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Showing NP-Card for 3',4'-Dihydroxyacetophenone (NP0051542)

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Record Information
Version2.0
Created at2022-04-27 22:52:11 UTC
Updated at2025-07-17 01:04:44 UTC
NP-MRD IDNP0051542
Natural Product DOIhttps://doi.org/10.57994/1443
Secondary Accession NumbersNone
Natural Product Identification
Common Name3',4'-Dihydroxyacetophenone
Description3',4'-Dihydroxyacetophenone, also known as 4-acetylpyrocatechol or 1-(3,4-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. 3',4'-Dihydroxyacetophenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3',4'-Dihydroxyacetophenone has been detected, but not quantified in, coffee and coffee products. This could make 3',4'-dihydroxyacetophenone a potential biomarker for the consumption of these foods. 3',4'-Dihydroxyacetophenone is found in Abies spectabilis, Colletotrichum gloeosporioides, Ilex pubescens var. glabra , Ophiocordyceps sinensis, Picea glauca, Picea maximowiczii, Picea obovata and Vincetoxicum atratum. A dihydroxyacetophenone that is acetophenone carrying hydroxy groups at positions 3' and 4'.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051542 (3',4'-Dihydroxyacetophenone)


  Mrv1652309272007462D          

 11 11  0  0  0  0            999 V2000
 9969.4118 9968.7690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2656 9970.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.9778 9970.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2656 9971.2381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5548 9970.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8402 9970.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.1256 9970.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.1256 9969.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8400 9968.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5548 9969.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8400 9967.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0051542 (3',4'-Dihydroxyacetophenone)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.8754    0.0910   -0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -0.7647    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.6851    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.4410    0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2664   -1.1765    1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6221   -0.9131    1.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.1250    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727    0.4380    0.3631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978    0.8835   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    1.9173   -1.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564    0.5842   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887   -0.3174   -0.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3750    0.1203   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.1062   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656   -1.9936    1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2938   -1.4928    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -0.1188    0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108    2.4597   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7080    1.1780   -1.1179 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  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0051542 (3',4'-Dihydroxyacetophenone)


  Mrv1652309272007462D          

 11 11  0  0  0  0            999 V2000
 9969.4118 9968.7690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2656 9970.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.9778 9970.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.2656 9971.2381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5548 9970.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8402 9970.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.1256 9970.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.1256 9969.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8400 9968.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.5548 9969.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.8400 9967.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051542

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
UCQUAMAQHHEXGD-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.9095791168909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3,4-dihydroxyphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.9237626913333332

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.881399031285964

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.904930960736849

> <JCHEM_PKA_STRONGEST_BASIC>
-6.326517247037356

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.42260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3',4'-dihydroxyacetophenone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0051542 (3',4'-Dihydroxyacetophenone)

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PDB for NP0051542 (3',4'-Dihydroxyacetophenone)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8609.5698608.369   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8614.8968611.441   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8616.2258610.673   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8614.8968612.978   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8613.5698610.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8612.2358611.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8610.9018610.674   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8610.9018609.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8612.2358608.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8613.5698609.134   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8612.2358606.829   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0051542 (3',4'-Dihydroxyacetophenone)
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SMILES for NP0051542 (3',4'-Dihydroxyacetophenone)
CC(=O)C1=CC=C(O)C(O)=C1
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INCHI for NP0051542 (3',4'-Dihydroxyacetophenone)
InChI=1S/C8H8O3/c1-5(9)6-2-3-7(10)8(11)4-6/h2-4,10-11H,1H3
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View in JSmol
Synonyms
ValueSource
3,4-DihydroxyacetophenoneChEBI
4-AcetylpyrocatecholChEBI
1-(3,4-Dihydroxyphenyl)-ethanoneHMDB
1-(3,4-Dihydroxyphenyl)ethanoneHMDB
1-(3,4-Dihydroxyphenyl)ethanone, 9ciHMDB
4-AcetocatecholHMDB
4-AcetopyrocatecholHMDB
Acetophenone-3',4'-dihydroxyHMDB
AcetopyrocatecholHMDB
AcetylpyrocatecholHMDB
QingxintongHMDB
1-(3,4-Dihydroxyphenyl)ethan-1-onePhytoBank
3',4'-DihydroxyacetophenonePhytoBank
3’,4’-DihydroxyacetophenonePhytoBank
4-Acetyl-1,2-benzenediolPhytoBank
4-AcetylcatecholPhytoBank
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name1-(3,4-dihydroxyphenyl)ethan-1-one
Traditional Name3',4'-dihydroxyacetophenone
CAS Registry NumberNot Available
SMILES
CC(=O)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H8O3/c1-5(9)6-2-3-7(10)8(11)4-6/h2-4,10-11H,1H3
InChI KeyUCQUAMAQHHEXGD-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 Goel2024-05-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600.13371 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View 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, 600.13371, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2025-07-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Abies spectabilisLOTUS Database
Colletotrichum gloeosporioidesLOTUS Database
Ilex pubescens var. glabraPlant
Ophiocordyceps sinensisLOTUS Database
Picea glaucaLOTUS Database
Picea maximowicziiPlant
Picea obovataLOTUS Database
Vincetoxicum atratumLOTUS Database
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
    • 

  • Catechol
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • 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
logP1.22ALOGPS
logP0.92ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.42 m³·mol⁻¹ChemAxon
Polarizability14.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029661  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000835  
KNApSAcK IDC00002693  
Chemspider ID13873  
KEGG Compound IDC10675  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14530  
PDB IDNot Available
ChEBI ID19868  
Good Scents IDNot Available
References
General References