Milk Composition Database: Showing metabocard for Urea (BMDB0000294)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:58 UTC

Update Date

2020-06-04 21:45:44 UTC

MCDB ID

BMDB0000294

Secondary Accession Numbers

BMDB00294

Metabolite Identification

Common Name

Urea

Description

Urea, also known as ur or carbamide, belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Urea exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Urea exists in all living species, ranging from bacteria to humans. Urea is a potentially toxic compound. Urea has been found to be associated with several diseases known as cirrhosis, tuberculous meningitis, perillyl alcohol administration for cancer treatment, and bartter syndrome, type 2, antenatal; also urea has been linked to the inborn metabolic disorders including cholesteryl ester storage disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1728	ChEBI
Carbamide	ChEBI
Carbonyldiamide	ChEBI
e927b	ChEBI
H2NC(O)NH2	ChEBI
Harnstoff	ChEBI
Karbamid	ChEBI
ur	ChEBI
Uree	ChEBI
Pastaron	Kegg
Alphadrate	HMDB
ARF	HMDB
b-I-K	HMDB
beta-I-K	HMDB
Bromisovalum	HMDB
Bubber shet	HMDB
Calmurid	HMDB
Calmurid HC	HMDB
Carbaderm	HMDB
Carbamide resin	HMDB
Carbonyl diamide	HMDB
Carbonyl diamine	HMDB
Carbonyldiamine	HMDB
Carmol	HMDB
Helicosol	HMDB
Hyanit	HMDB
Isourea	HMDB
Keratinamin	HMDB
Keratinamin kowa	HMDB
Mocovina	HMDB
Onychomal	HMDB
Panafil	HMDB
URE	HMDB
Ureaphil	HMDB
Ureophil	HMDB
Basodexan	HMDB

Chemical Formula

CH₄N₂O

Average Molecular Weight

60.0553

Monoisotopic Molecular Weight

60.03236276

IUPAC Name

urea

Traditional Name

urea

CAS Registry Number

57-13-6

SMILES

NC(N)=O

InChI Identifier

InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)

InChI Key

XSQUKJJJFZCRTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Ureas

Alternative Parents

Substituents

Urea
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:48376 )
isourea (CHEBI:48376 )
a small molecule (UREA )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	132 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	545 mg/mL	Not Available
LogP	-2.11	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-1.4	ChemAxon
logS	0.84	ALOGPS
pKa (Strongest Acidic)	15.73	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.11 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	13.14 m³·mol⁻¹	ChemAxon
Polarizability	5.1 Å³	ChemAxon
Number of Rings	0	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)	splash10-0002-0900000000-234545ed5860ba077237	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0079-3900000000-0ef80e5f5cd9dd6bd213	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-02tc-9000000000-d69da17ffbb84fb6bdca	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-234545ed5860ba077237	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0079-3900000000-0ef80e5f5cd9dd6bd213	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1900000000-d805e3019d86aaf9fec0	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9000000000-400d59bf59b857bd7c06	2016-09-22	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9000000000-8f09c5d6f5e002dfa52e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03dl-9000000000-3d983e9f9115869f55c8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-9404d66c59d266164c23	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-03di-9000000000-828ab6c68e3a46ccbd88	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-9000000000-91554974873c3217dc93	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-03di-9000000000-9d3431eab9093f365e2b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-4bdf0d3bd74007ba840a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-7184b34bac3a316d9fea	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-37fd015e8c20febde95a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-2fc4ec950c571662bb31	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9000000000-3443c9c73d9a3f03e398	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-11d83d6bda76c25ec73f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052f-9000000000-39cd266ec67397ab213f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-9000000000-95a1106bd10162ddd326	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-b759ce75f0e73d2777db	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fd9f25340762315b4515	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-02tc-9000000000-871569893ccfa5dd5395	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone+DMSO+tetramethylurea, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	4329 uM	PMID: 12146486	details
Detected and Quantified	2331 - 2381 uM	PMID: 19841222	details
Detected and Quantified	5944 - 6144 uM	PMID: 19841222	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details
Detected but not Quantified	Not Applicable	PMID: 25108860	details
Detected and Quantified	4110 uM	PMID: 9718493	details
Detected and Quantified	4570 uM	PMID: 9718493	details
Detected and Quantified	5150 uM	PMID: 9718493	details
Detected and Quantified	6130 uM	PMID: 9718493	details
Detected and Quantified	6450 uM	PMID: 9718493	details
Detected and Quantified	6490 uM	PMID: 9718493	details
Detected and Quantified	6570 uM	PMID: 9718493	details
Detected and Quantified	6850 uM	PMID: 9718493	details
Detected and Quantified	6890 uM	PMID: 9718493	details
Detected and Quantified	7160 uM	PMID: 9718493	details
Detected and Quantified	7310 uM	PMID: 9718493	details
Detected and Quantified	7480 uM	PMID: 9718493	details
Detected and Quantified	2250 +/- 140 uM	PMID: 23040012	details
Detected and Quantified	2250 +/- 300 uM	PMID: 23040012	details
Detected and Quantified	2460 +/- 170 uM	PMID: 23040012	details
Detected and Quantified	2700 +/- 120 uM	PMID: 23040012	details
Detected and Quantified	2930 +/- 110 uM	PMID: 23040012	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	1117 +/- 175 uM	PMID: 30994344	details
Detected and Quantified	1174 +/- 115 uM	PMID: 30994344	details
Detected and Quantified	1115 +/- 30 uM	PMID: 30994344	details
Detected and Quantified	1104 +/- 136 uM	PMID: 30994344	details
Detected and Quantified	222 +/- 103 uM	PMID: 29642378	details
Detected and Quantified	389 +/- 58 uM	PMID: 29642378	details
Detected and Quantified	282 +/- 45 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0000294

DrugBank ID

DB03904

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

1176

PDB ID

Not Available

ChEBI ID

16199

References

Synthesis Reference

Leuthardt, F.; Glasson, B. Biological synthesis of urea. Verhandl. Ver. schweiz. Physiol. (1942), 21 25-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Korhonen M, Vanhatalo A, Huhtanen P: Evaluation of isoleucine, leucine, and valine as a second-limiting amino acid for milk production in dairy cows fed grass silage diet. J Dairy Sci. 2002 Jun;85(6):1533-45. doi: 10.3168/jds.S0022-0302(02)74223-9. [PubMed:12146486 ]
Vanhatalo A, Kuoppala K, Ahvenjarvi S, Rinne M: Effects of feeding grass or red clover silage cut at two maturity stages in dairy cows. 1. Nitrogen metabolism and supply of amino acids. J Dairy Sci. 2009 Nov;92(11):5620-33. doi: 10.3168/jds.2009-2249. [PubMed:19841222 ]
Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3. [PubMed:23040012 ]
Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
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 ]
Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
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 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
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 Urea (BMDB0000294)

Structure for BMDB0000294 (Urea)