Compounds > 1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyran-2-ulose
Page last updated: 2024-12-09

1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyran-2-ulose

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyran-2-ulose, often referred to as **D-glucal**, is a carbohydrate derivative with a unique structure that makes it crucial for several research areas. Here's a breakdown:

**Structure and Characteristics:**

* **Anhydro:** This indicates a ring structure with an oxygen bridge between positions 1 and 6.
* **Dideoxy:** It's missing two hydroxyl groups (oxygen and hydrogen) at positions 3 and 4.
* **β-D-glycero-hex-3-enopyran:** This describes the sugar's configuration – a six-membered pyranose ring (hex) with a double bond at position 3, belonging to the D-glycero series, and in the β-anomeric form.
* **2-ulose:** It has a ketone functional group at position 2.

**Importance in Research:**

**1. Chemical Synthesis:**

* **Building Block:** D-glucal serves as a versatile starting material for synthesizing various complex carbohydrate structures, including glycosides, oligosaccharides, and even natural product analogs. Its reactivity with various reagents and its ability to undergo ring-opening reactions make it ideal for building diverse sugar structures.

**2. Bioconjugation and Drug Delivery:**

* **Linker:** The double bond in D-glucal allows it to be easily conjugated to various molecules like proteins, peptides, or drugs. This creates drug conjugates with improved properties, such as increased stability, targeted delivery, and enhanced biological activity.

**3. Carbohydrate Mimics and Inhibitors:**

* **Enzyme Probes:** The unique structure of D-glucal makes it a valuable tool for studying carbohydrate-binding enzymes. It can be used as a substrate mimic or inhibitor to understand the mechanisms of enzyme activity and develop new drugs.

**4. Materials Science:**

* **Self-Assembly:** D-glucal can form supramolecular assemblies due to its ability to hydrogen bond and interact with other molecules. This property is being explored for applications in materials science, such as creating new polymers and nanomaterials.

**5. Biology and Glycobiology:**

* **Glycosylation Studies:** D-glucal analogs can be incorporated into glycans, which are complex sugar structures found on proteins and lipids. This allows researchers to investigate the role of glycosylation in biological processes and disease.

**In summary, 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyran-2-ulose (D-glucal) is a valuable tool in various research fields due to its unique structural features, reactivity, and ability to be modified. Its applications range from chemical synthesis and drug development to materials science and biological studies.**

1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID699486
CHEMBL ID4126941
CHEBI ID30999
SCHEMBL ID7155405
MeSH IDM0501086

Synonyms (36)

Synonym
6,8-dioxabicyclo(3.2.1)oct-2-en-4-one, (1s)-
brn 4859778
ccris 4274
37112-31-5
CHEBI:30999
(1s)-6,8-dioxabicyclo(3.2.1)oct-2-en-4-one
levoglucosenone
(1s,5r)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyranos-2-ulose
(1s)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
AKOS006345460
1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
b7n23sn1lb ,
unii-b7n23sn1lb
1,6-anhydro-3,4-dideoxy-beta-d-glycero-hex-3-enopyran-2-ulose
SCHEMBL7155405
L0150
HITOXZPZGPXYHY-UJURSFKZSA-N
PS-4213
W-202534
levoglucosenone [mi]
1,6-anhydro-3,4-dideoxy-.beta.-d-glycero-hex-3-enopyranos-2-ulose
levoglucosenone, (-)-
6,8-dioxabicyclo(3.2.1)oct-2-en-4-one, (1s,5r)-
1,6-anhydro-3,4-dideoxy-.delta.3-.beta.-d-pyranosen-2-one
levoglucosenone, >=95% (gc)
BCP07825
Q27114054
chembl4126941 ,
bdbm50276378
BB 0322953
T72379
A856725
6,8-dioxabicyclo3.2.1oct-2-en-4-one, (1s,5r)-
CS-0016272
HY-21226
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
anhydrohexoseAny anhydro sugar formally arising by elimination of water from two hydroxy groups of a single molecule of a hexose or hexose derivative.
deoxyketohexoseAny ketohexose having at least one hydroxy group replaced by hydrogen.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NACHT, LRR and PYD domains-containing protein 3 Mus musculus (house mouse)IC50 (µMol)1.20000.00041.441910.0000AID1498932
NACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)IC50 (µMol)6.60000.00502.180410.0000AID1498934
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
pattern recognition receptor signaling pathwayNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of acute inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of type 2 immune responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
apoptotic processNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
defense responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
osmosensory signaling pathwayNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
detection of biotic stimulusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of interleukin-1 beta productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of interleukin-1 beta productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of interleukin-4 productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
NLRP3 inflammasome complex assemblyNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
innate immune responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of T-helper 2 cell differentiationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein homooligomerizationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein maturationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
pyroptosisNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cellular response to lipopolysaccharideNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cellular response to virusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of non-canonical NF-kappaB signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of T-helper 2 cell cytokine productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of cysteine-type endopeptidase activity involved in apoptotic processNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
protein bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ATP bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ATP hydrolysis activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein-macromolecule adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
signaling adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
identical protein bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
peptidoglycan bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ADP bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
sequence-specific DNA bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
molecular adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
phosphatidylinositol-4-phosphate bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
DNA-binding transcription factor bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
small molecule sensor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cysteine-type endopeptidase activator activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
molecular condensate scaffold activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
phosphatidylinositol phosphate bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
cytosolNACHT, LRR and PYD domains-containing protein 3 Mus musculus (house mouse)
cytoplasmNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytosolNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
membraneNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
Golgi membraneNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
extracellular regionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
nucleusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytoplasmNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
mitochondrionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
endoplasmic reticulumNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
microtubule organizing centerNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytosolNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
interphase microtubule organizing centerNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
NLRP3 inflammasome complexNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1498932Inhibition of nigericin-induced NLRP3 inflammasome activation in C57BL/6 mouse bone marrow derived macrophages assessed as reduction in LPS-stimulated IL-1beta secretion incubated for 1 hr followed by nigericin addition measured after 1 hr by ELISA2018Bioorganic & medicinal chemistry, 07-30, Volume: 26, Issue:13
Synthesis of 1,5-Anhydro-d-fructose derivatives and evaluation of their inflammasome inhibitors.
AID1636613Cytotoxicity against human HuH7 cells assessed as reduction in cell growth after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines.
AID1636614Cytotoxicity against human HepG2 cells assessed as reduction in cell growth after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Cytotoxic effect of levoglucosenone and related derivatives against human hepatocarcinoma cell lines.
AID1498934Inhibition of nigericin-induced NLRP3 inflammasome activation in PMA-differentiated human THP1 cells assessed as reduction in LPS-stimulated IL-1beta secretion incubated for 1 hr prior to stimulation with nigericin for 1 hr by quanti-blue based SEAP repor2018Bioorganic & medicinal chemistry, 07-30, Volume: 26, Issue:13
Synthesis of 1,5-Anhydro-d-fructose derivatives and evaluation of their inflammasome inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.13)18.7374
1990's0 (0.00)18.2507
2000's7 (21.88)29.6817
2010's16 (50.00)24.3611
2020's8 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.27 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other30 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.0710elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
phosphoric acid
phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.		2.0710phosphoric acidsalgal metabolite;
fertilizer;
human metabolite;
NMR chemical shift reference compound;
solvent
sulfuric acid
sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.		2.7830sulfur oxoacidcatalyst
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.1310nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
furaldehyde
Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.		4.3340aldehyde;
furans		Maillard reaction product;
metabolite
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.4420cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		2.2510isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
titanium
Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.		2.110titanium group element atom
zirconium
Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.		2.0610titanium group element atom
titanium dioxide
titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.		2.110titanium oxidesfood colouring
thomsen-friedenreich antigen
Thomsen-Friedenreich antigen: do not confuse with T antigens, which are viral		3.1310
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.25101,2,3-triazole
5-thio-d-glucose
5-thio-D-glucose: RN given refers to 5-thio-D-glucose		2.1510
1,5-anhydrofructose
1,5-anhydrofructose: structure given in first source		2.17103-pyrones;
anhydrohexose;
cyclic ether;
cyclic ketone;
organic heterocyclic compound;
triol
lignin
Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.		2.610
sorafenib
[no description available]		2.1310(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
phenylureas;
pyridinecarboxamide		angiogenesis inhibitor;
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
ferroptosis inducer;
tyrosine kinase inhibitor
5-hydroxymethylfurfural
5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.		4.0630arenecarbaldehyde;
furans;
primary alcohol		indicator;
Maillard reaction product
D-fructopyranose
[no description available]		2.1510cyclic hemiketal;
D-fructose;
fructopyranose		sweetening agent
aluminum
Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.		2.0410boron group element atom;
elemental aluminium;
metal atom
tetrodotoxin
Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.		2.0310azatetracycloalkane;
oxatetracycloalkane;
quinazoline alkaloid		animal metabolite;
bacterial metabolite;
marine metabolite;
neurotoxin;
voltage-gated sodium channel blocker
cellulose
DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.		3.3760glycoside
smectite
smecta: used therapeutically in chronic gastritis. montmorillonite : An aluminosilicate mineral consisting of aluminosilicate layers approximately 1 nm thick which are surface-substituted with metal cations and stacked in ca. 10 mum-sized multilayer stacks. Its approximate formula is R(+)0.33(Al,Mg)2Si4O10(OH)2.nH2O where R(+) includes one or more of the cations Na(+), K(+), Mg(2+), and Ca(2+).		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Liver
[description not available]		02.1310
Liver Neoplasms
Tumors or cancer of the LIVER.		02.1310
Breast Cancer
[description not available]		02.4110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4110
Cancer of Cervix
[description not available]		02.1510
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		02.1510
Abnormalities, Autosome
[description not available]		01.9710