NP-MRD: Showing NP-Card for 2',4',6'-Trihydroxyacetophenone monohydrate (NP0331653)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2023-05-30 20:00:15 UTC

Updated at

2024-05-11 02:07:37 UTC

NP-MRD ID

NP0331653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',4',6'-Trihydroxyacetophenone monohydrate

Description

2',4',6'-Trihydroxyacetophenone, also known as 2-acetylphloroglucinol or phloracetophenone, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2',4',6'-Trihydroxyacetophenone has been detected, but not quantified in, fruits. It was first documented in 2007 (PMID: 17546658). This could make 2',4',6'-trihydroxyacetophenone a potential biomarker for the consumption of these foods (PMID: 21472649) (PMID: 22451400).

Structure

MOL 3D MOL SDF 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

View in JSmol

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	MeSH
4-mono-Hydroxy-acetophenone	MeSH
2,4,-Dihydroxy-acetophenone	MeSH
2,4,6-THA	MeSH

Chemical Formula

C₈H₈O₄

Average Mass

168.1467 Da

Monoisotopic Mass

168.04226 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-05-11	View Spectrum

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0029644

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000815

KNApSAcK ID

Not Available

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

Good Scents ID

Not Available

References

General References

Hsu NY, Yang WB, Wong CH, Lee YC, Lee RT, Wang YS, Chen CH: Matrix-assisted laser desorption/ionization mass spectrometry of polysaccharides with 2',4',6'-trihydroxyacetophenone as matrix. Rapid Commun Mass Spectrom. 2007;21(13):2137-46. doi: 10.1002/rcm.3072. [PubMed:17546658 ]
Ferreira EA, Gris EF, Rebello JM, Correia JF, de Oliveira LF, Filho DW, Pedrosa RC: The 2',4',6'-trihydroxyacetophenone isolated from Myrcia multiflora has antiobesity and mixed hypolipidemic effects with the reduction of lipid intestinal absorption. Planta Med. 2011 Sep;77(14):1569-74. doi: 10.1055/s-0030-1270956. Epub 2011 Apr 6. [PubMed:21472649 ]
Hayashi A, Saitou H, Mori T, Matano I, Sugisaki H, Maruyama K: Molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase from Pseudomonas sp. YGJ3. Biosci Biotechnol Biochem. 2012;76(3):559-66. doi: 10.1271/bbb.110860. [PubMed:22451400 ]

Showing NP-Card for 2',4',6'-Trihydroxyacetophenone monohydrate (NP0331653)

MOL for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

3D MOL for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

3D SDF for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

3D-SDF for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

PDB for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

3D PDB for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

SMILES for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

INCHI for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

Structure for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)

3D Structure for NP0331653 (2',4',6'-Trihydroxyacetophenone monohydrate)