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Showing NP-Card for Mequinol (NP0045446)

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Record Information
Version2.0
Created at2022-03-17 19:20:06 UTC
Updated at2022-03-17 19:20:06 UTC
NP-MRD IDNP0045446
Secondary Accession NumbersNone
Natural Product Identification
Common NameMequinol
DescriptionMequinol, also known as 4-hydroxyanisole or 4-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Mequinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Mequinol is a phenolic tasting compound. Outside of the human body, Mequinol has been detected, but not quantified in, anises and sweet marjorams. This could make mequinol a potential biomarker for the consumption of these foods. Conversely, tretinoin has been observed to serve as a potent inhibitor of mammalian GSTs and to be capable of reducing the level of intracellular GSH in various cells. Such products are not indicated for oral ingestion. Nevertheless, skin cells are naturally capable of protecting themselves against such cytotoxic entities by endogenous intracellular glutathione (GSH). Regardless, it is consequently by way of this seemingly negative and damaging pharmacodynamic profile by which the mechanism of action of mequinol is sometimes described. Urine samples from melanoma patients treated with mequinol were analyzed and various mequinol metabolites were identified, including 3,4-dihydroxyanisole, the two o-methyl derivatives 3-hydroxy-4-methoxyanisole and 4-hydroxy-3-methoxyanisole, and even hydroquinone which may have originated at least partly from mequinol. It is used as an inhibitor for acrylic monomers and acrylonitirles, as a stabilizer for chlorinated hydrocarbons and ethyl cellulose, as an ultraviolet inhibitor, as a chemical intermediate in the manufacture of antioxidants, pharmaceuticals, plasticizers, and dyestuffs. Mequinol is found in Ascia monuste, Dorstenia turbinata, Glycyrrhiza glabra, Ophiocordyceps sinensis, Pyrola media and Senna corymbosa. Mequinol is in fact considered a melanocytotoxic chemical which when oxidized in melanocytes results in the formation of toxic entities like quinones.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045446 (Mequinol)


  Mrv0541 02241217322D          

  9  9  0  0  0  0            999 V2000
    1.4294   -0.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    1.2382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
Download

3D MOL for NP0045446 (Mequinol)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.8920   -0.4114    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    0.7159    0.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884    0.4607    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1527    1.5411   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    1.3315   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781    0.0797   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575   -0.0645   -0.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2190   -0.9926    0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -0.8025    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8847   -0.0219    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934   -0.9770    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483   -1.0361   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477    2.5689   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    2.1920   -0.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9279   -0.9354   -0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374   -1.9973    0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -1.6511    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0045446 (Mequinol)


  Mrv0541 02241217322D          

  9  9  0  0  0  0            999 V2000
    1.4294   -0.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    1.2382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

> <INCHI_KEY>
NWVVVBRKAWDGAB-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.1372

> <EXACT_MASS>
124.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.762679643524663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methoxyphenol

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.5120092286666669

> <ALOGPS_LOGS>
-0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.940502868815058

> <JCHEM_PKA_STRONGEST_BASIC>
-4.81035092669965

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
34.5021

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxyphenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045446 (Mequinol)

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PDB for NP0045446 (Mequinol)
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  O   UNK     0       2.668  -0.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.668  -2.311   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.668   2.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001   2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.001  -0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   0.001   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1                                                            
CONECT    3    4                                                            
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0045446 (Mequinol)
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SMILES for NP0045446 (Mequinol)
COC1=CC=C(O)C=C1
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INCHI for NP0045446 (Mequinol)
InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
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Synonyms
ValueSource
4-HydroxyanisoleHMDB
HQMME; hydroxyquinone methyl etherHMDB
Menthyl anthranilateHMDB
Novo-dermoquinonaHMDB
Leucodine bHMDB
BMS-181158P-GuaiacolHMDB
p-HydroxyanisoleHMDB
4-MethoxyphenolHMDB
4HAHMDB
LeucobasalHMDB
MechinolumHMDB
Menthyl anthranilic acidHMDB
1-Hydroxy-4-methoxybenzeneHMDB
4-Methoxy-phenolHMDB
HydroxyanisoleHMDB
Hydroxyquinone methyl etherHMDB
Mequinol, inn, usanHMDB
mono Methyl ether hydroquinoneHMDB
Monomethyl ether hydroquinoneHMDB
p-HydroxymethoxybenzeneHMDB
p-MethoxyphenolHMDB
Para-methoxyphenolHMDB
4-Hydroxyanisole, sodium saltMeSH
Hydroquinone monomethyl etherMeSH
4-Hydroxyanisole, potassium saltMeSH
Hydroquinone methyl etherMeSH
Leucodinine bMeSH
HQMME
Chemical FormulaC7H8O2
Average Mass124.1372 Da
Monoisotopic Mass124.05243 Da
IUPAC Name4-methoxyphenol
Traditional Namemethoxyphenol
CAS Registry Number150-76-5
SMILES
COC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
InChI KeyNWVVVBRKAWDGAB-UHFFFAOYSA-N
Experimental Spectra
Not Available
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
Not Available
Species
Species of Origin
Species NameSourceReference
Ascia monusteLOTUS Database
Dorstenia turbinataPlant
Glycyrrhiza glabraLOTUS Database
Ophiocordyceps sinensisLOTUS Database
Origanum majoranaFooDB
Pimpinella anisumFooDB
Pyrola mediaLOTUS Database
Senna corymbosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassMethoxyphenols  
Direct ParentMethoxyphenols  
Alternative Parents
Substituents
  • Methoxyphenol
    • 

  • 4-alkoxyphenol
    • 

  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP1.31ALOGPS
logP1.51ChemAxon
logS-0.54ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029696  
DrugBank IDDB09516  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000886  
KNApSAcK IDC00035022  
Chemspider ID8665  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMequinol  
METLIN IDNot Available
PubChem Compound9015  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available