aa9cd31d715d134ee8dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-cdd01e740b6f9d1a909a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-baf39ad8ab6f08fb1a7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0900000000-1ad59feda583f2247b21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-0d0d27215e9f39a2a15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-918a38777f5d4e049697	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-7900000000-303fe3e06e98f518a2ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b2c02975bbba65c2f1c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0900000000-1ad59feda583f2247b21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-0d0d27215e9f39a2a15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-918a38777f5d4e049697	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-7900000000-303fe3e06e98f518a2ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b2c02975bbba65c2f1c6	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-066r-9300000000-e5c3ef3304f93a38628c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23394630	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Milk	Detected and Quantified	208-1002 uM	Not Available	Bovine	22098372	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details