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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 19:37:13 UTC

HMDB ID

HMDB0000076

Secondary Accession Numbers

HMDB00076

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 intermediate breakdown product of uracil. Dihydrouracil exists in all living organisms, ranging from bacteria to plants 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(+)]. The breakdown of uracil is a multistep reaction that leads to the production of beta-alanine. The reaction process begins with the enzyme known as dihydropyrimidine dehydrogenase (DHP), which catalyzes the reduction of uracil into dihydrouracil. Then the enzyme known as dihydropyrimidinase hydrolyzes dihydrouracil into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. There is at least one metabolic disorder that is associated with altered levels of dihydrouracil. In particular, dihydropyrimidinase deficiency is an inborn metabolic disorder that leads to highly increased concentrations of dihydrouracil and 5,6-dihydrothymine, and moderately increased concentrations of uracil and thymine in urine. Dihydropyrimidinase deficiency can cause neurological and gastrointestinal problems in some affected individuals (OMIM: 222748 ). In particular, patients with dihydropyrimidinase deficiency exhibit a number of neurological abnormalities including intellectual disability, seizures, weak muscle tone (hypotonia), an abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Physiological effect

Adverse health effect

Carnosinuria (PMID: 24023812 , PMID: 2674258 , PMID: 32966057 )

Genetic disorder

Inborn errors of metabolism

Carnosinemia
Dihydropyrimidinase deficiency (PMID: 17383919 )
Gaba-transaminase deficiency

Circulatory system disorder

Vascular disorder

Hypertension (PMID: 12609766 , PMID: 8232728 , PMID: 8255371 , +38

Source	Link
Pubmed	PMID: 12609766
Pubmed	PMID: 8232728
Pubmed	PMID: 8255371
Pubmed	PMID: 17069347
Pubmed	PMID: 17313719
Pubmed	PMID: 21185973
Pubmed	PMID: 9368807
Pubmed	PMID: 14608088
Pubmed	PMID: 32966057
Pubmed	PMID: 21359215
Pubmed	PMID: 18633173
Pubmed	PMID: 18953024
Pubmed	PMID: 27329611
Pubmed	PMID: 18633173
Pubmed	PMID: 20671299
Pubmed	PMID: 18203893
Pubmed	PMID: 24740205
Pubmed	PMID: 24801555
Pubmed	PMID: 27355821
Pubmed	PMID: 11593343
Pubmed	PMID: 25004141
Pubmed	PMID: 20143319
Pubmed	PMID: 2000815
Pubmed	PMID: 14634727
Pubmed	PMID: 2361977
Pubmed	PMID: 8255371
Pubmed	PMID: 8651468
Pubmed	PMID: 11380830
Pubmed	PMID: 11865286
Pubmed	PMID: 27196457
Pubmed	PMID: 24909877
Pubmed	PMID: 24023812
Pubmed	PMID: 31506554
Pubmed	PMID: 9816152
Pubmed	PMID: 12798197
Pubmed	PMID: 9816152
Pubmed	PMID: 21389975
Pubmed	PMID: 3137238
Pubmed	PMID: 8412012
Pubmed	PMID: 22007635
Pubmed	PMID: 22061338

)

Cerebral infarction (PMID: 32966057 , PMID: 24909877 , PMID: 24023812 , +5

Source	Link
Pubmed	PMID: 32966057
Pubmed	PMID: 24909877
Pubmed	PMID: 24023812
Pubmed	PMID: 31506554
Pubmed	PMID: 9816152
Pubmed	PMID: 12798197
Pubmed	PMID: 9816152
Pubmed	PMID: 21389975

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Organelle

Nucleus

Non-excretory biofluid

Blood
Saliva

Excreta

Feces
Urine

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Nuts

Cocoa and cocoa products

Cocoa

Cocoa bean

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Milk and milk products

Unfermented milks

Milk (Cow)

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	279 - 281 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	25.9 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	122.68	31661259
DarkChem	[M-H]-	115.894	31661259
AllCCS	[M+H]+	124.177	32859911
AllCCS	[M-H]-	119.267	32859911
DeepCCS	[M+H]+	124.729	30932474
DeepCCS	[M-H]-	122.641	30932474
DeepCCS	[M-2H]-	158.592	30932474
DeepCCS	[M+Na]+	133.076	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrouracil	O=C1CCNC(=O)N1	2736.1	Standard polar	33892256
Dihydrouracil	O=C1CCNC(=O)N1	1116.0	Standard non polar	33892256
Dihydrouracil	O=C1CCNC(=O)N1	1385.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrouracil,1TMS,isomer #1	C[Si](C)(C)N1CCC(=O)NC1=O	1414.4	Semi standard non polar	33892256
Dihydrouracil,1TMS,isomer #1	C[Si](C)(C)N1CCC(=O)NC1=O	1472.8	Standard non polar	33892256
Dihydrouracil,1TMS,isomer #1	C[Si](C)(C)N1CCC(=O)NC1=O	2379.2	Standard polar	33892256
Dihydrouracil,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CCNC1=O	1363.6	Semi standard non polar	33892256
Dihydrouracil,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CCNC1=O	1393.6	Standard non polar	33892256
Dihydrouracil,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CCNC1=O	2353.8	Standard polar	33892256
Dihydrouracil,2TMS,isomer #1	C[Si](C)(C)N1CCC(=O)N([Si](C)(C)C)C1=O	1393.2	Semi standard non polar	33892256
Dihydrouracil,2TMS,isomer #1	C[Si](C)(C)N1CCC(=O)N([Si](C)(C)C)C1=O	1500.3	Standard non polar	33892256
Dihydrouracil,2TMS,isomer #1	C[Si](C)(C)N1CCC(=O)N([Si](C)(C)C)C1=O	1894.2	Standard polar	33892256
Dihydrouracil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)NC1=O	1688.2	Semi standard non polar	33892256
Dihydrouracil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)NC1=O	1727.5	Standard non polar	33892256
Dihydrouracil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)NC1=O	2598.1	Standard polar	33892256
Dihydrouracil,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CCNC1=O	1640.6	Semi standard non polar	33892256
Dihydrouracil,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CCNC1=O	1635.2	Standard non polar	33892256
Dihydrouracil,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CCNC1=O	2419.8	Standard polar	33892256
Dihydrouracil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1849.1	Semi standard non polar	33892256
Dihydrouracil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1978.0	Standard non polar	33892256
Dihydrouracil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2074.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9700000000-4adeeb2f4f5a1111afb7	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-MS (1 TMS)	splash10-00di-5900000000-8af1b81502646fa5b417	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-MS (2 TMS)	splash10-0fdo-9750000000-d2aaeeba1cf962175f84	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-4adeeb2f4f5a1111afb7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-MS (Non-derivatized)	splash10-00di-5900000000-8af1b81502646fa5b417	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-MS (Non-derivatized)	splash10-0fdo-9750000000-d2aaeeba1cf962175f84	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-EI-TOF (Non-derivatized)	splash10-0f6w-2940000000-3430a0e2d1819021af1d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydrouracil GC-EI-TOF (Non-derivatized)	splash10-00di-3900000000-79f2d90a419b7469cb61	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrouracil GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9100000000-55536f0571922b6c69fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrouracil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03fu-9400000000-5b9edda3479e7d0a0d28	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03k9-9800000000-da772cea603c785c1df4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9100000000-94a5f543e8c6be7b3204	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0btc-9200000000-e9bf2ae82714a2a3a737	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-014i-5900000000-0fe83e63f6e5d1347894	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil , negative-QTOF	splash10-03xr-6900000000-08aca1bc7f27b0e7cb08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil LC-ESI-QTOF , positive-QTOF	splash10-014i-5900000000-53ea361c86b4f9fa284b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil , positive-QTOF	splash10-00di-9300000000-a8599c09cd21e2f84329	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil 10V, Positive-QTOF	splash10-01b9-9500000000-03c8b6a5b2dc3625d5d3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil 20V, Positive-QTOF	splash10-0ab9-9000000000-331f648f78f506788b99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrouracil 40V, Positive-QTOF	splash10-052f-9000000000-824aa91d3f2de539f0bd	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 10V, Positive-QTOF	splash10-014i-2900000000-ad7f91d5265e53403dd6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 20V, Positive-QTOF	splash10-0603-9200000000-4b30a83fb454e5bbffb8	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 40V, Positive-QTOF	splash10-0006-9000000000-ce54e3c860a95b0af401	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 10V, Negative-QTOF	splash10-03di-9800000000-d705e188f6700a76ef72	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 20V, Negative-QTOF	splash10-0006-9000000000-a26409d69a4259731004	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 40V, Negative-QTOF	splash10-0006-9000000000-f00c4df547660023bee4	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 10V, Positive-QTOF	splash10-014i-0900000000-b8f2cf36966bbbbb3285	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 20V, Positive-QTOF	splash10-014i-9500000000-44775319047d2eddad49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 40V, Positive-QTOF	splash10-052f-9000000000-3cb7005ca8389854848e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 10V, Negative-QTOF	splash10-03dl-7900000000-9d78d5698ad7865d1789	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 20V, Negative-QTOF	splash10-0006-9000000000-997cffdd9ad85c899225	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrouracil 40V, Negative-QTOF	splash10-0006-9000000000-a88e812ae86e53f6c2d6	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Nucleus

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Fibroblasts
Kidney
Liver
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Pyrimidine metabolism	Not Available
beta-Alanine metabolism	Not Available
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.31 (0.02-1.63) uM	Adult (>18 years old)	Female	Normal	11936689	details
Blood	Detected and Quantified	0.31 (0.02-1.63) uM	Adult (>18 years old)	Both	Normal	11936689	details
Blood	Detected and Quantified	0.32 ( 0.10-0.74) uM	Adult (>18 years old)	Male	Normal	11936689	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.1 +/- 1.0 uM	Adult (>18 years old)	Not Specified	Normal	15385443	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	700 +/- 199 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2168.16 +/- 127.94 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	2000 +/- 223 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2000 +/- 223 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2210 +/- 353 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2240 +/- 380 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2350 +/- 654 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.79 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12798197	details
Urine	Detected and Quantified	3.8 (2.1-8.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.4 +/- 4.7 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9816152	details
Urine	Detected and Quantified	3.0 +/- 2.7 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9816152	details
Urine	Detected and Quantified	2.5-20 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	12.2 +/- 6.2 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8581129	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	<3.4 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	81.5 (46.0-117.0) uM	Adult (>18 years old)	Both	Dihydropyrimidine dehydrogenase (DPD) deficiency	14705962	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	2.4 +/- 1.67 umol/mmol creatinine	Adult (>18 years old)	Both	Hypertension	9816152	details
Urine	Detected and Quantified	627.0 umol/mmol creatinine	Infant (0-1 year old)	Both	Dihydropyrimidine dehydrogenase (DPD) deficiency	8581129	details
Urine	Detected and Quantified	2.4 +/- 2.00 umol/mmol creatinine	Adult (>18 years old)	Both	Cerebral infarction	9816152	details
Urine	Detected and Quantified	2.8 +/- 1.9 umol/mmol creatinine	Adult (>18 years old)	Both	Malignancy	9816152	details
Urine	Detected and Quantified	2.7 +/- 1.9 umol/mmol creatinine	Adult (>18 years old)	Both	Liver dysfunction	9816152	details
Urine	Detected and Quantified	2.5 +/- 2.00 umol/mmol creatinine	Adult (>18 years old)	Both	Nephropathy	9816152	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Dihydropyrimidine dehydrogenase deficiency
Sumi S, Kidouchi K, Ohba S, Wada Y: Automated screening system for purine and pyrimidine metabolism disorders using high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Oct 20;672(2):233-9. [PubMed:8581129 ] Van Kuilenburg AB, Stroomer AE, Van Lenthe H, Abeling NG, Van Gennip AH: New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid? Biochem J. 2004 Apr 1;379(Pt 1):119-24. [PubMed:14705962 ]
Hypertension
Hayashi K, Kidouchi K, Sumi S, Mizokami M, Orito E, Kumada K, Ueda R, Wada Y: Possible prediction of adverse reactions to pyrimidine chemotherapy from urinary pyrimidine levels and a case of asymptomatic adult dihydropyrimidinuria. Clin Cancer Res. 1996 Dec;2(12):1937-41. [PubMed:9816152 ]
Cerebral infarction
Hayashi K, Kidouchi K, Sumi S, Mizokami M, Orito E, Kumada K, Ueda R, Wada Y: Possible prediction of adverse reactions to pyrimidine chemotherapy from urinary pyrimidine levels and a case of asymptomatic adult dihydropyrimidinuria. Clin Cancer Res. 1996 Dec;2(12):1937-41. [PubMed:9816152 ]
Liver disease
Hayashi K, Kidouchi K, Sumi S, Mizokami M, Orito E, Kumada K, Ueda R, Wada Y: Possible prediction of adverse reactions to pyrimidine chemotherapy from urinary pyrimidine levels and a case of asymptomatic adult dihydropyrimidinuria. Clin Cancer Res. 1996 Dec;2(12):1937-41. [PubMed:9816152 ]

Associated OMIM IDs

114500 (Colorectal cancer)
274270 (Dihydropyrimidine dehydrogenase deficiency)
145500 (Hypertension)

External Links

DrugBank ID

DB01849

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030556

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15901

Food Biomarker Ontology

Not Available

VMH ID

56DURA

MarkerDB ID

MDB00000040

Good Scents ID

Not Available

References

Synthesis Reference

Bhat, K. S.; Rao, A. S. Synthesis of uracil, 6-methyluracil and some dihydrouracils. Organic Preparations and Procedures International (1983), 15(5), 303-13.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. [PubMed:12798197 ]
Van Kuilenburg AB, Stroomer AE, Van Lenthe H, Abeling NG, Van Gennip AH: New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid? Biochem J. 2004 Apr 1;379(Pt 1):119-24. [PubMed:14705962 ]
Grem JL: Intratumoral molecular or genetic markers as predictors of clinical outcome with chemotherapy in colorectal cancer. Semin Oncol. 2005 Feb;32(1):120-7. [PubMed:15726514 ]
Assmann B, Hoffmann GF, Wagner L, Brautigam C, Seyberth HW, Duran M, Van Kuilenburg AB, Wevers R, Van Gennip AH: Dihydropyrimidinase deficiency and congenital microvillous atrophy: coincidence or genetic relation? J Inherit Metab Dis. 1997 Sep;20(5):681-8. [PubMed:9323563 ]
Megyeri A, Bacso Z, Shields A, Eliason JF: Development of a stereological method to measure levels of fluoropyrimidine metabolizing enzymes in tumor sections using laser scanning cytometry. Cytometry A. 2005 Apr;64(2):62-71. [PubMed:15729713 ]
Nakamura A, Kikuchi K, Ohishi T, Masuike T: [Assay method for uracil, dihydrouracil, 5-fluorouracil and 5-fluoro-5, 6-dihydrouracil by high-performance liquid chromatography]. Gan To Kagaku Ryoho. 2004 Mar;31(3):381-6. [PubMed:15045945 ]
van Lenthe H, van Kuilenburg AB, Ito T, Bootsma AH, van Cruchten A, Wada Y, van Gennip AH: Defects in pyrimidine degradation identified by HPLC-electrospray tandem mass spectrometry of urine specimens or urine-soaked filter paper strips. Clin Chem. 2000 Dec;46(12):1916-22. [PubMed:11106323 ]
Sumi S, Kidouchi K, Ohba S, Wada Y: Automated screening system for purine and pyrimidine metabolism disorders using high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Oct 20;672(2):233-9. [PubMed:8581129 ]
Shen GP, Galick H, Inoue M, Wallace SS: Decline of nuclear and mitochondrial oxidative base excision repair activity in late passage human diploid fibroblasts. DNA Repair (Amst). 2003 Jun 11;2(6):673-93. [PubMed:12767347 ]
Tan BR, McLeod HL: Pharmacogenetic influences on treatment response and toxicity in colorectal cancer. Semin Oncol. 2005 Feb;32(1):113-9. [PubMed:15726513 ]
Garcia AA, Blessing JA, Lenz HJ, Darcy KM, Mannel RS, Miller DS, Husseinzadeh N: Phase II clinical trial of capecitabine in ovarian carcinoma recurrent 6-12 months after completion of primary chemotherapy, with exploratory TS, DPD, and TP correlates: a Gynecologic Oncology Group study. Gynecol Oncol. 2005 Mar;96(3):810-7. [PubMed:15721430 ]
Schneider S, Uchida K, Brabender J, Baldus SE, Yochim J, Danenberg KD, Salonga D, Chen P, Tsao-Wei D, Groshen S, Hoelscher AH, Schneider PM, Danenberg PV: Downregulation of TS, DPD, ERCC1, GST-Pi, EGFR, and HER2 gene expression after neoadjuvant three-modality treatment in patients with esophageal cancer. J Am Coll Surg. 2005 Mar;200(3):336-44. [PubMed:15737843 ]
Jiang H, Jiang J, Hu P, Hu Y: Measurement of endogenous uracil and dihydrouracil in plasma and urine of normal subjects by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Mar 25;769(1):169-76. [PubMed:11936689 ]

Enzymes

Enzyme Details

1. Dihydropyrimidinase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
Gene Name:: DPYS
Uniprot ID:: Q14117
Molecular weight:: 56629.36

Reactions

Dihydrouracil + Water → Ureidopropionic acid	details

Enzyme Details

2. Dihydropyrimidine dehydrogenase [NADP(+)]

General function:: Involved in electron carrier activity
Specific function:: Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name:: DPYD
Uniprot ID:: Q12882
Molecular weight:: 111400.32

Reactions

Dihydrouracil + NADP → Uracil + NADPH	details
Dihydrouracil + NADP → Uracil + NADPH + Hydrogen Ion	details

Showing metabocard for Dihydrouracil (HMDB0000076)

MOL for HMDB0000076 (Dihydrouracil)

3D MOL for HMDB0000076 (Dihydrouracil)

3D SDF for HMDB0000076 (Dihydrouracil)

3D-SDF for HMDB0000076 (Dihydrouracil)

PDB for HMDB0000076 (Dihydrouracil)

3D PDB for HMDB0000076 (Dihydrouracil)

SMILES for HMDB0000076 (Dihydrouracil)

INCHI for HMDB0000076 (Dihydrouracil)

Structure for HMDB0000076 (Dihydrouracil)

3D Structure for HMDB0000076 (Dihydrouracil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions