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Showing NP-Card for 3,5-Dimethoxyphenol (NP0137136)

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Record Information
Version2.0
Created at2022-05-30 16:42:44 UTC
Updated at2025-02-11 15:44:31 UTC
NP-MRD IDNP0137136
Natural Product DOIhttps://doi.org/10.57994/1237
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-Dimethoxyphenol
Description3,5-Dimethoxyphenol 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. 3,5-Dimethoxyphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-Dimethoxyphenol has been detected, but not quantified in, several different foods, such as cumins, white lupines, common salsifies, dates, and herbs and spices. This could make 3,5-dimethoxyphenol a potential biomarker for the consumption of these foods. In such a case, the intoxication can be signalized by the presence of 3,5-dimethoxyphenol in biological material (PMID: 20942244 ). Autopsy findings of fatal intoxication with yew are nonspecific. If yew decoction is consumed, plant residues are not found. A presence of plant residues in the digestive tract can signalize yew intoxication. 3,5-Dimethoxyphenol is found in Taxus baccata. 3,5-Dimethoxyphenol was first documented in 2010 (PMID: 20942244). 3,5-Dimethoxyphenol is a toxin metabolite that can be found in human consuming yew (Taxus baccata) leaves.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137136 (3,5-Dimethoxyphenol)


  Mrv1652309142020012D          

 11 11  0  0  0  0            999 V2000
    0.1787    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    1.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    1.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    0.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    1.9856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8932    1.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -0.4892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  3  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
Download

3D MOL for NP0137136 (3,5-Dimethoxyphenol)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.1714   -1.5764   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833   -0.2802   -0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4642    0.1233    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2008    1.4322    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    1.8879    0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834    3.2054    0.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529    1.0074    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172   -0.3105    0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -1.2222   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2988   -0.9162   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889   -0.7302   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -2.3363    0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843   -1.7618   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2631   -1.6798   -0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915    2.1549    0.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115    3.9268    0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485    1.3726    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761   -0.5670    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.8436   -0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195   -0.1312   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -1.7548   -0.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 11  2  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
 11 21  1  0
 10 18  1  0
 10 19  1  0
 10 20  1  0
  7 17  1  0
  6 16  1  0
  4 15  1  0
M  END
Download

3D SDF for NP0137136 (3,5-Dimethoxyphenol)


  Mrv1652309142020012D          

 11 11  0  0  0  0            999 V2000
    0.1787    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    1.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    1.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2502    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    0.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    1.9856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8932    1.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -0.4892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  3  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137136

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5,9H,1-2H3

> <INCHI_KEY>
XQDNFAMOIPNVES-UHFFFAOYSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.1632

> <EXACT_MASS>
154.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.616963506749892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dimethoxyphenol

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.3543379629999999

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.455781315690116

> <JCHEM_PKA_STRONGEST_BASIC>
-4.546341747888122

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
40.9653

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dimethoxyphenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0137136 (3,5-Dimethoxyphenol)

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PDB for NP0137136 (3,5-Dimethoxyphenol)
HEADER    PROTEIN                                 14-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-SEP-20         0                                  
HETATM    1  C   UNK     0       0.334   2.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.000   3.707   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.334   2.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.334   1.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.000   0.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.334   1.397   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.667   3.706   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.667   3.707   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.000  -0.913   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.001   2.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.001   2.937   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    3   10                                                       
CONECT    8    1   11                                                       
CONECT    9    5                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0137136 (3,5-Dimethoxyphenol)
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SMILES for NP0137136 (3,5-Dimethoxyphenol)
COC1=CC(OC)=CC(O)=C1
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INCHI for NP0137136 (3,5-Dimethoxyphenol)
InChI=1S/C8H10O3/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5,9H,1-2H3
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View in JSmol
Synonyms
ValueSource
35-DimethoxyphenolHMDB
1,3-Dimethoxy-5-hydroxybenzeneHMDB
Phloroglucinol dimethyl etherHMDB
PhloroglucindimethyletherHMDB
1-Hydroxy-3,5-dimethoxybenzeneHMDB
3,5-DimethoxyphenolHMDB
TaxicatigeninHMDB
Chemical FormulaC8H10O3
Average Mass154.1632 Da
Monoisotopic Mass154.06299 Da
IUPAC Name3,5-dimethoxyphenol
Traditional Name3,5-dimethoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=CC(OC)=CC(O)=C1
InChI Identifier
InChI=1S/C8H10O3/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5,9H,1-2H3
InChI KeyXQDNFAMOIPNVES-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 Goel2024-05-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View 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, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-04View Spectrum
Species
Species of Origin
Species NameSourceReference
Taxus baccataLOTUS 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
  • M-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Ether
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen 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
logP1.27ALOGPS
logP1.35ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.97 m³·mol⁻¹ChemAxon
Polarizability15.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059966  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030390  
KNApSAcK IDNot Available
Chemspider ID9954  
KEGG Compound IDNot Available
BioCyc IDCPD-9499  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10383  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Stribrny J, Dogosi M, Snuparek Z, Toupalik P, Balaz P, Bartos P: [3,5-dimethoxyfenol--marker intoxication with Taxus baccata]. Soud Lek. 2010 Jul;55(3):36-9. [PubMed:20942244  ]