ECMDB: Uridine diphosphate glucuronic acid (ECMDB04166) (M2MDB000646)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (4)XML

Proteins (9)

Record Information

Version

2.0

Creation Date

2012-05-31 14:07:02 -0600

Update Date

2015-06-03 15:54:49 -0600

Secondary Accession Numbers

ECMDB04166

Identification

Name:

Uridine diphosphate glucuronic acid

Description

Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. It is made from UDP-glucose by UDP-glucose 6-dehydrogenase (EC 1.1.1.22) using NAD+ as a cofactor. It is the source of the glucuronosyl group in glucuronosyltransferase reactions. (Wikipedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(UDP-GlcA)1
A-D-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
a-D-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
A-D-Glucopyranuronate ester with uridine 5'-pyrophosphate
A-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
a-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
A-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphate
a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
a-delta-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
a-delta-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
a-delta-Glucopyranuronate ester with uridine 5'-pyrophosphate
a-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
a-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
a-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
a-δ-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
a-δ-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
a-δ-Glucopyranuronate ester with uridine 5'-pyrophosphate
a-δ-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
a-δ-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
a-δ-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
Alpha-D-Glucopyranuronate 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
Alpha-D-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
Alpha-delta-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
Alpha-delta-Glucopyranuronate 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
Alpha-delta-Glucopyranuronate ester with uridine 5'-pyrophosphate
Alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
Alpha-delta-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)
alpha-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
Alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphate
alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid
GDP-GlcA
Glucopyranuronate 1-ester with uridine 5'-pyrophosphate
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphoric acid
UDP Glucuronate
UDP Glucuronic acid
UDP-a-D-Glucuronate
UDP-a-D-Glucuronic acid
UDP-a-delta-Glucuronate
UDP-a-delta-Glucuronic acid
UDP-a-δ-Glucuronate
UDP-a-δ-Glucuronic acid
UDP-alpha-D-Glucuronate
UDP-alpha-D-Glucuronic acid
UDP-alpha-delta-Glucuronate
UDP-alpha-delta-Glucuronic acid
UDP-D-Glucuronate
UDP-D-Glucuronic acid
UDP-delta-Glucuronate
UDP-delta-Glucuronic acid
UDP-GlcUA
UDP-Glucuronate
UDP-Glucuronic acid
UDP-L-Iduronate
UDP-L-Iduronic acid
UDP-α-D-Glucuronate
UDP-α-D-Glucuronic acid
UDP-α-δ-Glucuronate
UDP-α-δ-Glucuronic acid
UDP-δ-Glucuronate
UDP-δ-Glucuronic acid
UDPGA
UDPglucuronate
UDPglucuronic acid
UGA
Uridine 5'-diphospho-a-D-glucuronate
Uridine 5'-diphospho-a-D-glucuronic acid
Uridine 5'-diphospho-a-delta-glucuronate
Uridine 5'-diphospho-a-delta-glucuronic acid
Uridine 5'-diphospho-a-δ-glucuronate
Uridine 5'-diphospho-a-δ-glucuronic acid
Uridine 5'-diphospho-alpha-delta-glucuronate
Uridine 5'-diphospho-alpha-delta-glucuronic acid
Uridine 5'-diphospho-glucuronate
Uridine 5'-diphospho-glucuronic acid
Uridine 5'-diphospho-α-δ-glucuronate
Uridine 5'-diphospho-α-δ-glucuronic acid
Uridine 5'-diphosphoglucuronate
Uridine 5'-diphosphoglucuronic acid
Uridine 5'-[3-(D-glucopyranosyloxyuronate) dihydrogen diphosphate]
Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]
Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphoric acid]
Uridine diphosphate glucuronate
Uridine diphosphate glucuronic acid
Uridine diphosphate-glucuronate
Uridine diphosphate-glucuronic acid
Uridine diphospho-D-glucuronate
Uridine diphospho-D-glucuronic acid
Uridine diphospho-delta-glucuronate
Uridine diphospho-delta-glucuronic acid
Uridine diphospho-δ-glucuronate
Uridine diphospho-δ-glucuronic acid
Uridine diphosphoglucuronate
Uridine diphosphoglucuronic acid
Uridine diphosphoric acid glucuronic acid
Uridine diphosphoric acid-glucuronic acid
Uridine pyrophosphoglucuronate
Uridine pyrophosphoglucuronic acid
Uridinediphosphoglucuronate
Uridinediphosphoglucuronic acid
α-D-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
α-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
α-δ-Glucopyranuronate 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)
α-δ-Glucopyranuronate 1-p'-ester with uridine 5'-(trihydrogen diphosphate)
α-δ-Glucopyranuronate ester with uridine 5'-pyrophosphate
α-δ-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphoric acid)
α-δ-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphoric acid)
α-δ-Glucopyranuronic acid ester with uridine 5'-pyrophosphoric acid

Chemical Formula:

C₁₅H₂₂N₂O₁₈P₂

Weight:

Average: 580.2853
Monoisotopic: 580.034284934

InChI Key:

HDYANYHVCAPMJV-LXQIFKJMSA-N

InChI:

InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1

CAS number:

2616-64-0

IUPAC Name:

(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional IUPAC Name:

udp-α-D-glucuronic acid

SMILES:

O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diol (CHEBI:71176 )
butan-4-olide (CHEBI:71176 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	18.1 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-4.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	308.61 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.32 m³·mol⁻¹	ChemAxon
Polarizability	45.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Starch and sucrose metabolism

PW000941

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Ascorbate and aldarate metabolism ec00053
Pentose and glucuronate interconversions ec00040
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

colanic acid building blocks biosynthesis COLANSYN-PWY
polymyxin resistance PWY0-1338

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
83± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776
566± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
375± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
188± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
296± 12 uM	BL21 DE3	Luria-Bertani (LB) media	Stationary phase cultures (overnight culture)	Shake flask	37 oC	Experimentally Determined Download Details

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-3322930000-0ce18416678ea80bec67	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-004r-4862914000-b91973e084ab99d92364	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucuronic acid,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0135690000-0ff1e6a4900ecdc6a915	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-0000090000-1cdeb28950f03fda28ea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0r29-5934300000-e5fcfe66852c383b82d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-bc00d530c5ce60dfe672	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3922200000-353e174f91c8b182064c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-d434fad6ebdd7797c473	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-b27e8f43f987aadd35fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4900000000-6c8ee9c73e164f9ccf76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0imu-4601190000-7a0e82462b874f18b2c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-9817020000-a72141b1bee762a83bc3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-4901000000-5d52b1b8f03063646a7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0001090000-c773521e9e340d5e6564	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055e-9424840000-deea5ee6888efff36f31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5a-3936510000-b41af0ea55c95b9da1e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1700490000-7f9159b24d34e9358740	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4921760000-cd1fe2a62f343b8eb5ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0209-6940100000-aa916ad8a0ed15e6eb2a	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Alkharfy KM, Frye RF: High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. J Chromatogr B Biomed Sci Appl. 2001 Apr 5;753(2):303-8. Pubmed: 11334344
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Cappiello M, Giuliani L, Pacifici GM: Distribution of UDP-glucuronosyltransferase and its endogenous substrate uridine 5'-diphosphoglucuronic acid in human tissues. Eur J Clin Pharmacol. 1991;41(4):345-50. Pubmed: 1804651
Cappiello M, Giuliani L, Rane A, Pacifici GM: Uridine 5'-diphosphoglucuronic acid (UDPGLcUA) in the human fetal liver, kidney and placenta. Eur J Drug Metab Pharmacokinet. 2000 Jul-Dec;25(3-4):161-3. Pubmed: 11420884
Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990
Fondeur-Gelinotte M, Lattard V, Oriol R, Mollicone R, Jacquinet JC, Mulliert G, Gulberti S, Netter P, Magdalou J, Ouzzine M, Fournel-Gigleux S: Phylogenetic and mutational analyses reveal key residues for UDP-glucuronic acid binding and activity of beta1,3-glucuronosyltransferase I (GlcAT-I). Protein Sci. 2006 Jul;15(7):1667-78. Pubmed: 16815917
Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. Pubmed: 14977865
Hagenauer B, Salamon A, Thalhammer T, Kunert O, Haslinger E, Klingler P, Senderowicz AM, Sausville EA, Jager W: In vitro glucuronidation of the cyclin-dependent kinase inhibitor flavopiridol by rat and human liver microsomes: involvement of UDP-glucuronosyltransferases 1A1 and 1A9. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):407-14. Pubmed: 11259324
Huskey SW, Doss GA, Miller RR, Schoen WR, Chiu SH: N-glucuronidation reactions. II. Relative N-glucuronidation reactivity of methylbiphenyl tetrazole, methylbiphenyl triazole, and methylbiphenyl imidazole in rat, monkey, and human hepatic microsomes. Drug Metab Dispos. 1994 Jul-Aug;22(4):651-8. Pubmed: 7956743
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Quintus J, Kovar KA, Link P, Hamacher H: Urinary excretion of arbutin metabolites after oral administration of bearberry leaf extracts. Planta Med. 2005 Feb;71(2):147-52. Pubmed: 15729623
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Simon, Ethan S.; Grabowski, Sven; Whitesides, George M. Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose. Journal

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17200
HMDB ID	HMDB00935
Pubchem Compound ID	17473
Kegg ID	C00167
ChemSpider ID	16522
Wikipedia	Uridine diphosphate glucuronic acid
BioCyc ID	UDP-GLUCURONATE
EcoCyc ID	UDP-GLUCURONATE
Ligand Expo	UGA

Enzymes

Protein Details

1. Protein ushA

General function:: Involved in hydrolase activity
Specific function:: Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:: ushA
Uniprot ID:: P07024
Molecular weight:: 60824

Reactions

UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.

Protein Details

2. UDP-glucose 6-dehydrogenase

General function:: Involved in oxidation-reduction process
Specific function:: UDP-glucose + 2 NAD(+) + H(2)O = UDP- glucuronate + 2 NADH
Gene Name:: ugd
Uniprot ID:: P76373
Molecular weight:: 43656

Reactions

UDP-glucose + 2 NAD(+) + H(2)O = UDP-glucuronate + 2 NADH.

Protein Details

3. Bifunctional polymyxin resistance protein ArnA

General function:: Involved in hydroxymethyl-, formyl- and related transferase activity
Specific function:: Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto- arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4- amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido- arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:: arnA
Uniprot ID:: P77398
Molecular weight:: 74288

Reactions

UDP-alpha-D-glucuronate + NAD(+) = UDP-beta-L-threo-pentapyranos-4-ulose + CO(2) + NADH.
10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinose.

Transporters

Protein Details

1. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

2. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

3. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

4. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Uridine diphosphate glucuronic acid (ECMDB04166) (M2MDB000646)

Structure for #<Compound:0xae7550cc>

Enzymes

Reactions

Reactions

Reactions

Transporters