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Showing NP-Card for 3,4-Dimethoxybenzyl alcohol (NP0074343)

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Record Information
Version2.0
Created at2022-04-28 19:30:54 UTC
Updated at2022-04-28 19:30:54 UTC
NP-MRD IDNP0074343
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-Dimethoxybenzyl alcohol
Description(3,4-Dimethoxyphenyl)methanol, also known as veratryl alcohol or 3,4-dimethoxybenzyl alcohol, belongs to the class of organic compounds known as dimethoxybenzenes. 3,4-Dimethoxybenzyl alcohol is found in Croton lechleri, Croton lechleri Mull.Arg. and Cucurbita pepo. 3,4-Dimethoxybenzyl alcohol was first documented in 1986 (PMID: 3717546). These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups (3,4-dimethoxyphenyl)methanol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 11164314) (PMID: 12730009) (PMID: 16349197) (PMID: 7673205).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074343 (3,4-Dimethoxybenzyl alcohol)


  Mrv1533004231518292D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   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
    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 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
    0.7145   -0.4125    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   -1.6500    0.0000 O   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
    0.0000    0.8250    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0074343 (3,4-Dimethoxybenzyl alcohol)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.6781   -2.4933    0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673   -1.1202    0.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0515   -0.6818    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -1.5951    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -1.2145    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741    0.1329   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.5993   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -0.5018   -0.0001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288    1.0513   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    0.6705   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8056    1.6181   -0.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5658    2.9935   -0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -2.9746   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739   -2.6121    0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -2.8938    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343   -2.6717    0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0989   -1.9472    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158    1.1631   -0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353    1.2663    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8443   -0.9175    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    2.1041   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1924    3.3622    0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385    3.4955   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    3.1668   -0.9917 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
  7  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 12 22  1  0
 12 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0074343 (3,4-Dimethoxybenzyl alcohol)


  Mrv1533004231518292D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   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
    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 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
    0.7145   -0.4125    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   -1.6500    0.0000 O   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
    0.0000    0.8250    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074343

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CO)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5,10H,6H2,1-2H3

> <INCHI_KEY>
OEGPRYNGFWGMMV-UHFFFAOYSA-N

> <FORMULA>
C9H12O3

> <MOLECULAR_WEIGHT>
168.192

> <EXACT_MASS>
168.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.779689180799803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3,4-dimethoxyphenyl)methanol

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
0.8905535173333333

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.952289685018556

> <JCHEM_PKA_STRONGEST_BASIC>
-2.819668491772882

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
45.80030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
veratryl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0074343 (3,4-Dimethoxybenzyl alcohol)

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PDB for NP0074343 (3,4-Dimethoxybenzyl alcohol)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0074343 (3,4-Dimethoxybenzyl alcohol)
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SMILES for NP0074343 (3,4-Dimethoxybenzyl alcohol)
COC1=CC=C(CO)C=C1OC
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INCHI for NP0074343 (3,4-Dimethoxybenzyl alcohol)
InChI=1S/C9H12O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5,10H,6H2,1-2H3
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View in JSmol
Synonyms
ValueSource
3,4-DimethoxybenzenemethanolChEBI
3,4-Dimethoxybenzyl alcoholChEBI
3,4-Dimethoxyphenylmethyl alcoholChEBI
Veratrole alcoholChEBI
Veratryl alcoholChEBI
3,4-Dimethoxy benzenemethanolMeSH
Chemical FormulaC9H12O3
Average Mass168.1920 Da
Monoisotopic Mass168.07864 Da
IUPAC Name(3,4-dimethoxyphenyl)methanol
Traditional Nameveratryl alcohol
CAS Registry NumberNot Available
SMILES
COC1=CC=C(CO)C=C1OC
InChI Identifier
InChI=1S/C9H12O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5,10H,6H2,1-2H3
InChI KeyOEGPRYNGFWGMMV-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
Croton lechleriLOTUS Database
Croton lechleri Mull.Arg.Plant
Cucurbita pepoLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassMethoxybenzenes  
Direct ParentDimethoxybenzenes  
Alternative Parents
Substituents
  • O-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Benzyl alcohol
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP0.89ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.8 m³·mol⁻¹ChemAxon
Polarizability17.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-12798  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7118  
PDB IDNot Available
ChEBI ID62150  
Good Scents IDNot Available
References
General References
  1. Suguimoto HH, Barbosa AM, Dekker RF, Castro-Gomez RJ: Veratryl alcohol stimulates fruiting body formation in the oyster mushroom, Pleurotus ostreatus. FEMS Microbiol Lett. 2001 Jan 15;194(2):235-8. doi: 10.1111/j.1574-6968.2001.tb09475.x. [PubMed:11164314  ] 
  2. Lee K, Moon SH: Electroenzymatic oxidation of veratryl alcohol by lignin peroxidase. J Biotechnol. 2003 May 8;102(3):261-8. doi: 10.1016/s0168-1656(03)00027-0. [PubMed:12730009  ] 
  3. Jensen KA, Evans KM, Kirk TK, Hammel KE: Biosynthetic Pathway for Veratryl Alcohol in the Ligninolytic Fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1994 Feb;60(2):709-14. doi: 10.1128/aem.60.2.709-714.1994. [PubMed:16349197  ] 
  4. Leisola MS, Schmidt B, Fiechter A: Enzymatic determination of veratryl alcohol. Anal Biochem. 1986 May 15;155(1):108-11. doi: 10.1016/0003-2697(86)90233-2. [PubMed:3717546  ] 
  5. Koduri RS, Tien M: Oxidation of guaiacol by lignin peroxidase. Role of veratryl alcohol. J Biol Chem. 1995 Sep 22;270(38):22254-8. doi: 10.1074/jbc.270.38.22254. [PubMed:7673205  ]