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Showing NP-Card for 2',4'-Dihydroxyacetophenone (NP0332196)

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Record Information
Version2.0
Created at2023-12-06 00:00:27 UTC
Updated at2024-09-03 04:18:21 UTC
NP-MRD IDNP0332196
Natural Product DOIhttps://doi.org/10.57994/1366
Secondary Accession NumbersNone
Natural Product Identification
Common Name2',4'-Dihydroxyacetophenone
Description2',4'-Dihydroxyacetophenone, also known as resacetophenone or 4-acetylresorcinol, 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'-Dihydroxyacetophenone is an extremely weak basic (essentially neutral) compound (based on its pKa). A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0332196 (2',4'-Dihydroxyacetophenone)


  Mrv0541 02241219172D          

 11 11  0  0  0  0            999 V2000
    0.3708   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0332196 (2',4'-Dihydroxyacetophenone)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.8663   -0.6848    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072    0.4299    0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    1.6143    0.2463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887    0.1688    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.1180    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -1.3769   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -0.3213   -0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -0.5309   -0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235    0.9634   -0.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857    1.1993   -0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1634    2.4864   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7736   -0.2831    1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3607   -1.3641    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1370   -1.2041   -0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -1.9456    0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425   -2.3947    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791   -0.7033   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3435    1.8231   -0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4802    3.2416   -0.4172 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  7  2  0
  7  8  1  0
  7  6  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
  6 16  1  0
  5 15  1  0
M  END
Download

3D SDF for NP0332196 (2',4'-Dihydroxyacetophenone)


  Mrv0541 02241219172D          

 11 11  0  0  0  0            999 V2000
    0.3708   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332196

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
SULYEHHGGXARJS-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.886555432258586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2,4-dihydroxyphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.5737626913333331

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.830310895555142

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.900117669532257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9066726420599727

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.422599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2',4'-dihydroxyacetophenone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0332196 (2',4'-Dihydroxyacetophenone)

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PDB for NP0332196 (2',4'-Dihydroxyacetophenone)
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       0.692  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.692  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.692  -2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.924  -1.539   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.310  -2.309   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.924  -0.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.692   0.769   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.692   2.309   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.310  -0.001   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.078   0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.078   2.309   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0332196 (2',4'-Dihydroxyacetophenone)
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SMILES for NP0332196 (2',4'-Dihydroxyacetophenone)
CC(=O)C1=C(O)C=C(O)C=C1
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INCHI for NP0332196 (2',4'-Dihydroxyacetophenone)
InChI=1S/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H3
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Synonyms
ValueSource
2,4-DihydroxyacetophenoneChEBI
4-AcetylresorcinolChEBI
ResacetophenoneChEBI
1-(2,4-Dihydroxyphenyl)-ethanoneHMDB
1-(2,4-Dihydroxyphenyl)ethanone, 9ciHMDB
2',4'-Dihydroxy-acetophenoneHMDB
4-Acetyl-1,3-benzenediolHMDB
4-Acetyl-resorcinolHMDB
ResoacetophenoneHMDB
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name1-(2,4-dihydroxyphenyl)ethan-1-one
Traditional Name2',4'-dihydroxyacetophenone
CAS Registry NumberNot Available
SMILES
CC(=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H3
InChI KeySULYEHHGGXARJS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, 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)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View 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
    • 

  • Resorcinol
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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-1.3ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.42 m³·mol⁻¹ChemAxon
Polarizability14.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029659  
DrugBank IDNot Available
Phenol Explorer Compound ID1059  
FoodDB IDFDB000833  
KNApSAcK IDC00033340  
Chemspider ID6724  
KEGG Compound IDC03663  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6990  
PDB IDNot Available
ChEBI ID18414  
Good Scents IDNot Available
References
General ReferencesNot Available