Compounds > (S)-4,5-dihydroxypentane-2,3-dione
Page last updated: 2024-11-12

(S)-4,5-dihydroxypentane-2,3-dione

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

Description

(S)-4,5-dihydroxypentane-2,3-dione : Pentane substituted at the 2- and 3-positions by oxo groups, at the 4- and 5-positions by hydroxy groups and with S stereoconfiguration at C-4. [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]

Cross-References

ID SourceID
PubMed CID11170991
CHEBI ID29484
SCHEMBL ID937397

Synonyms (9)

Synonym
(4s)-4,5-dihydroxy-2,3-pentanedione
(s)-4,5-dihydroxypentane-2,3-dione
(4s)-4,5-dihydroxypentane-2,3-dione
CHEBI:29484 ,
(s)-4,5-dihydroxypentanedione
SCHEMBL937397
710324-30-4
(s)-4,5-dihydroxy-2,3-pentanedione
Q27110096
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[role 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]

Drug Classes (2)

ClassDescription
alpha-diketoneA diketone that has its two ketone functionalities on adjacent atoms.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
[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]

Pathways (5)

PathwayProteinsCompounds
autoinducer AI-2 biosynthesis I319
autoinducer AI-2 biosynthesis II (Vibrio)213
autoinducer AI-2 degradation49
L-cysteine biosynthesis VI (from L-methionine)518
S-adenosyl-L-methionine cycle I417

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Autoinducer 2-binding periplasmic protein LuxPVibrio harveyiEC50 (µMol)0.08600.03200.08600.1500AID434831; AID642419; AID642420
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID642420Agonist activity at Vibrio harveyi MM32 LuxP receptor assessed as induction of bioluminescence after 5 hrs 30 mins2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli.
AID642419Binding affinity to Vibrio harveyi CFP/YFP-tagged LuxP receptor assessed as decrease in FRET ratio2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli.
AID576626Binding affinity to LuxP in Vibrio fischeri MM32 by FRET method2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
AID576627Induction of LsrB-dependent quorum sensing in Escherichia coli KX1446 assessed as expression of Lsr system at 40 uM by beta-galactosidase reporter assay2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
AID305764Inhibition of biofilm formation in Bacillus cereus at 8 uM after 24 hrs by 96-well polyvinylchloride microtiter plate assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.
AID434838Inhibition of wild type Pseudomonas aeruginosa PAO1 growth at 100 uM2009Bioorganic & medicinal chemistry letters, Jul-15, Volume: 19, Issue:14
Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs.
AID305762Induction of bioluminescence in Vibrio harveyi after 4 hrs by beta-Gal reporter gene assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.
AID642421Antagonist activity at Vibrio harveyi MM32 LuxP receptor assessed as decrease in receptor agonist DPD-induced bioluminescence after 5 hrs 30 mins2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli.
AID642422Growth inhibition of Vibrio harveyi MM32 at 0.1 mM after 5 hrs2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli.
AID576625Induction of LuxP-dependent quorum sensing in Vibrio fischeri MM32 assessed as induction of bioluminescence intensity after 4 hrs2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
AID246191Effective concentration to induce a quorum signal in Vibrio harveyi(by binding Lux P protein)2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Quorum sensing in Vibrio harveyi: probing the specificity of the LuxP binding site.
AID472934Induction of Vibrio harveyi BB170 LuxP sensor protein-mediated quorum sensing activity at 0.5 to 5 ug/ml by reporter bioluminescence assay2010Bioorganic & medicinal chemistry letters, Apr-15, Volume: 20, Issue:8
Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer.
AID434832Agonist activity at Vibrio harveyi MM30 LuxP assessed as inhibition of autoinducer-2-induced quorum sensing2009Bioorganic & medicinal chemistry letters, Jul-15, Volume: 19, Issue:14
Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs.
AID615274Inhibition of autoinducer-stimulated quorum sensing regulated bioluminescence in Vibrio fischeri by luminescence assay2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Medicinal chemistry as a conduit for the modulation of quorum sensing.
AID434831Agonist activity at Vibrio harveyi BB170 LuxP assessed as inhibition of autoinducer-2-induced quorum sensing after 5 hrs by luminescence assay2009Bioorganic & medicinal chemistry letters, Jul-15, Volume: 19, Issue:14
Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's4 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.26

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 Index12.26 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
catechol
[no description available]		2.0510catecholsallelochemical;
genotoxin;
plant metabolite
pyrogallol
benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.		2.0510benzenetriol;
phenolic donor		plant metabolite
2,3,4-trihydroxbenzophenone
2,3,4-trihydroxbenzophenone : A benzenetriol that is benzophenone in which one of the phenyl groups is substituted by hydroxy groups at positions 2, 3, and 4. It is a redox mediator.		2.0510benzenetriol;
hydroxybenzophenone		drug metabolite;
EC 1.14.18.1 (tyrosinase) inhibitor;
human urinary metabolite;
quorum sensing inhibitor;
rat metabolite
n-(3-oxo-octanoyl)-l-homoserine lactone
N-(beta-oxooctan-1-oyl)homoserine lactone: involved in conjugation and tra gene regulation in Agrobacterium tumefaciens; structure in first source		2.0510
ribulose
ribulose: 5-carbon keto sugar; minor descriptor (75-85); on-line & Index Medicus search PENTOSES (75-85); RN given refers to (erythro)-isomer		2.0210ribuloseEscherichia coli metabolite;
human metabolite
4,5-dihydroxy-2,3-pentanedione
4,5-dihydroxy-2,3-pentanedione: structure in first source		2.0310
n-heptanoyl-homoserine lactone
N-heptanoyl-homoserine lactone: structure in first source		2.0510N-acyl-amino acid
n-(3-oxododecanoyl)homoserine lactone
N-(3-oxododecanoyl)-L-homoserine lactone : An N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent.		2.0510N-(3-oxododecanoyl)homoserine lactone;
N-acyl-L-homoserine lactone		bacterial metabolite
daphnetin
[no description available]		2.0510hydroxycoumarin
xylulose
[no description available]		2.0210xyluloseEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0210ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials