Udp-glucuronic acid

HCID 17473
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
2616-64-0
Standard SMILES
O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey
HDYANYHVCAPMJV-LXQIFKJMSA-N
Molecular formula
C15H22N2O18P2
Average molar mass
580.28 g/mol
Monoisotopic mass
580.03428512

Overview

UDP-alpha-D-glucuronic acid is a UDP-sugar having alpha-D-glucuronic acid as the sugar component. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is functionally related to an alpha-D-glucuronic acid. It is a conjugate acid of an UDP-alpha-D-glucuronate(3-).

Names & identifiers

Preferred name
Udp-glucuronic acid
IUPAC
(2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
English name
(2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic
Molecular formula
C15H22N2O18P2
Molecular weight
580.29

Names & synonyms

Udp-glucuronic aciduridine diphosphate glucuronic acid2616-64-0UDPGAUdp glucuronic acidudp-glcuaUridine diphosphoglucuronic acidUDP-D-glucuronic acidUDP-alpha-D-glucuronic acidUridinediphosphoglucuronic acidURIDINE-5'-DIPHOSPHATE-GLUCURONIC ACID04SZC4MEFQ
Show more names
UDP-glucuronateUDP-g acidUDP-Ghucuronie AcidUDPg acid,UDP g acidUDP-α-D-glucuronicaciUDP-α-D-galacturonic acid
DTXSID00903961alpha-D-Glucopyranuronic acid, 1-P'-ester with uridine 5'-(trihydrogen diphosphate)(2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acidCHEBI:17200Uridine 5'-diphosphate alpha-D-Glucopyranuronic acid(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 acidAcid, UDP GlucuronicGlucuronic Acid, UDP

Database identifiers

CAS
2616-64-0
PubChem CID
17473
DTXSID
DTXSID00903961
ChEMBL
CHEMBL228057
ChEBI
CHEBI:17200
UNII
04SZC4MEFQ
Nikkaji
J247.699A

Properties

Computed structural properties

XLogP
-6.4
Topological polar surface area
309 Ų
Hydrogen bond donors
9
Hydrogen bond acceptors
18
Rotatable bonds
9
Heavy atoms
37

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section · 3 items

210.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

211 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

210.9 Ų [M+Na]+

Physicochemical properties

Density
2.05 · 2.05±0.1 g/cm3(Predicted)
pka
1.1 · 1.10±0.50(Predicted)
InChIKey
HDYANYHVCAPMJV-ARRNFTAONA-N
SMILES
O[C@@H]1[C@@H]([C@@H](COP(O)(=O)OP(O)(=O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(=O)O)O2)O)O[C@H]1N1C=CC(=O)NC1=O)O |&1:1,2,3,14,15,16,18,20,27,r|
CAS DataBase Reference
2616 · 2616-64-0
FDA UNII
4 SZC4MEFQ · 04SZC4MEFQ

Chemistry & industry

Pharmacology

Tissue LocationsLiver
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways17-Beta Hydroxysteroid Dehydrogenase III Deficiency

Uses & manufacturing

Uses · 1 item

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. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. [ChemIDplus]

Applications · 2 items

Uses(2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic is a sugar used in polysaccharide formation and is an intermediate in the biosynthesis of ascorbic acid.

DescriptionAn intermediate in the phase II reaction that results in the formation of glucuro_x0002_nic acid conjugates of xenobiotics which contain substituents such as hydroxyl, amino, or sulfhydryl groups, forming the O-, N-, and S-glucuronides, respectively. UDPGA is formed by two reactions: (i) the formation of UDPG from UTP and glucose 1-phosphate and (ii) the formation of UDPGA from UDPG. The two reactions are catalyzed by UDPG pyrophosphorylase and UDPG dehydrogenase, respectively, whereas glucuronide formation is catalyzed by glucuronosyltransferase. Glucuronide formation from xenobiotics is common in all animal groups except insects.

Upstream & downstream products

Suppliers74 total

上海沛灵生物科技有限公司13127581762 13127581762 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

Additional notes

DefinitionChEBI: A UDP-sugar having alpha-D-glucuronic acid as the sugar component.

Related reactions

1 records
New reaction record

Compound notes

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