ChemFOnt: Showing chemical card for UDP-N-acetyl-alpha-D-glucosamine (CFc000284042)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:51 UTC

Chemfont ID

CFc000284042

Molecule Identification

Common Name

UDP-N-acetyl-alpha-D-glucosamine

Definition

Udp-n-acetyl-alpha-d-glucosamine is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-n-acetyl-alpha-d-glucosamine is soluble (in water) and a moderately acidic compound (based on its pKa). Udp-n-acetyl-alpha-d-glucosamine can be found in a number of food items such as daikon radish, napa cabbage, wasabi, and avocado, which makes udp-n-acetyl-alpha-d-glucosamine a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-[2-({[({[3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidic acid	Generator

Chemical Formula

C₁₇H₂₅N₃O₁₇P₂

Average Molecular Weight

605.34

Monoisotopic Molecular Weight

605.067017513

IUPAC Name

[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

Traditional Name

[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxyphosphonate

CAS Registry Number

528-04-1

SMILES

CC(=O)NC1C(O)C(O)C(CO)OC1OP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/p-2

InChI Key

LFTYTUAZOPRMMI-UHFFFAOYSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Acetamide
Tetrahydrofuran
Heteroaromatic compound
Urea
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a UDP-sugar (UDP-N-ACETYL-GALACTOSAMINE )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	21.1 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-5.3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	306.07 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.31 m³·mol⁻¹	ChemAxon
Polarizability	50.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0304526

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031241

KNApSAcK ID

Not Available

Chemspider ID

3287432

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4072370

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for UDP-N-acetyl-alpha-D-glucosamine (CFc000284042)

MOL for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

3D MOL for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

3D SDF for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

3D-SDF for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

PDB for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

3D PDB for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

SMILES for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

INCHI for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

Structure for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)

3D Structure for CFc000284042 (UDP-N-acetyl-alpha-D-glucosamine)