MiMeDB: Showing metabocard for UDP-beta-L-Threo-pentapyranos-4-ulose (MMDBc0031792)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:29 UTC

Update Date

2022-08-31 18:24:46 UTC

MiMeDB ID

MMDBc0031792

Metabolite Identification

Common Name

UDP-beta-L-Threo-pentapyranos-4-ulose

Description

UDP-beta-L-Threo-pentapyranos-4-ulose is an intermediate in the polymixin resistance pathway. It is a substrate for the enzyme UDP-4-amino-4-deoxy-L-arabinose aminotransferase which catalyzes the reaction UDP-4-amino-4-deoxy-beta-L-arabinopyranose + 2-oxoglutarate = UDP-beta-L-threo-pentapyranos-4-ulose + L-glutamate. Some Gram-negative bacteria, specifically Salmonella typhimurium and Escherichia coli, can become resistant to polymyxin by the modification of their lipid A structure via the attachment of 4-amino-4-deoxy-L-arabinopyranose (L-Ara4N) groups to one or more phosphate groups. This addition causes an absolute increase in lipid A charge, thus lowering the affinity of positively charged polymyxins.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
UDP-b-L-Threo-pentapyranos-4-ulose	Generator
UDP-Β-L-threo-pentapyranos-4-ulose	Generator
{[(2R,3S,4R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinate	Generator

Chemical Formula

C₁₄H₂₀N₂O₁₆P₂

Average Molecular Weight

534.2599

Monoisotopic Molecular Weight

534.028805626

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C14H20N2O16P2/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/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12?,13-/m1/s1

InChI Key

URJZIQLTPCJVMW-SVROINDSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside diphosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Cyclic ketone
Ketone
Urea
Secondary alcohol
Lactam
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25244749

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for UDP-beta-L-Threo-pentapyranos-4-ulose (MMDBc0031792)

MOL for #<Metabolite:0x000055b76dd42a40>

3D MOL for #<Metabolite:0x000055b76dd42a40>

3D SDF for #<Metabolite:0x000055b76dd42a40>

3D-SDF for #<Metabolite:0x000055b76dd42a40>

PDB for #<Metabolite:0x000055b76dd42a40>

3D PDB for #<Metabolite:0x000055b76dd42a40>

SMILES for #<Metabolite:0x000055b76dd42a40>

INCHI for #<Metabolite:0x000055b76dd42a40>

Structure for #<Metabolite:0x000055b76dd42a40>

3D Structure for #<Metabolite:0x000055b76dd42a40>