Record Information
Version1.0
Creation Date2016-09-30 22:39:43 UTC
Update Date2020-05-21 16:29:27 UTC
BMDB IDBMDB0001000
Secondary Accession Numbers
  • BMDB01000
Metabolite Identification
Common NamedUDP
DescriptiondUDP belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. dUDP is an extremely weak basic (essentially neutral) compound (based on its pKa). dUDP exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
ValueSource
2'-Deoxyuridine 5'-diphosphateChEBI
2'-Deoxyuridine 5'-diphosphoric acidGenerator
2'-Deoxyuridine-5'-diphosphateHMDB
Deoxyuridine-diphosphateHMDB
2'-Deoxyuridine 5'-(trihydrogen diphosphate)HMDB
2’-Deoxyuridine 5’-(trihydrogen diphosphate)HMDB
2’-Deoxyuridine 5’-diphosphateHMDB
Deoxyuridine 5'-diphosphateHMDB
Deoxyuridine 5’-diphosphateHMDB
Deoxyuridine diphosphateHMDB
dUDPHMDB
Chemical FormulaC9H14N2O11P2
Average Molecular Weight388.1618
Monoisotopic Molecular Weight388.007282324
IUPAC Name[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional NamedUDP
CAS Registry Number4208-67-7
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C9H14N2O11P2/c12-5-3-8(11-2-1-7(13)10-9(11)14)21-6(5)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
InChI KeyQHWZTVCCBMIIKE-SHYZEUOFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside diphosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside diphosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Lactam
  • Urea
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.99ALOGPS
logP-2.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area192.16 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.8 m³·mol⁻¹ChemAxon
Polarizability29.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001000
DrugBank IDDB03413
Phenol Explorer Compound IDNot Available
FooDB IDFDB022361
KNApSAcK IDNot Available
Chemspider ID128553
KEGG Compound IDC01346
BioCyc IDDUDP
BiGG ID37403
Wikipedia LinkNot Available
METLIN ID5931
PubChem Compound145729
PDB IDNot Available
ChEBI ID28850
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate (By similarity).
Gene Name:
NME7
Uniprot ID:
Q5E9Y9
Molecular weight:
42599.0
Reactions
Deoxyuridine triphosphate + ADP → dUDP + Adenosine triphosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
Q2TA32
Molecular weight:
39785.0
Reactions
dUMP + Adenosine triphosphate → dUDP + ADPdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
RRM2
Uniprot ID:
E1BI58
Molecular weight:
44821.0
Reactions
Uridine 5'-diphosphate + Thioredoxin disulfide + Water → dUDP + Thioredoxindetails