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Showing NP-Card for 2,5 Dihydroxyacetophenone (NP0331698)

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Record Information
Version1.0
Created at2023-06-27 16:11:25 UTC
Updated at2024-05-11 00:26:50 UTC
NP-MRD IDNP0331698
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5 Dihydroxyacetophenone
Description2',5'-Dihydroxyacetophenone, also known as 2-acetylhydroquinone or 1-(2,5-dihydroxyphenyl)-ethanone, 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',5'-Dihydroxyacetophenone is an extremely weak basic (essentially neutral) compound (based on its pKa). A mixture of dihydroxyacetophenone isomers is used in food flavouring. Potential component of FEMA 3662. 2',5'-Dihydroxyacetophenone is a mixture of dihydroxyacetophenone isomers is used in food flavouring.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0331698 (2,5 Dihydroxyacetophenone)


  Mrv0541 05061306362D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   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
    1.4289    0.8250    0.0000 C   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    1.2375    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
    0.0000    0.8250    0.0000 C   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 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
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3D MOL for NP0331698 (2,5 Dihydroxyacetophenone)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.6234    1.1372   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    0.0761    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4887   -0.6506    1.2086 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -0.1384    0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883    0.6413   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494    0.4614   -0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279    1.2809   -1.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2797   -0.5482   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -1.3310    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -1.1587    0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740   -1.9709    1.7733 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9707    0.7040   -1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    1.4110    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012    2.0277   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    1.4387   -1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    2.1365   -1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3460   -0.6969   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0876   -2.1274    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -2.6925    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
 11 19  1  0
  9 18  1  0
  8 17  1  0
  7 16  1  0
  5 15  1  0
M  END
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3D SDF for NP0331698 (2,5 Dihydroxyacetophenone)


  Mrv0541 05061306362D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   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
    1.4289    0.8250    0.0000 C   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    1.2375    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
    0.0000    0.8250    0.0000 C   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 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331698

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3

> <INCHI_KEY>
WLDWSGZHNBANIO-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.835968382890258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2,5-dihydroxyphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.5737626913333331

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.848511937739596

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.418732683683102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.122984473491084

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.4226

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,5-dihydroxyphenyl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0331698 (2,5 Dihydroxyacetophenone)

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PDB for NP0331698 (2,5 Dihydroxyacetophenone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    6    7                                                       
CONECT    5    1    7    9                                                  
CONECT    6    2    4   10                                                  
CONECT    7    4    5    8                                                  
CONECT    8    3    7   11                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0331698 (2,5 Dihydroxyacetophenone)
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SMILES for NP0331698 (2,5 Dihydroxyacetophenone)
CC(=O)C1=C(O)C=CC(O)=C1
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INCHI for NP0331698 (2,5 Dihydroxyacetophenone)
InChI=1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3
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Synonyms
ValueSource
1-(2,5-Dihydroxyphenyl)-ethanoneHMDB
1-(2,5-Dihydroxyphenyl)ethanone, 9ciHMDB
1-Acetyl-2,5-dihydroxybenzeneHMDB
2', 5'-DihydroxyacetophenoneHMDB
2',5'-Dihydroxy-acetophenoneHMDB
2,5-Dihydroxy-1-acetylbenzeneHMDB
2,5-DihydroxyacetophenoneHMDB
2,5-Dihydroxyphenyl methyl ketoneHMDB
2-Acetyl-1,4-dihydroxybenzeneHMDB
2-AcetylhydroquinoneHMDB
AcetylhydroquinoneHMDB
AcetylquinolHMDB
Ghl.PD_Mitscher_leg0.355HMDB
QuinacetophenoneHMDB
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name1-(2,5-dihydroxyphenyl)ethan-1-one
Traditional Name1-(2,5-dihydroxyphenyl)ethanone
CAS Registry NumberNot Available
SMILES
CC(=O)C1=C(O)C=CC(O)=C1
InChI Identifier
InChI=1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3
InChI KeyWLDWSGZHNBANIO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-09View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-05-09View Spectrum
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlkyl-phenylketones  
Alternative Parents
Substituents
  • Alkyl-phenylketone
    • 

  • Acetophenone
    • 

  • Aryl alkyl ketone
    • 

  • Hydroquinone
    • 

  • Benzoyl
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.21ALOGPS
logP1.57ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.42 m³·mol⁻¹ChemAxon
Polarizability14.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032629  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010573  
KNApSAcK IDNot Available
Chemspider ID9859  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10279  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available