We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Metabolome Database



Showing metabocard for Dihydrouracil (BMDB00076)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-12 13:10:52
Accession Number BMDB00076
Common Name Dihydrouracil
Description An intermediate breakdown product of uracil. Dihydropyrimidine dehydrogenase catalyzes the reduction of uracil to 5, 6-dihydrouracil then dihydropyrimidinase hydrolyzes 5, 6-dihydrouracil to N-carbamyl-b-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-b-alanine to beta-alanine. Patients with dihydropyrimidinase deficiency (DPYS; also called 5, 6-dihydropyrimidine amidohydrolase, or DHP; EC 3.5.2.2) exhibit highly increased concentrations of 5, 6-dihydrouracil in urine. The direct measurement of the activity of DHP in patients had been hampered by the fact that the enzyme is expressed almost exclusively in liver tissue. Various neurological abnormalities have been described in this group of patients. (OMIM 222748)
Synonyms
  1. 5,6-Dihydro-2,4(1H,3H)-pyrimidinedione
  2. 5,6-Dihydro-2,4-dihydroxypyrimidine
  3. 5,6-Dihydrouracil
  4. Dihydro-2,4(1H,3H)-pyrimidinedione
  5. Dihydro-pyrimidine-2,4-dione
  6. Dihydrouracil
  7. Dihydrouracile
  8. Hydrouracil
Chemical IUPAC Name 1,3-diazinane-2,4-dione
Chemical Formula C4H6N2O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Pyrimidines and Derivatives
Sub Class
  • Hydroxy pyrimidines
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid imide, N-unsubstituted; urea; heterocyclic compound
Biofunction
  • Component of beta-Alanine metabolism; Component of Pantothenate and CoA biosynthesis; Component of Pyrimidine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 114.103
Monoisotopic Molecular Weight 114.042931
Isomeric SMILES O=C1CCNC(=O)N1
Canonical SMILES O=C1CCNC(=O)N1
KEGG Compound ID C00429 Link Image
BioCyc ID DI-H-URACIL Link Image
BiGG ID 34956 Link Image
Wikipedia Link Not Available
METLIN ID 285 Link Image
PubChem Compound 649 Link Image
PubChem Substance 10391739 Link Image
ChEBI ID 15901 Link Image
CAS Registry Number 504-07-4
InChI Identifier InChI=1/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
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.
Melting Point (Experimental) 279-281 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 25.9 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.28 [Predicted by ALOGPS]; -1.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Nucleus
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Fibroblasts
Kidney
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Beta Alanine Metabolism
  • Pantothenate and CoA Biosynthesis
  • Pyrimidine Metabolism
HMDB Pathways
Name Beta Alanine Metabolism
Image Show Link Image
Name Pantothenate and CoA Biosynthesis
Image Show Link Image
Name Pyrimidine Metabolism
Image Show Link Image
KEGG Pathways
Name Beta Alanine Metabolism
Image Show Link Image
Name Pantothenate and CoA Biosynthesis
Image Show Link Image
Name Pyrimidine Metabolism
Image Show Link Image
SimCell Pathways
Name Beta Alanine Metabolism
Image Show Link Image
Graph
SBML
Name Pyrimidine Metabolism
Image Show Link Image
Graph
SBML
General References Not Available
Metabolic Enzymes
  1. Dihydropyrimidine dehydrogenase [NADP+]
Enzyme 1 [top]
Enzyme 1 ID 689
Enzyme 1 Name Dihydropyrimidine dehydrogenase [NADP+]
Enzyme 1 Synonyms
  1. DHPDHase
  2. DPD
  3. Dihydrouracil dehydrogenase
  4. Dihydrothymine dehydrogenase
Enzyme 1 Gene Name DPYD
Enzyme 1 Protein Sequence >Dihydropyrimidine dehydrogenase [NADP+]
MAPVLSKDVADIESILALNPRTQSRATLRSTLAKKLDKKHWKRNPDKNCFNCEKLENNFD
DIKHTTLGERGALREAMRCLKCADAPCQKSCPTNLDIKSFITSISNKNYYGAAKMIFSDN
PLGLTCGMVCPTSDLCVGGCNLYATEEGPINIGGLQQYATEVFKAMNIPQIRNPSLPPPE
KMPEAYSAKIALLGAGPASISCASFLARLGYNDITIFEKQEYVGGISTSEIPQFRLPYDV
VNFEIELMKDLGVKIICGKSLSVNDITLSTLKEEGYKAAFIGIGLPEPKKDHIFQGLTQD
QGFYTSKDFLPLVAKSSKAGMCACHSPLLSIRGTVIVLGAGDTAFDCATSALRCGARRVF
IVFRKGFVNIRAVPEEVELAREEKCEFLPFLSPRKVIVKGGRIVAMQFVRTEQDETGKWN
EDGDQIACLKADVVISAFGSVLSDPKVKEALSPIKFNRWDLPEVDPETMQTSEPWVFAGG
DVVGIANTTVEAVNDGKQASWYIHRYIQSQYGASVSAKPELPLFYTPIDLVDISVEMAAL
KFTNPFGLASATPTTSSSMIRRAFEAGWAFALTKTFSLDKDIVTNVSPRIIRGTTSGPMY
GPGQSSFLNIELISEKTAAYWCQSVTELKADFPDNIVIASIMCSYNRNDWMELSRKAEAS
GADALELNLSCPHGMGERGMGLACGQDPELVRNICRWVRQAVRIPFFAKLTPNVTDIVSI
ARAAKEGGANGVTATNTVSGLMGLKADGTPWPAVGREKRTTYGGVSGTAIRPIALRAVTT
IARALPEFPILATGGIDSAESGLQFLHGGASVLQVCSAIQNQDFTIIQDYCTGLKALLYL
KSIEELQDWDGQSPATKSHQKGKPVPCIAELVGKKLPSFGPYLEKCKKIIAEEKLRLKKE
NVTVLPLERNHFIPKKPIPSVKDVIGKALQYLGTYGELNNTEQVVAVIDEEMCINCGKCY
MTCNDSGYQAIQFDPETHLPTVTDTCTGCTLCLSVCPIIDCIKMVSRTTPYEPKRGLPLA
VNPVS
Enzyme 1 Number of Residues 1025
Enzyme 1 Molecular Weight 111695.6
Enzyme 1 Theoretical pI 7.32
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine
Enzyme 1 Pathways
  • Amino-acid biosynthesis
  • beta-alanine biosynthesis
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 677951 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q28007 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name DPYD_BOVIN Link Image
Enzyme 1 PDB ID 1GTE Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >3078 bp
ATGGCCCCTGTGCTAAGCAAGGACGTGGCGGATATCGAGAGTATCCTGGCTTTAAATCCT
CGAACACAGTCTCGTGCAACTCTGCGTTCCACTTTGGCCAAGAAATTAGACAAGAAACAT
TGGAAAAGAAATCCTGATAAGAACTGCTTTAATTGCGAGAAGCTGGAGAATAATTTTGAT
GACATCAAGCACACGACTCTTGGTGAGCGAGGAGCTCTCCGAGAAGCAATGAGATGCCTG
AAATGTGCAGATGCCCCCTGTCAGAAGAGCTGTCCAACAAATCTAGATATCAAATCGTTC
ATCACAAGTATCTCAAACAAGAACTATTATGGAGCTGCTAAGATGATATTTTCTGACAAC
CCACTTGGTCTGACCTGTGGAATGGTATGCCCCACCTCTGATCTTTGTGTAGGTGGATGT
AATTTGTATGCCACTGAAGAGGGACCAATTAATATTGGTGGATTGCAGCAATATGCTACT
GAGGTATTCAAAGCAATGAATATCCCACAAATCAGGAATCCTTCTCTGCCTCCCCCAGAA
AAAATGCCTGAAGCCTATTCTGCAAAGATTGCTCTTTTGGGTGCTGGGCCTGCAAGTATA
AGTTGTGCTTCGTTCTTGGCTCGATTAGGCTACAATGACATCACTATATTTGAAAAACAA
GAATACGTTGGTGGTATAAGTACTTCTGAAATCCCTCAGTTCCGGCTGCCATATGATGTA
GTAAATTTTGAGATTGAGCTTATGAAGGACCTTGGTGTAAAGATAATTTGTGGTAAAAGC
CTTTCAGTGAATGACATTACTCTTAGTACTTTGAAAGAAGAAGGGTACAAAGCTGCTTTC
ATTGGGATAGGTTTGCCAGAACCCAAGAAGGATCACATCTTCCAAGGCCTGACACAGGAC
CAGGGGTTTTACACTTCCAAAGACTTTCTGCCTCTTGTAGCCAAAAGCAGTAAAGCAGGA
ATGTGCGCCTGTCACTCTCCATTGCTGTCGATACGGGGAACCGTGATTGTACTCGGAGCT
GGAGACACAGCTTTCGACTGTGCAACATCCGCTTTACGTTGTGGAGCCCGCCGAGTGTTC
ATCGTCTTCAGAAAAGGCTTTGTTAATATAAGAGCTGTCCCTGAGGAGGTGGAGCTTGCT
AGAGAAGAAAAATGTGAATTTTTGCCTTTCTTGTCTCCACGGAAGGTTATAGTAAAAGGT
GGGAGAATTGTTGCCATGCAATTTGTTCGGACAGAGCAAGATGAAACTGGAAAATGGAAT
GAAGATGGAGATCAGATAGCCTGTCTGAAAGCCGATGTGGTCATCAGTGCCTTTGGCTCA
GTTCTGAGTGATCCTAAAGTAAAAGAAGCCTTGAGCCCTATAAAATTTAACAGATGGGAT
CTCCCAGAAGTAGATCCAGAAACTATGCAAACCAGTGAGCCATGGGTGTTTGCAGGTGGT
GATGTGGTTGGTATAGCCAACACTACAGTGGAAGCCGTGAATGATGGAAAGCAAGCCTCT
TGGTACATTCACAGATATATACAGTCACAATATGGAGCTTCAGTTTCTGCTAAGCCCGAA
CTCCCCCTGTTTTATACTCCCATTGATCTGGTGGACATTAGTGTGGAAATGGCTGCATTG
AAGTTTACAAATCCTTTTGGTCTTGCCAGTGCAACTCCAACTACCAGTTCGTCAATGATT
CGAAGAGCTTTTGAAGCTGGATGGGCCTTTGCTCTGACCAAAACTTTCTCTCTTGATAAG
GATATAGTGACAAATGTTTCACCCAGAATCATCCGGGGGACCACCTCTGGCCCCATGTAT
GGCCCTGGACAAAGCTCTTTCCTGAATATTGAGCTCATCAGTGAAAAAACGGCTGCATAT
TGGTGTCAAAGTGTCACTGAACTAAAAGCCGACTTTCCAGACAATATTGTGATTGCTAGC
ATCATGTGCAGTTACAACAGAAATGACTGGATGGAACTCTCCAGAAAGGCTGAGGCTTCT
GGAGCAGACGCCCTGGAGTTAAATTTATCGTGTCCGCATGGCATGGGAGAAAGAGGAATG
GGTCTGGCTTGTGGACAGGATCCAGAGCTGGTGCGGAACATCTGTCGCTGGGTTAGGCAA
GCTGTTCGGATTCCTTTTTTTGCCAAGTTGACCCCAAATGTCACTGATATTGTAAGCATA
GCCAGAGCTGCAAAGGAAGGTGGGGCAAATGGTGTTACAGCTACCAACACTGTCTCAGGT
CTCATGGGATTAAAAGCTGATGGCACACCCTGGCCAGCAGTGGGCCGTGAGAAGCGGACT
ACATACGGCGGAGTGTCCGGCACAGCCATCAGACCTATTGCTTTGAGAGCTGTGACCACC
ATTGCTCGTGCTTTGCCTGAATTTCCCATTTTGGCCACTGGTGGAATTGACTCAGCTGAA
AGTGGTCTTCAGTTTCTCCACGGTGGTGCTTCGGTGCTCCAGGTATGCAGTGCTATTCAA
AATCAGGATTTCACTATCATCCAAGACTACTGCACTGGCCTCAAAGCCTTGCTTTATCTG
AAAAGCATTGAAGAACTACAGGACTGGGATGGGCAGAGTCCAGCCACGAAGAGTCACCAG
AAAGGGAAACCAGTCCCTTGTATTGCTGAACTTGTGGGAAAGAAACTGCCAAGCTTTGGA
CCTTATCTTGAGAAGTGCAAGAAAATCATAGCAGAGGAAAAGTTGAGACTGAAAAAAGAA
AATGTGACCGTTCTACCACTTGAAAGAAACCATTTTATCCCAAAAAAACCTATTCCTTCT
GTTAAGGATGTGATTGGAAAAGCTCTGCAGTACCTTGGAACATATGGTGAACTGAACAAC
ACAGAGCAGGTTGTGGCTGTGATCGATGAAGAGATGTGTATCAACTGTGGCAAATGCTAC
ATGACCTGTAATGACTCTGGCTACCAGGCTATCCAGTTTGATCCTGAAACCCACCTGCCC
ACCGTTACTGACACTTGTACAGGCTGTACCCTGTGTCTCTCCGTCTGCCCTATTATCGAC
TGCATCAAAATGGTTTCCAGGACAACACCTTATGAACCAAAGAGAGGCTTGCCCTTGGCT
GTGAATCCTGTGTCTTAA
Enzyme 1 GenBank Gene ID U20981 Link Image
Enzyme 1 GeneCard ID DPYD Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 1p22
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available