Milk Composition Database: Showing metabocard for Orotic acid (BMDB0000226)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:03 UTC

Update Date

2020-06-04 21:02:30 UTC

MCDB ID

BMDB0000226

Secondary Accession Numbers

BMDB00226

Metabolite Identification

Common Name

Orotic acid

Description

Orotic acid, also known as orotate or orotsaeure, 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. Orotic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Orotic acid exists in all living species, ranging from bacteria to humans. Orotic acid is a potentially toxic compound. Orotic acid has been found to be associated with several diseases known as colorectal cancer, ulcerative colitis, canavan disease, and crohn's disease; also orotic acid has been linked to the inborn metabolic disorders including lysinuric protein intolerance.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	345.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.82 mg/mL at 18 °C	Not Available
LogP	-0.83	SANGSTER (1994)

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfr-2693000000-07bf11b5177412647d9b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1982000000-b20f2ec9a2f1acc84ae1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-2693000000-07bf11b5177412647d9b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1972000000-c04fb7381d3ca07c9b0a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06ri-6900000000-4ba5fde1f8f62c4a2ba2	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0229-9850000000-8164142820eb5162e753	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-0900000000-81d73aed73c250fff3ae	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9300000000-ecb08d1854a2789480d1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9100000000-15748a4c13636c42f4f9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-02ti-4900000000-6fd6312d81f94faaaf11	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-1b7abf52e4a01cb85541	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-1b7abf52e4a01cb85541	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03di-0900000000-3dff3caa5c10aff8ce46	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-02ti-4900000000-6fd6312d81f94faaaf11	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-351f585d58b38f6132de	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0900000000-4e46209ca236b470bf7f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9300000000-aa9cd31d715d134ee8dd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-cdd01e740b6f9d1a909a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-baf39ad8ab6f08fb1a7b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0900000000-1ad59feda583f2247b21	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-0d0d27215e9f39a2a15b	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-918a38777f5d4e049697	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-7900000000-303fe3e06e98f518a2ee	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b2c02975bbba65c2f1c6	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-0900000000-1ad59feda583f2247b21	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-0d0d27215e9f39a2a15b	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-918a38777f5d4e049697	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-d7bbee7f2dc7bb0c6a83	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-7900000000-303fe3e06e98f518a2ee	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b2c02975bbba65c2f1c6	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-066r-9300000000-e5c3ef3304f93a38628c	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	783 uM	PMID: 1958838	details
Detected and Quantified	845 uM	PMID: 1958838	details
Detected and Quantified	124 uM	PMID: 1958838	details
Detected and Quantified	618 +/- 233 uM	PMID: 1958838	details
Detected and Quantified	700 - 1200 uM	PMID: 3755899	details
Detected and Quantified	578 uM	PMID: 6539345	details
Detected and Quantified	53 uM	PMID: 6547459	details
Detected and Quantified	515 uM	PMID: 6547459	details
Detected and Quantified	49 - 419 uM	PMID: 7196410	details
Detected and Quantified	192 - 448 uM	PMID: 15084094	details
Detected and Quantified	418 uM	PMID: 18629683	details
Detected and Quantified	257 +/- 4 uM	Carbohydrate Poly...	details
Detected but not Quantified	Not Applicable	PMID: 23394630	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	PMID: 23182357	details
Detected but not Quantified	Not Applicable	PMID: 25087032	details
Detected and Quantified	208 - 1002 uM	PMID: 22098372	details
Detected and Quantified	511 +/- 45 uM	PMID: 30994344	details
Detected and Quantified	542 +/- 18 uM	PMID: 30994344	details
Detected and Quantified	536 +/- 19 uM	PMID: 30994344	details
Detected and Quantified	565 +/- 49 uM	PMID: 30994344	details
Detected and Quantified	581 +/- 134 uM	PMID: 29642378	details
Detected and Quantified	487 +/- 178 uM	PMID: 29642378	details
Detected and Quantified	542 +/- 166 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000226

DrugBank ID

DB02262

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16742

References

Synthesis Reference

Mitchell, Herschel K.; Nyc, Joseph F. Intermediates in the synthesis of orotic acid from oxalacetic ester and urea. Journal of the American Chemical Society (1947), 69 674-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82. [PubMed:1958838 ]
Motyl T, Barej W, Leontowicz H: The orotic acid concentration in the blood, milk, and urine of dairy cows fed with urea supplemented diet. Arch Tierernahr. 1986 Jun;36(6):551-6. [PubMed:3755899 ]
Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
Robinson JL, Dombrowski DB, Clark JH, Shanks RD: Orotate in milk and urine of dairy cows with a partial deficiency of uridine monophosphate synthase. J Dairy Sci. 1984 May;67(5):1024-9. doi: 10.3168/jds.S0022-0302(84)81401-0. [PubMed:6547459 ]
Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44. [PubMed:7196410 ]
Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22. [PubMed:15084094 ]
Karatas F, Aydin S, Kaygusuzoglu E, Yildiz H, Erulas FA, Ozkan Y: Ghrelin and orotic acid increased in subclinical mastitis. Arch Physiol Biochem. 2008 Jul;114(3):178-82. doi: 10.1080/13813450802180940 . [PubMed:18629683 ]
Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. [PubMed:23394630 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
I.M.P.L.V.O Ferreira, A.M.P Gomes, M.A Ferreira (1998). Carbohydrate Polymers 37 (1998) 225-229. Carbohydrate Polymers.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Orotic acid (BMDB0000226)

Structure for BMDB0000226 (Orotic acid)