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UDP-xylose

CAT: 0804-HY-N11287Size: 1 EachDry Ice: NoHazardous: No
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Description
UDP-xylose is an endogenous sugar nucleotide and a catalytic substrate of UDP-xylose synthase (UXS) . UDP-xylose is a sugar donor for the synthesis of glycoproteins, polysaccharides, various metabolites and oligosaccharides in plants, vertebrates and fungi, and participates in the synthesis of proteoglycans as a glycosyl donor. UDP-xylose participates in the regulation of the synthesis of extracellular matrix components and can be used to study the mechanism of proteoglycan biosynthesis in glycobiology and related diseases (such as connective tissue diseases) [1][2].
CAS Number
3616-06-6
UNSPSC
12352005
Hazard Statement
H302-H315-H319-H335
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/udp-xylose.html
Solubility
10 mM in DMSO
Smiles
O[C@H]([C@H]([C@@H](CO1)O)O)[C@H]1OP(OP(OC[C@@H]2[C@@H](O)[C@@H](O)[C@H](N3C(NC(C=C3)=O)=O)O2)(O)=O)(O)=O
Molecular Formula
C14H22N2O16P2
Molecular Weight
536.28
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
References & Citations
[1]Oka T, et al. Reconstruction of de novo pathway for synthesis of UDP-glucuronic acid and UDP-xylose from intrinsic UDP-glucose in Saccharomyces cerevisiae. FEBS J. 2006 Jun;273 (12) :2645-57.|[2]Eixelsberger T, et al. Structure and mechanism of human UDP-xylose synthase: evidence for a promoting role of sugar ring distortion in a three-step catalytic conversion of UDP-glucuronic acid. J Biol Chem. 2012 Sep 7;287 (37) :31349-58.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Udp xylose

UDP-alpha-D-xylose is a UDP-sugar having alpha-xylose as the sugar component. It is an important metabolite in the nucleotide sugar metabolism in animals, plants, fungi, and bacteria. It has a role as a fundamental metabolite. It is a conjugate acid of an UDP-alpha-D-xylose(2-).

CAS Number3616-06-6
PubChem CID19235
IUPAC Name[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] hydrogen phosphate
Molecular FormulaC14H22N2O16P2
Molecular Weight536.28
XLogP-6.6
Topological Polar Surface Area271
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count8
Heavy Atom Count34
Formal Charge0
Complexity916
SMILES
C1[C@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O)O)O
InChI
InChI=1S/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6-,8+,9-,10-,11-,12-,13-/m1/s1
InChIKey
DQQDLYVHOTZLOR-OCIMBMBZSA-N
Chemical Structure
2D Structure
2D structure of Udp xylose
CAS: 3616-06-6
CID: 19235
Formula: C14H22N2O16P2
MW: 536.28
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight536.28
XLogP3-6.6
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count8
Exact Mass536.04445661
Monoisotopic Mass536.04445661
Topological Polar Surface Area271 Ų
Heavy Atom Count34
Formal Charge0
Complexity916
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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