Bovine Metabolome Database: Showing metabocard for Uridine diphosphate glucuronic acid (BMDB0000935)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:49 UTC

Update Date

2020-05-21 16:26:58 UTC

BMDB ID

BMDB0000935

Secondary Accession Numbers

BMDB00935

Metabolite Identification

Common Name

Uridine diphosphate glucuronic acid

Description

Uridine diphosphate glucuronic acid, also known as udpglucuronate or UDP-a-D-glucuronic acid, 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. Uridine diphosphate glucuronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucuronic acid exists in all living species, ranging from bacteria to humans. Within cattle, uridine diphosphate glucuronic acid participates in a number of enzymatic reactions. In particular, 2-methoxyestrone and uridine diphosphate glucuronic acid can be converted into 2-methoxyestrone 3-glucuronide and uridine 5'-diphosphate through the action of the enzyme UDP-glucuronosyltransferase 1-1. In addition, estrone and uridine diphosphate glucuronic acid can be converted into estrone glucuronide and uridine 5'-diphosphate; which is mediated by the enzyme UDP-glucuronosyltransferase 1-1. In cattle, uridine diphosphate glucuronic acid is involved in the metabolic pathway called the estrone metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
UDP-alpha-D-Glucuronate	ChEBI
UDP-D-Glucuronate	ChEBI
UDP-Glucuronate	ChEBI
UDPglucuronate	ChEBI
URIDINE-5'-diphosphATE-glucuronIC ACID	ChEBI
UDP-a-D-Glucuronate	Generator
UDP-a-D-Glucuronic acid	Generator
UDP-alpha-D-Glucuronic acid	Generator
UDP-Α-D-glucuronate	Generator
UDP-Α-D-glucuronic acid	Generator
UDP-D-Glucuronic acid	Generator
UDP-Glucuronic acid	Generator
UDPglucuronic acid	Generator
URIDINE-5'-diphosphate-glucuronate	Generator
URIDINE-5'-diphosphoric acid-glucuronic acid	Generator
Uridine diphosphate glucuronate	Generator
Uridine diphosphoric acid glucuronic acid	Generator
a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)	HMDB
a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphate	HMDB
alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)	HMDB
alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)	HMDB
alpha-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)	HMDB
alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphate	HMDB
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate	HMDB
UDP Glucuronate	HMDB
UDP Glucuronic acid	HMDB
UDP-alpha-delta-Glucuronate	HMDB
UDP-delta-Glucuronate	HMDB
UDP-delta-Glucuronic acid	HMDB
UDP-GlcUA	HMDB
UDPGA	HMDB
UGA	HMDB
Uridine 5'-diphospho-a-D-glucuronate	HMDB
Uridine 5'-diphospho-a-D-glucuronic acid	HMDB
Uridine 5'-diphospho-alpha-delta-glucuronate	HMDB
Uridine 5'-diphospho-alpha-delta-glucuronic acid	HMDB
Uridine 5'-diphospho-glucuronic acid	HMDB
Uridine 5'-diphosphoglucuronate	HMDB
Uridine 5'-diphosphoglucuronic acid	HMDB
Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]	HMDB
Uridine diphosphate-glucuronate	HMDB
Uridine diphospho-D-glucuronate	HMDB
Uridine diphospho-D-glucuronic acid	HMDB
Uridine diphospho-delta-glucuronate	HMDB
Uridine diphospho-delta-glucuronic acid	HMDB
Uridine diphosphoglucuronate	HMDB
Uridine diphosphoglucuronic acid	HMDB
Uridine pyrophosphoglucuronate	HMDB
Uridine pyrophosphoglucuronic acid	HMDB
Uridinediphosphoglucuronic acid	HMDB
Acid, UDP glucuronic	HMDB
Acid, uridine diphosphoglucuronic	HMDB
Glucuronic acid, UDP	HMDB
Diphosphoglucuronic acid, uridine	HMDB
Uridine 5'-diphospho-alpha-D-glucuronic acid	HMDB
Uridine 5'-diphospho-α-D-glucuronic acid	HMDB
Uridine 5’-diphospho-α-D-glucuronic acid	HMDB
Uridine 5’-diphosphoglucuronic acid	HMDB
Uridine diphosphate glucuronic acid	HMDB

Chemical Formula

C₁₅H₂₂N₂O₁₈P₂

Average Molecular Weight

580.2853

Monoisotopic Molecular Weight

580.034284934

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 Name

udp-α-D-glucuronic acid

CAS Registry Number

2616-64-0

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

InChI Identifier

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

InChI Key

HDYANYHVCAPMJV-LXQIFKJMSA-N

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Endoplasmic reticulum
Golgi
Mitochondria

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
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Golgi
Mitochondria

Biospecimen Locations

Liver
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nucleotide Sugars Metabolism		Not Available
Porphyrin Metabolism		Not Available
Androgen and Estrogen Metabolism		Not Available
Starch and Sucrose Metabolism		Not Available
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000935

DrugBank ID

DB03041

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Uridine_diphosphate_glucuronic_acid

METLIN ID

5884

PubChem Compound

17473

PDB ID

Not Available

ChEBI ID

17200

References

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. J. Org. Chem., 1990, 55 (6), pp 1834–1841 DOI: 10.1021/jo00293a030

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. dTDP-D-glucose 4,6-dehydratase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Not Available
Gene Name:: TGDS
Uniprot ID:: A6QLW2
Molecular weight:: 40666.0

Reactions

Uridine diphosphate glucuronic acid → UDP-D-Xylose + Carbon dioxide	details

Enzyme Details

2. Exostosin-2

General function:: Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:: Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Appears to be a tumor suppressor. Required for the exosomal release of SDCBP, CD63 and syndecan.
Gene Name:: EXT2
Uniprot ID:: O77783
Molecular weight:: 81887.0

Enzyme Details

3. Hyaluronan synthase 2

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Catalyzes the addition of GlcNAc or GlcUA monosaccharides to the nascent hyaluronan polymer. Therefore, it is essential to hyaluronan synthesis a major component of most extracellular matrices that has a structural role in tissues architectures and regulates cell adhesion, migration and differentiation. This is one of the isozymes catalyzing that reaction and it is particularly responsible for the synthesis of high molecular mass hyaluronan. Required for the transition of endocardial cushion cells into mesenchymal cells, a process crucial for heart development. May also play a role in vasculogenesis. High molecular mass hyaluronan also play a role in early contact inhibition a process which stops cell growth when cells come into contact with each other or the extracellular matrix (By similarity).
Gene Name:: HAS2
Uniprot ID:: O97711
Molecular weight:: 63459.0

Enzyme Details

4. Exostosin-1

General function:: Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:: Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Required for the exosomal release of SDCBP, CD63 and syndecan (By similarity).
Gene Name:: EXT1
Uniprot ID:: A5D7I4
Molecular weight:: 86299.0

Enzyme Details

5. UDP-glucose 6-dehydrogenase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Catalyzes the formation of UDP-alpha-D-glucuronate, a constituent of complex glycosaminoglycans (By similarity). Required for the biosynthesis of chondroitin sulfate and heparan sulfate. Required for embryonic development via its role in the biosynthesis of glycosaminoglycans (By similarity).
Gene Name:: UGDH
Uniprot ID:: P12378
Molecular weight:: 55136.0

Reactions

Uridine diphosphate glucose + 2 NAD + Water → Uridine diphosphate glucuronic acid +2 NADH	details

Enzyme Details

6. UDP-glucuronosyltransferase 3A1

General function:: Carbohydrate transport and metabolism
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
Gene Name:: UGT3A1
Uniprot ID:: Q1LZI1
Molecular weight:: 59682.0

Reactions

Uridine diphosphate glucuronic acid → Isovalerylglucuronide + Uridine 5'-diphosphate	details

Showing metabocard for Uridine diphosphate glucuronic acid (BMDB0000935)

Structure for BMDB0000935 (Uridine diphosphate glucuronic acid)

Enzymes

Reactions

Reactions

Reactions