Livestock Metabolome Database: Showing metabocard for Dihydrouracil (LMDB00033)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:54 UTC

Update Date

2016-07-20 20:54:37 UTC

Lmdb

LMDB00033

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrouracil

Description

Dihydrouracil belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Dihydrouracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrouracil exists in all living organisms, ranging from bacteria to humans. Within humans, dihydrouracil participates in a number of enzymatic reactions. In particular, dihydrouracil can be biosynthesized from uracil; which is mediated by the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In addition, dihydrouracil can be converted into ureidopropionic acid; which is mediated by the enzyme dihydropyrimidinase. In humans, dihydrouracil is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Dihydrouracil has been detected, but not quantified in, several different foods, such as arctic blackberries, garden tomato (var.), sweet potato, star fruits, and adzuki beans. This could make dihydrouracil a potential biomarker for the consumption of these foods. Dihydrouracil is a potentially toxic compound. Dihydrouracil, with regard to humans, has been found to be associated with several diseases such as cerebral infarction, liver disease, colorectal cancer, and hypertension; dihydrouracil has also been linked to the inborn metabolic disorder dihydropyrimidine dehydrogenase deficiency. A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-Dioxotetrahydropyrimidine	ChEBI
5,6-Dihydro-2,4-dihydroxypyrimidine	ChEBI
Dihydro-2,4(1H,3H)-pyrimidinedione	ChEBI
DIHYDROPYRIMIDINE-2,4(1H,3H)-dione	ChEBI
Dihydrouracile	ChEBI
Hydrouracil	ChEBI
5,6-Dihydro-2,4(1H,3H)-pyrimidinedione	HMDB
5,6-Dihydrouracil	HMDB
Dihydro-pyrimidine-2,4-dione	HMDB

Chemical Formula

C₄H₆N₂O₂

Average Molecular Weight

114.1026

Monoisotopic Molecular Weight

114.042927446

IUPAC Name

1,3-diazinane-2,4-dione

Traditional Name

dihydrouracil

CAS Registry Number

504-07-4

SMILES

O=C1CCNC(=O)N1

InChI Identifier

InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

InChI Key

OIVLITBTBDPEFK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrimidone (CHEBI:15901 )
a base derivative (DI-H-URACIL )
a pyrimidine-related compound (DI-H-URACIL )

Ontology

Status

Detected but not 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	-1.3	ALOGPS
logP	-1.2	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	25.75 m³·mol⁻¹	ChemAxon
Polarizability	10.13 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) (2 TMS)	splash10-00di-9700000000-4adeeb2f4f5a1111afb7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00di-5900000000-8af1b81502646fa5b417	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0fdo-9750000000-d2aaeeba1cf962175f84	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-4adeeb2f4f5a1111afb7	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-5900000000-8af1b81502646fa5b417	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fdo-9750000000-d2aaeeba1cf962175f84	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-2940000000-3430a0e2d1819021af1d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-3900000000-79f2d90a419b7469cb61	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9100000000-55536f0571922b6c69fe	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03k9-9800000000-da772cea603c785c1df4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9100000000-94a5f543e8c6be7b3204	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0btc-9200000000-e9bf2ae82714a2a3a737	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-5900000000-0fe83e63f6e5d1347894	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03xr-6900000000-08aca1bc7f27b0e7cb08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-5900000000-53ea361c86b4f9fa284b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-9300000000-a8599c09cd21e2f84329	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-9500000000-03c8b6a5b2dc3625d5d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-331f648f78f506788b99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-824aa91d3f2de539f0bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2900000000-ad7f91d5265e53403dd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0603-9200000000-4b30a83fb454e5bbffb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ce54e3c860a95b0af401	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9800000000-d705e188f6700a76ef72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-a26409d69a4259731004	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f00c4df547660023bee4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-b8f2cf36966bbbbb3285	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9500000000-44775319047d2eddad49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-3cb7005ca8389854848e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-7900000000-9d78d5698ad7865d1789	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-997cffdd9ad85c899225	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a88e812ae86e53f6c2d6	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03fu-9400000000-5b9edda3479e7d0a0d28	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum