NP-MRD: Showing NP-Card for 2,4-Diacetylphloroglucinol (NP0006139)

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Record Information

Version

2.0

Created at

2020-12-09 03:11:48 UTC

Updated at

2021-07-15 16:53:57 UTC

NP-MRD ID

NP0006139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-Diacetylphloroglucinol

Provided By

NPAtlas

Description

2,4-Diacetylphloroglucinol, also known as 2,4-dapg, 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-Diacetylphloroglucinol 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. 2,4-Diacetylphloroglucinol is found in Pseudomonas, Pseudomonas fluorescens and Pseudomonas protegens. 2,4-Diacetylphloroglucinol was first documented in 1992 (PMID: 16348633). Based on a literature review a small amount of articles have been published on 2,4-diacetylphloroglucinol (PMID: 15826166) (PMID: 18058176) (PMID: 22448105).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118253D          

 25 25  0  0  0  0            999 V2000
   -3.3882   -0.9563   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554   -1.2725   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.5042   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835   -0.2330   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469    1.0901   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775    1.4179   -0.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    2.0613   -0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508    1.7921    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    2.8625    0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    0.4641    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773    0.1070    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0966   -1.3295    0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543    0.9920    0.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352   -0.5533    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818   -1.8346    0.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -0.4132   -1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871   -0.4081    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981   -1.8947   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0093    2.3481   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    3.0994   -0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7257    2.8931    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5910   -1.8229    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2114   -1.3694    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -1.8151   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -2.7210    0.1270 H   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  1  0  0  0  0
 11 13  2  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14  4  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  6 19  1  0  0  0  0
  7 20  1  0  0  0  0
  9 21  1  0  0  0  0
 12 22  1  0  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 15 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C(=O)C([H])([H])[H])C(O[H])=C1C(=O)C([H])([H])[H]

> <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>
19.932433975274474

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.388  -0.956  -0.697  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.955  -1.272  -0.393  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.678  -2.504  -0.318  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.984  -0.233  -0.204  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.347   1.090  -0.299  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.678   1.418  -0.582  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.401   2.061  -0.115  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.951   1.792   0.172  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.786   2.862   0.332  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.304   0.464   0.265  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.677   0.107   0.558  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.097  -1.329   0.666  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.554   0.992   0.729  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.335  -0.553   0.077  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.782  -1.835   0.188  0.00  0.00           O+0
HETATM   16  H   UNK     0      -3.477  -0.413  -1.650  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.787  -0.408   0.174  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.998  -1.895  -0.748  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.009   2.348  -0.665  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.700   3.099  -0.192  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.726   2.893   0.528  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.591  -1.823   1.494  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.211  -1.369   0.865  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.958  -1.815  -0.313  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.430  -2.721   0.127  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   19                                                       
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   21                                                       
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   22   23   24                                             
CONECT   13   11                                                            
CONECT   14   10   15    4                                                  
CONECT   15   14   25                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    6                                                            
CONECT   20    7                                                            
CONECT   21    9                                                            
CONECT   22   12                                                            
CONECT   23   12                                                            
CONECT   24   12                                                            
CONECT   25   15                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol View NMR Assignments

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

Chemical Formula

C₁₀H₁₀O₅

Average Mass

210.1850 Da

Monoisotopic Mass

210.05282 Da

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

Experimental Spectra

Not Available

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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas	NPAtlas	16348633
Pseudomonas fluorescens	LOTUS Database	35616633
Pseudomonas protegens	LOTUS Database	35616633

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 )

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	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	19.93 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

NPAtlas ID

NPA020441

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

15687

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

Good Scents ID

Not Available

References

General References

Shanahan P, O'sullivan DJ, Simpson P, Glennon JD, O'gara F: Isolation of 2,4-diacetylphloroglucinol from a fluorescent pseudomonad and investigation of physiological parameters influencing its production. Appl Environ Microbiol. 1992 Jan;58(1):353-8. doi: 10.1128/AEM.58.1.353-358.1992. [PubMed:16348633 ]
Achkar J, Xian M, Zhao H, Frost JW: Biosynthesis of phloroglucinol. J Am Chem Soc. 2005 Apr 20;127(15):5332-3. doi: 10.1021/ja042340g. [PubMed:15826166 ]
Brucker RM, Baylor CM, Walters RL, Lauer A, Harris RN, Minbiole KP: The identification of 2,4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus. J Chem Ecol. 2008 Jan;34(1):39-43. doi: 10.1007/s10886-007-9352-8. Epub 2007 Dec 6. [PubMed:18058176 ]
Islam MT, von Tiedemann A: 2,4-Diacetylphloroglucinol suppresses zoosporogenesis and impairs motility of Peronosporomycete zoospores. World J Microbiol Biotechnol. 2011 Sep;27(9):2071-2079. doi: 10.1007/s11274-011-0669-7. Epub 2011 Feb 2. [PubMed:22448105 ]

Showing NP-Card for 2,4-Diacetylphloroglucinol (NP0006139)

MOL for NP0006139 (2,4-Diacetylphloroglucinol)

3D MOL for NP0006139 (2,4-Diacetylphloroglucinol)

3D SDF for NP0006139 (2,4-Diacetylphloroglucinol)

3D-SDF for NP0006139 (2,4-Diacetylphloroglucinol)

PDB for NP0006139 (2,4-Diacetylphloroglucinol)

3D PDB for NP0006139 (2,4-Diacetylphloroglucinol)

SMILES for NP0006139 (2,4-Diacetylphloroglucinol)

INCHI for NP0006139 (2,4-Diacetylphloroglucinol)

Structure for NP0006139 (2,4-Diacetylphloroglucinol)

3D Structure for NP0006139 (2,4-Diacetylphloroglucinol)