MiMeDB: Showing metabocard for 2-acetylphloroglucinol (MMDBc0054155)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:56:23 UTC

Update Date

2022-09-01 02:27:31 UTC

Metabolite ID

MMDBc0054155

Metabolite Identification

Common Name

2-acetylphloroglucinol

Description

2',4',6'-Trihydroxyacetophenone, also known as phloracetophenone or 2-acetylphloroglucinol, 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. 2',4',6'-Trihydroxyacetophenone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2',4',6'-Trihydroxyacetophenone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   2.694   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   3.463   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.665   1.155   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.665   1.155   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -1.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -1.154   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.463   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    9                                                  
CONECT    6    2    5    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11    7   10                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
2,4,6-Trihydroxyacetophenone	ChEBI
2-Acetylphloroglucinol	ChEBI
Acetophloroglucine	ChEBI
Acetylphloroglucinol	ChEBI
Monoacetylphloroglucinol	ChEBI
Phloracetophenone	ChEBI
Phloroacetophenone	ChEBI
THAP	ChEBI
1-(2,4, 6-Trihydroxyphenyl)ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)-ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)ethanone	HMDB
1-(2,4,6-Trihydroxyphenyl)ethanone, 9ci	HMDB
2',4',6'-Trihydroxy-acetophenone	HMDB
2',4',6'-Trihydroxyacetophenone monohydrate	HMDB
2-Acetyl-1,3,5-benzenetriol	HMDB
Acetophenone, 2',4',6'-trihydroxy- (8ci)	HMDB
Acetophloroglucinol	HMDB
Phloracetophene	HMDB
2,4,6-Trihydroxy-acetophenone	HMDB
4-mono-Hydroxy-acetophenone	HMDB
2,4,-Dihydroxy-acetophenone	HMDB
2,4,6-THA	HMDB

Molecular Formula

C₈H₈O₄

Average Mass

168.1467

Monoisotopic Mass

168.042258744

IUPAC Name

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

Traditional Name

2,4,6-trihydroxyacetophenone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3

InChI Key

XLEYFDVVXLMULC-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:64344 )
aromatic ketone (CHEBI:64344 )
benzenetriol (CHEBI:64344 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.56 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.92	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.4 m³·mol⁻¹	ChemAxon
Polarizability	15.71 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-1900000000-c640fdb3756ff469be64	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0300-4139000000-b50f4bf400f878c9b3a6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-ba8cd8b451c5fac4c8a3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-d6ab8e4cefbdc9be671f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-a0fd3047a84225da61d9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-e778aaab2bdbec365d68	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-8f18bfa483c344c937b5	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-7b111e51f726ac74cf70	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-5900000000-3962c436b5c05a9a0ca3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5d9a20e0063d5bba08a8	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00or-0900000000-3a050859d59d808ae070	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-5900000000-3b9e89e6188f422938ac	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1900000000-663bacb4b0e67d970489	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fr6-6900000000-f00bfc59e2420a31ed99	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015c-9200000000-013b98101a50407d43c5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-18e61dd3d41e0b51a809	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-3900000000-ccfff7c1bcecb10eddf6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-8f870a7da2d3f8dd9297	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016982	2,4-Diacetylphloroglucinol	2-acetylphloroglucinol	2,4-diacetylphloroglucinol hydrolase	Hydrolysis of bond	RHEA	34755880

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	Proteobacteria	4	Human ; Human subgingival plaque; Human feces

Exposure Sources

Source Type	Source Sub-type	Species	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

HMDB0029644

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000815

KNApSAcK ID

C00054092

Chemspider ID

61386

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,4,6-Trihydroxyacetophenone

METLIN ID

Not Available

PubChem Compound

68073

PDB ID

Not Available

ChEBI ID

64344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 2-acetylphloroglucinol (MMDBc0054155)

MOL for #<Metabolite:0x00007f5abd7b9d68>

3D MOL for #<Metabolite:0x00007f5abd7b9d68>

3D SDF for #<Metabolite:0x00007f5abd7b9d68>

3D-SDF for #<Metabolite:0x00007f5abd7b9d68>

PDB for #<Metabolite:0x00007f5abd7b9d68>

3D PDB for #<Metabolite:0x00007f5abd7b9d68>

SMILES for #<Metabolite:0x00007f5abd7b9d68>

INCHI for #<Metabolite:0x00007f5abd7b9d68>

Structure for #<Metabolite:0x00007f5abd7b9d68>

3D Structure for #<Metabolite:0x00007f5abd7b9d68>