| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:15 -0700 |
| HMDB ID |
HMDB00295 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Uridine 5'-diphosphate |
| Description |
Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596 ). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 5'-UDP
- UDP
- Uridine 5'-diphosphate
- Uridine 5'-pyrophosphate
- Uridine 5'-pyrophosphorate
- Uridine 5'-pyrophosphoric acid
- Uridine diphosphate
- Uridine pyrophosphate
|
| Chemical Formula |
C9H14N2O12P2 |
| Average Molecular Weight |
404.1612 |
| Monoisotopic Molecular Weight |
404.002196946 |
| IUPAC Name |
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
| Traditional IUPAC Name |
{[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid |
| CAS Registry Number |
58-98-0 |
| SMILES |
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O |
| InChI Identifier |
InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 |
| InChI Key |
XCCTYIAWTASOJW-XVFCMESISA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Pyrimidine Nucleotides |
| Sub Class |
Pyrimidine Ribonucleotides |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- Ribonucleotides(KEGG)
- pyrimidine ribonucleoside 5'-diphosphate(ChEBI)
- uridine 5'-phosphate(ChEBI)
|
| Substituents |
- 1,2 Diol
- Glycosyl Compound
- Hydropyrimidine
- Monosaccharide Phosphate
- N Glycosyl Compound
- Organic Hypophosphite
- Organic Phosphite
- Organic Pyrophosphate
- Oxolane
- Pentose Monosaccharide
- Phosphoric Acid Ester
- Pyrimidine
- Pyrimidone
- Saccharide
- Secondary Alcohol
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| Direct Parent |
Pyrimidine Ribonucleoside Diphosphates |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
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| 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 |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
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| Biofluid Locations |
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| Tissue Location |
- Placenta
- Thyroid Gland
- Prostate
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
41.0 +/- 12.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
DB03435  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB007509 |
| KNApSAcK ID |
C00007313  |
| Chemspider ID |
5809  |
| KEGG Compound ID |
C00015  |
| BioCyc ID |
UDP  |
| BiGG ID |
33518  |
| Wikipedia Link |
UDP  |
| NuGOwiki Link |
HMDB00295  |
| Metagene Link |
HMDB00295  |
| METLIN ID |
Not Available |
| PubChem Compound |
6031  |
| PDB ID |
UDP  |
| ChEBI ID |
17659  |
| References |
| Synthesis Reference |
Zeng, Bin; Rao, Linfan; Li, Gaowo. Method for manufacturing uridine diphosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 14pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Brouwer A, Morse DC, Lans MC, Schuur AG, Murk AJ, Klasson-Wehler E, Bergman A, Visser TJ: Interactions of persistent environmental organohalogens with the thyroid hormone system: mechanisms and possible consequences for animal and human health. Toxicol Ind Health. 1998 Jan-Apr;14(1-2):59-84.
Pubmed: 9460170
- Kamisako T, Kobayashi Y, Takeuchi K, Ishihara T, Higuchi K, Tanaka Y, Gabazza EC, Adachi Y: Recent advances in bilirubin metabolism research: the molecular mechanism of hepatocyte bilirubin transport and its clinical relevance. J Gastroenterol. 2000;35(9):659-64.
Pubmed: 11023036
- Syme MR, Paxton JW, Keelan JA: Drug transfer and metabolism by the human placenta. Clin Pharmacokinet. 2004;43(8):487-514.
Pubmed: 15170365
- Collier AC, Tingle MD, Paxton JW, Mitchell MD, Keelan JA: Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. Hum Reprod. 2002 Oct;17(10):2564-72.
Pubmed: 12351530
- 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
|
| Enzymes |
| Name: |
UMP-CMP kinase
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| Reactions: |
- ATP + (d)CMP = ADP + (d)CDP [RN:R00512 R01665]
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| Gene Name: |
CMPK1 |
| Uniprot ID: |
P30085  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-1,4 N-acetylgalactosaminyltransferase 1
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| Reactions: |
- UDP-N-acetyl-D-galactosamine + 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D- galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide = UDP + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-[N- acetyl-alpha-neuraminosyl-(2->3)]-O-beta-D-galactopyranosyl-(1->4)- beta-D-glucopyranosyl]-ceramide [RN:R04584 R05939]
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| Gene Name: |
B4GALNT1 |
| Uniprot ID: |
Q00973  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lactosylceramide 4-alpha-galactosyltransferase
|
| Reactions: |
- UDP-galactose + beta-D-galactosyl-(1->4)-D-glucosyl-(11)-ceramide = UDP + alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-D-glucosyl-(11)- ceramide [RN:R03486 R05960]
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| Gene Name: |
A4GALT |
| Uniprot ID: |
Q9NPC4  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
UDP-GalNAc:beta-1,3-N-acetylgalactosaminyltransferase 1
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| Reactions: |
- UDP-N-acetyl-D-galactosamine + alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl- (11)-ceramide = UDP + N-acetyl-beta-D-galactosaminyl-(1->3)-alpha-D-galactosyl-(1->4)- beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide [RN:R05631 R05962]
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| Gene Name: |
B3GALNT1 |
| Uniprot ID: |
O75752  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycogenin-1
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| Reactions: |
- UDP-alpha-D-glucose + glycogenin = UDP + alpha-D-glucosylglycogenin [RN:R03681]
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| Gene Name: |
GYG1 |
| Uniprot ID: |
P46976  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycogenin-2
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| Reactions: |
- UDP-alpha-D-glucose + glycogenin = UDP + alpha-D-glucosylglycogenin [RN:R03681]
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| Gene Name: |
GYG2 |
| Uniprot ID: |
O15488  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Histo-blood group ABO system transferase
|
| Reactions: |
- UDP-N-acetyl-D-galactosamine + glycoprotein-alpha-L-fucosyl-(1->2)-D-galactose = UDP + glycoprotein-N-acetyl-alpha-D-galactosaminyl-(1->3)-[alpha-L- fucosyl-(1->2)]-D-galactose [RN:R04423]
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| Gene Name: |
ABO |
| Uniprot ID: |
P16442  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Chondroitin sulfate synthase 3
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
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| Gene Name: |
CHSY3 |
| Uniprot ID: |
Q70JA7  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Chondroitin sulfate synthase 2
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
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| Gene Name: |
CHPF |
| Uniprot ID: |
Q8IZ52  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Chondroitin sulfate synthase 1
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
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| Gene Name: |
CHSY1 |
| Uniprot ID: |
Q86X52  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Exostosin-1
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-alpha-D-glucosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->4)-N-acetyl-alpha-D-glucosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07335]
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| Gene Name: |
EXT1 |
| Uniprot ID: |
Q16394  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hyaluronan synthase 1
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| Reactions: |
- (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
- (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
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| Gene Name: |
HAS1 |
| Uniprot ID: |
Q92839  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Exostosin-like 3
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| Reactions: |
- UDP-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-beta-D-galactosyl-(1->3)-beta-D- galactosyl-(1->4)-beta-D-xylosyl-proteoglycan = UDP + alpha-N-acetyl-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- beta-D-galactosyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-xylosyl- proteoglycan [RN:R05930]
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| Gene Name: |
EXTL3 |
| Uniprot ID: |
O43909  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Exostosin-2
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-alpha-D-glucosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->4)-N-acetyl-alpha-D-glucosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07335]
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| Gene Name: |
EXT2 |
| Uniprot ID: |
Q93063  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Exostosin-like 1
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| Reactions: |
- UDP-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->4)-N-acetyl-alpha-D-glucosaminyl- proteoglycan = UDP + N-acetyl-alpha-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->4)-N- acetyl-alpha-D-glucosaminyl-proteoglycan [RN:R07334]
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| Gene Name: |
EXTL1 |
| Uniprot ID: |
Q92935  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hyaluronan synthase 3
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| Reactions: |
- (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
- (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
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| Gene Name: |
HAS3 |
| Uniprot ID: |
O00219  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hyaluronan synthase 2
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| Reactions: |
- (1) UDP-alpha-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)- [nascent hyaluronan] = UDP + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)-N- acetyl-beta-D-glucosaminyl-(1->4)-[nascent hyaluronan] [RN:R05327 R06068]
- (2) UDP-alpha-D-glucuronate + N-acetyl-beta-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- [nascent hyaluronan] = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->4)-beta- D-glucuronosyl-(1->3)-[nascent hyaluronan]
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| Gene Name: |
HAS2 |
| Uniprot ID: |
Q92819  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Chondroitin sulfate glucuronyltransferase
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| Reactions: |
- UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-(1->4)-beta-D-glucuronosyl- proteoglycan = UDP + beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)- beta-D-glucuronosyl-proteoglycan [RN:R07336]
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| Gene Name: |
CHPF2 |
| Uniprot ID: |
Q9P2E5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Exostosin-like 2
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| Reactions: |
- UDP-N-acetyl-D-glucosamine + beta-D-glucuronosyl-(1->3)-beta-D-galactosyl-(1->3)-beta-D- galactosyl-(1->4)-beta-D-xylosyl-proteoglycan = UDP + alpha-N-acetyl-D-glucosaminyl-(1->4)-beta-D-glucuronosyl-(1->3)- beta-D-galactosyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-xylosyl- proteoglycan [RN:R05930]
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| Gene Name: |
EXTL2 |
| Uniprot ID: |
Q9UBQ6  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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