You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Dihydrouracil (HMDB0000076)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 19:37:13 UTC
HMDB IDHMDB0000076
Secondary Accession Numbers
  • HMDB00076
Metabolite Identification
Common NameDihydrouracil
DescriptionDihydrouracil 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
Data?1582752110
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000076 (Dihydrouracil)


  Mrv1652305271900092D          

  8  8  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000076 (Dihydrouracil)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -0.5058   -2.5470   -0.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346   -1.3884    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601   -0.3666    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8965    0.8207   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    1.3330   -0.1403 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927    0.4261    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652    0.8322    0.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2194   -0.9673    0.1531 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -0.7595    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -0.0077    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902    1.5633   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    0.4311   -1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930    2.3293   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618   -1.6990    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  8 14  1  0
M  END
Download

3D SDF for HMDB0000076 (Dihydrouracil)


  Mrv1652305271900092D          

  8  8  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000076

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.1026

> <EXACT_MASS>
114.042927446

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.133629968746801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-diazinane-2,4-dione

> <ALOGPS_LOGP>
-1.28

> <JCHEM_LOGP>
-1.2132077313333332

> <ALOGPS_LOGS>
-0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.605544735996883

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.726846896036472

> <JCHEM_PKA_STRONGEST_BASIC>
-7.628772459765097

> <JCHEM_POLAR_SURFACE_AREA>
58.2

> <JCHEM_REFRACTIVITY>
25.745500000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrouracil

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000076 (Dihydrouracil)

https://cactus.nci.nih.gov/chemical/structure/O=C1CCNC(=O)N1/file?format=sdf&...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:13})
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.2238   -0.9877    0.1140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1839   -0.3845   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    1.0861   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    1.7700    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020    0.9812    0.0310 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -0.3606   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -0.9874   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -1.0254    0.0867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548    1.2153   -1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    1.5300    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    2.7677   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    1.8475    1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475    1.4341   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.9836    0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
$$$$
Download

PDB for HMDB0000076 (Dihydrouracil)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for HMDB0000076 (Dihydrouracil)

COMPND    https://cactus.nci.nih.gov/chemical/structure/O=C1CCNC(=O)N1/file?format=sdf&... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1      -2.224  -0.988   0.114  1.00  0.00           O  
HETATM    2  C   UNL     1      -1.184  -0.385  -0.043  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.208   1.086  -0.376  1.00  0.00           C  
HETATM    4  C   UNL     1      -0.006   1.770   0.280  1.00  0.00           C  
HETATM    5  N   UNL     1       1.202   0.981   0.031  1.00  0.00           N  
HETATM    6  C   UNL     1       1.156  -0.361  -0.001  1.00  0.00           C  
HETATM    7  O   UNL     1       2.192  -0.987  -0.105  1.00  0.00           O  
HETATM    8  N   UNL     1      -0.008  -1.025   0.087  1.00  0.00           N  
HETATM    9  H   UNL     1      -1.155   1.215  -1.457  1.00  0.00           H  
HETATM   10  H   UNL     1      -2.129   1.530   0.000  1.00  0.00           H  
HETATM   11  H   UNL     1       0.118   2.768  -0.141  1.00  0.00           H  
HETATM   12  H   UNL     1      -0.174   1.847   1.354  1.00  0.00           H  
HETATM   13  H   UNL     1       2.047   1.434  -0.114  1.00  0.00           H  
HETATM   14  H   UNL     1      -0.001  -1.984   0.237  1.00  0.00           H  
CONECT    1    2    2                                                 
CONECT    2    1    1    3    8                                       
CONECT    3    2    4    9   10                                       
CONECT    4    3    5   11   12                                       
CONECT    5    4    6   13                                            
CONECT    6    5    7    7    8                                       
CONECT    7    6    6                                                 
CONECT    8    6    2   14                                            
CONECT    9    3                                                      
CONECT   10    3                                                      
CONECT   11    4                                                      
CONECT   12    4                                                      
CONECT   13    5                                                      
CONECT   14    8                                                      
MASTER        0    0    0    0    0    0    0    0   14    0   14    0
END
Download

SMILES for HMDB0000076 (Dihydrouracil)

O=C1CCNC(=O)N1
Download

INCHI for HMDB0000076 (Dihydrouracil)

InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
2,4-DioxotetrahydropyrimidineChEBI
5,6-Dihydro-2,4-dihydroxypyrimidineChEBI
Dihydro-2,4(1H,3H)-pyrimidinedioneChEBI
DIHYDROPYRIMIDINE-2,4(1H,3H)-dioneChEBI
DihydrouracileChEBI
HydrouracilChEBI
5,6-Dihydro-2,4(1H,3H)-pyrimidinedioneHMDB
5,6-DihydrouracilHMDB
Dihydro-pyrimidine-2,4-dioneHMDB
Chemical FormulaC4H6N2O2
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
IUPAC Name1,3-diazinane-2,4-dione
Traditional Namedihydrouracil
CAS Registry Number504-07-4
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 KeyOIVLITBTBDPEFK-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point279 - 281 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility25.9 g/LALOGPS
logP-1.3ALOGPS
logP-1.2ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.75 m³·mol⁻¹ChemAxon
Polarizability10.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9700000000-4adeeb2f4f5a1111afb72014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-5900000000-8af1b81502646fa5b4172014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0fdo-9750000000-d2aaeeba1cf962175f842014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-4adeeb2f4f5a1111afb72017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-5900000000-8af1b81502646fa5b4172017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fdo-9750000000-d2aaeeba1cf962175f842017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-2940000000-3430a0e2d1819021af1d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3900000000-79f2d90a419b7469cb612017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9100000000-55536f0571922b6c69fe2017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03fu-9400000000-5b9edda3479e7d0a0d282014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03k9-9800000000-da772cea603c785c1df42012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9100000000-94a5f543e8c6be7b32042012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0btc-9200000000-e9bf2ae82714a2a3a7372012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-5900000000-0fe83e63f6e5d13478942012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-6900000000-08aca1bc7f27b0e7cb082017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-5900000000-53ea361c86b4f9fa284b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9300000000-a8599c09cd21e2f843292017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-ad7f91d5265e53403dd62015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-9200000000-4b30a83fb454e5bbffb82015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ce54e3c860a95b0af4012015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9800000000-d705e188f6700a76ef722015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a26409d69a42597310042015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f00c4df547660023bee42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-b8f2cf36966bbbbb32852021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9500000000-44775319047d2eddad492021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-3cb7005ca8389854848e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-7900000000-9d78d5698ad7865d17892021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-997cffdd9ad85c8992252021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a88e812ae86e53f6c2d62021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Nucleus
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Kidney
  • Liver
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.31 (0.02-1.63) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.31 (0.02-1.63) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.32 ( 0.10-0.74) uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.1 +/- 1.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified700 +/- 199 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2168.16 +/- 127.94 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified2000 +/- 223 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2000 +/- 223 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2210 +/- 353 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2240 +/- 380 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2350 +/- 654 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
UrineDetected and Quantified0.79 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.8 (2.1-8.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified2.4 +/- 4.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.0 +/- 2.7 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified2.5-20 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified12.2 +/- 6.2 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified<3.4 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified81.5 (46.0-117.0) uMAdult (>18 years old)BothDihydropyrimidine dehydrogenase (DPD) deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified2.4 +/- 1.67 umol/mmol creatinineAdult (>18 years old)BothHypertension details
UrineDetected and Quantified627.0 umol/mmol creatinineInfant (0-1 year old)BothDihydropyrimidine dehydrogenase (DPD) deficiency details
UrineDetected and Quantified2.4 +/- 2.00 umol/mmol creatinineAdult (>18 years old)BothCerebral infarction details
UrineDetected and Quantified2.8 +/- 1.9 umol/mmol creatinineAdult (>18 years old)BothMalignancy details
UrineDetected and Quantified2.7 +/- 1.9 umol/mmol creatinineAdult (>18 years old)BothLiver dysfunction details
UrineDetected and Quantified2.5 +/- 2.00 umol/mmol creatinineAdult (>18 years old)BothNephropathy details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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
  1. 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 ]
  2. 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
  1. 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
  1. 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
  1. 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
DrugBank IDDB01849
Phenol Explorer Compound IDNot Available
FooDB IDFDB030556
KNApSAcK IDNot Available
Chemspider ID629
KEGG Compound IDC00429
BioCyc IDDI-H-URACIL
BiGG ID34956
Wikipedia LinkDihydrouracil
METLIN ID285
PubChem Compound649
PDB IDNot Available
ChEBI ID15901
Food Biomarker OntologyNot Available
VMH ID56DURA
MarkerDB IDMDB00000040
References
Synthesis ReferenceBhat, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. Tan BR, McLeod HL: Pharmacogenetic influences on treatment response and toxicity in colorectal cancer. Semin Oncol. 2005 Feb;32(1):113-9. [PubMed:15726513 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]

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 aciddetails
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 + NADPHdetails
Dihydrouracil + NADP → Uracil + NADPH + Hydrogen Iondetails