MiMeDB: Showing metabocard for 2,4-Diacetylphloroglucinol (MMDBc0020458)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 10:34:11 UTC

Update Date

2025-10-07 16:07:06 UTC

Metabolite ID

MMDBc0020458

Metabolite Identification

Common Name

2,4-Diacetylphloroglucinol

Description

2,4-Diacetylphloroglucinol is a member of the phenolic compound class and serves as a significant metabolite in various biological systems. Its chemical structure features two acetyl groups attached to the phloroglucinol backbone, contributing to its antifungal properties. This compound is synthesized by certain plant-associated bacteria, such as Pseudomonas species, which possess genes encoding the necessary biosynthetic enzymes (PMID:40919919 ). In microbial ecosystems, 2,4-diacetylphloroglucinol is involved in complex signaling pathways, including the RetS-GacS/GacA multikinase network, which regulates its production and biocontrol activity (PMID:40537942 ). Furthermore, it plays a role in seed treatment applications, enhancing germination and growth while providing protection against post-harvest fungal pathogens like Aspergillus flavus (PMID:40528114 ). The compound has been identified in antibiosis gene screenings alongside other metabolites, highlighting its ecological relevance (PMID:40788671 ). Additionally, during wheat monoculture, the buildup of 2,4-diacetylphloroglucinol-producing pseudomonads contributes to the natural biocontrol phenomenon known as take-all decline (PMID:39970109 ). Overall, 2,4-diacetylphloroglucinol exemplifies the intersection of chemistry and biology in microbial and plant interactions.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191523312D          

 15 15  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0020458

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)C1=C(O)C(C(C)=O)=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3

> <INCHI_KEY>
PIFFQYJYNWXNGE-UHFFFAOYSA-N

> <FORMULA>
C10H10O5

> <MOLECULAR_WEIGHT>
210.185

> <EXACT_MASS>
210.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.835114261125177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3-acetyl-2,4,6-trihydroxyphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
2.777844888333333

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.632565016877036

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.433491632573263

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8435112125955664

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
52.8063

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-diacetylphloroglucinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10    4   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
1,1'-(2,4,6-Trihydroxy-1,3-phenylene)bisethanone	ChEBI
1,5-Diacetyl-2,4,6-trihydroxybenzene	ChEBI
1-(3-Acetyl-2,4,6-trihydroxyphenyl)ethanone	ChEBI
2,4,6-Trihydroxy-1,3-diacetylbenzene	ChEBI
5-Acetyl-2,4,6-trihydroxyacetophenone	ChEBI
Diacetylphloroglucinol	ChEBI
2,4-DAPG	MeSH
2,4-DiAc-phloroglucinol	MeSH

Molecular Formula

C₁₀H₁₀O₅

Average Mass

210.185

Monoisotopic Mass

210.052823422

IUPAC Name

1-(3-acetyl-2,4,6-trihydroxyphenyl)ethan-1-one

Traditional Name

2,4-diacetylphloroglucinol

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C(C(C)=O)=C(O)C=C1O

InChI Identifier

InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3

InChI Key

PIFFQYJYNWXNGE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Acetophenone
Phloroglucinol derivative
Benzenetriol
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Polyol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:78688 )
aromatic ketone (CHEBI:78688 )
benzenetriol (CHEBI:78688 )
diketone (CHEBI:78688 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.85 g/L	ALOGPS
logP	1.57	ALOGPS
logP	2.78	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.43	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.81 m³·mol⁻¹	ChemAxon
Polarizability	19.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	167.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	50.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	187.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	392.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	266.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	275.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	894.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	184.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	683.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	155.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	260.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	157.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	67.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	352.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	618.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	41.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	221.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	964.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	625.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_1	CC(=O)C1=C(O)C=C(O)C(C(C)=O)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2114.13
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O	standard non polar	2025-10-23	1292.59
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_3	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O[Si](C)(C)C	standard non polar	2025-10-23	1905.34
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_4	CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O	standard non polar	2025-10-23	1578.29
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_5	CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O[Si](C)(C)C	standard non polar	2025-10-23	1422.64
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_1	CC(=O)C1=C(O)C=C(O)C(C(C)=O)=C1O[Si](C)(C)C	standard polar	2025-10-23	2328.79
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_2	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O	standard polar	2025-10-23	2031.82
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_3	CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O[Si](C)(C)C	standard polar	2025-10-23	2433.02
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_4	CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O	standard polar	2025-10-23	2701.65
Gas Chromatography	2,4-Diacetylphloroglucinol_TMS_5	CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(C)=O)=C1O[Si](C)(C)C	standard polar	2025-10-23	2867.13

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	3	Human feces; Human sputum; Human urine; Human supragingival plaque; Human ; Human saliva; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	2	Human feces; Human sputum; Human urine; Human supragingival plaque; Human ; Human saliva; Human mucosa; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

2,4-Diacetylphloroglucinol

METLIN ID

Not Available

PubChem Compound

16547

PDB ID

Not Available

ChEBI ID

78688

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2,4-Diacetylphloroglucinol (MMDBc0020458)

MOL for #<Metabolite:0x00007f9af2d2ee18>

3D MOL for #<Metabolite:0x00007f9af2d2ee18>

3D SDF for #<Metabolite:0x00007f9af2d2ee18>

3D-SDF for #<Metabolite:0x00007f9af2d2ee18>

PDB for #<Metabolite:0x00007f9af2d2ee18>

3D PDB for #<Metabolite:0x00007f9af2d2ee18>

SMILES for #<Metabolite:0x00007f9af2d2ee18>

INCHI for #<Metabolite:0x00007f9af2d2ee18>

Structure for #<Metabolite:0x00007f9af2d2ee18>

3D Structure for #<Metabolite:0x00007f9af2d2ee18>