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Human Metabolome Database Version 3.5

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Showing metabocard for Deoxyuridine triphosphate (HMDB01191)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:04 -0700
HMDB ID HMDB01191
Secondary Accession Numbers None
Metabolite Identification
Common Name Deoxyuridine triphosphate
Description Deoxyuridine triphosphate is an intermediate in the metabolism of Pyrimidine. It is a substrate for Inosine triphosphate pyrophosphatase, Deoxyuridine 5'-triphosphate nucleotidohydrolase (mitochondrial), Uridine-cytidine kinase 1, Nucleoside diphosphate kinase 3, Nucleoside diphosphate kinase B, Nucleoside diphosphate kinase 6, Nucleoside diphosphate kinase (mitochondrial), Nucleoside diphosphate kinase homolog 5, Nucleoside diphosphate kinase A and Nucleoside diphosphate kinase 7.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2'-Deoxyuridine 5'-triphosphate
  2. 2'-Deoxyuridine-5'-triphosphorate
  3. 2'-Deoxyuridine-5'-triphosphoric acid
  4. 2'-Deoxyuridine-5'-triphosphoric acid = dUTP
  5. Deoxy-UTP
  6. Deoxyuridine triphosphate
  7. Deoxyuridine-5'-Triphosphate
  8. dUTP
Chemical Formula C9H15N2O14P3
Average Molecular Weight 468.1417
Monoisotopic Molecular Weight 467.973612734
IUPAC Name ({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name ({[(2R,3S,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number 1173-82-6
SMILES O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
InChI Identifier InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
InChI Key AHCYMLUZIRLXAA-SHYZEUOFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine Deoxyribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Deoxyribonucleotides(KEGG)
  • Pyrimidine Deoxyribonucleotides
  • deoxyuridine phosphate(ChEBI)
  • pyrimidine 2'-deoxyribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • Hydropyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct Parent Pyrimidine 2'-deoxyribonucleoside Triphosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pyrimidine metabolism
Application Not Available
Cellular locations
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
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
Water Solubility 8.63 g/L ALOGPS
LogP -0.12 ALOGPS
LogP -2.5 ChemAxon
LogS -1.73 ALOGPS
pKa (strongest acidic) 0.9 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 238.69 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 83.67 ChemAxon
Polarizability 34.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid Locations
  • Prostate Tissue
Tissue Location
  • Muscle
  • Epidermis
  • Prostate
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Prostate Tissue Detected and Quantified
Article_icon
0.5 (0.0-1.0) umol/g tissue Adult (>18 years old) Both Prostate cancer Estimated concentration
Associated Disorders and Diseases
Disease References
Prostate cancer
  • 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. Pubmed: 19212411 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022478
    KNApSAcK ID Not Available
    Chemspider ID 58580 Link_out
    KEGG Compound ID C00460 Link_out
    BioCyc ID DUTP Link_out
    BiGG ID 35037 Link_out
    Wikipedia Link Not Available
    NuGOwiki Link HMDB01191 Link_out
    Metagene Link HMDB01191 Link_out
    METLIN ID 6069 Link_out
    PubChem Compound 65070 Link_out
    PDB ID DUT Link_out
    ChEBI ID 17625 Link_out
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. Ge YF, Huang YF, Zhang GY, Wang XH, Xu JP: Studies on apoptosis of spermatogenic cells in normal fertile men treated with supraphysiological doses of testosterone undecanoate. Asian J Androl. 1999 Sep;1(3):155-8. Pubmed: 11250785 Link_out
    2. Gilhar A, Ullmann Y, Karry R, Shalaginov R, Assy B, Serafimovich S, Kalish RS: Ageing of human epidermis: the role of apoptosis, Fas and telomerase. Br J Dermatol. 2004 Jan;150(1):56-63. Pubmed: 14746617 Link_out
    3. Igarashi T, Brown CR, Byrum RA, Nishimura Y, Endo Y, Plishka RJ, Buckler C, Buckler-White A, Miller G, Hirsch VM, Martin MA: Rapid and irreversible CD4+ T-cell depletion induced by the highly pathogenic simian/human immunodeficiency virus SHIV(DH12R) is systemic and synchronous. J Virol. 2002 Jan;76(1):379-91. Pubmed: 11739702 Link_out
    4. Russell J, O'Donoghue JA, Finn R, Koziorowski J, Ruan S, Humm JL, Ling CC: Iodination of annexin V for imaging apoptosis. J Nucl Med. 2002 May;43(5):671-7. Pubmed: 11994533 Link_out
    5. Oosterhuis GJ, Mulder AB, Kalsbeek-Batenburg E, Lambalk CB, Schoemaker J, Vermes I: Measuring apoptosis in human spermatozoa: a biological assay for semen quality? Fertil Steril. 2000 Aug;74(2):245-50. Pubmed: 10927039 Link_out
    6. Lee AY, Youm YH, Kim NH, Yang H, Choi WI: Keratinocytes in the depigmented epidermis of vitiligo are more vulnerable to trauma (suction) than keratinocytes in the normally pigmented epidermis, resulting in their apoptosis. Br J Dermatol. 2004 Nov;151(5):995-1003. Pubmed: 15541077 Link_out
    7. Lamperti C, Naini AB, Lucchini V, Prelle A, Bresolin N, Moggio M, Sciacco M, Kaufmann P, DiMauro S: Muscle coenzyme Q10 level in statin-related myopathy. Arch Neurol. 2005 Nov;62(11):1709-12. Pubmed: 16286544 Link_out
    8. 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. Pubmed: 19212411 Link_out
    Enzymes
    Name: Uridine-cytidine kinase 1
    Reactions:
    • ATP + uridine = ADP + UMP [RN:R00964]
    Gene Name: UCK1
    Uniprot ID: Q9HA47 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nucleoside diphosphate kinase, mitochondrial
    Reactions:
    • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
    Gene Name: NME4
    Uniprot ID: O00746 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nucleoside diphosphate kinase A
    Reactions:
    • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
    Gene Name: NME1
    Uniprot ID: P15531 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nucleoside diphosphate kinase B
    Reactions:
    • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
    Gene Name: NME2
    Uniprot ID: P22392 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nucleoside diphosphate kinase 6
    Reactions:
    • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
    Gene Name: NME6
    Uniprot ID: O75414 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Inosine triphosphate pyrophosphatase
    Reactions:
    • a nucleoside triphosphate + H2O = a nucleotide + diphosphate [RN:R01532]
    Gene Name: ITPA
    Uniprot ID: Q9BY32 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Deoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrial
    Reactions:
    • dUTP + H2O = dUMP + diphosphate [RN:R02100]
    Gene Name: DUT
    Uniprot ID: P33316 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Uridine-cytidine kinase 2
    Reactions:
    • ATP + uridine = ADP + UMP [RN:R00964]
    Gene Name: UCK2
    Uniprot ID: Q9BZX2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Uridine-cytidine kinase-like 1
    Reactions:
    • ATP + uridine = ADP + UMP [RN:R00964]
    Gene Name: UCKL1
    Uniprot ID: Q9NWZ5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA