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Showing NP-Card for Methyl vanillate (NP0000826)

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Record Information
Version2.0
Created at2018-04-09 19:42:34 UTC
Updated at2024-09-03 04:18:32 UTC
NP-MRD IDNP0000826
Natural Product DOIhttps://doi.org/10.57994/1425
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl vanillate
DescriptionMethyl vanillate is a member of the class of compounds known as m-methoxybenzoic acids and derivatives. These compounds are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Methyl vanillate is considered to be a slightly soluble in water acidic compound. Methyl vanillate can be synthesized from vanillic acid. Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Vanillic acid is also found in wine and vinegar. Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID:16899266 ). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID:11152072 , 10543794 , 11728709 , 9579070 ). Methyl vanillate has been identified in foods such as cow's milk (PMID:4682334 ) And beer (PMID:20800742 ).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0000826 (Methyl vanillate)

      
  Mrv1652305271900212D          

 13 13  0  0  0  0            999 V2000
10001.055910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7701 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.484410000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055910001.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.194710000.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4755 9999.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1947 9998.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.339210000.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.624810000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9102 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6247 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3393 9999.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  2  3  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 11  7  1  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
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3D MOL for NP0000826 (Methyl vanillate)

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3D SDF for NP0000826 (Methyl vanillate)
      
  Mrv1652305271900212D          

 13 13  0  0  0  0            999 V2000
10001.055910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7701 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.484410000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055910001.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.194710000.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4755 9999.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1947 9998.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.339210000.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.624810000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9102 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6247 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3393 9999.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  2  3  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 11  7  1  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000826

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3

> <INCHI_KEY>
BVWTXUYLKBHMOX-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.09491265747998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.5154861926666663

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.99693700044588

> <JCHEM_PKA_STRONGEST_BASIC>
-4.896925778812261

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
46.5274

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0000826 (Methyl vanillate)
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PDB for NP0000826 (Methyl vanillate)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8668.6388667.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.9718666.666   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8671.3048667.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8668.6388668.979   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.2978667.437   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.9548666.665   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8663.2978664.355   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8667.3008666.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.9668667.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.6338666.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6328665.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9668664.356   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3008665.127   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
CONECT    5    6   10                                                       
CONECT    6    5                                                            
CONECT    7   11                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    5                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0000826 (Methyl vanillate)
Download
SMILES for NP0000826 (Methyl vanillate)
COC(=O)C1=CC(OC)=C(O)C=C1
Download
INCHI for NP0000826 (Methyl vanillate)
InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
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View in JSmol
Synonyms
ValueSource
4-Hydroxy-3-methoxybenzoic acid methyl esterChEBI
Methyl 3-methoxy-4-hydroxybenzoateChEBI
Methyl vanillic acidChEBI
VANILLATEChEBI
Vanillic acid, methyl esterChEBI
4-Hydroxy-3-methoxybenzoate methyl esterGenerator
Methyl 3-methoxy-4-hydroxybenzoic acidGenerator
VANILLic acidGenerator
Vanillate, methyl esterGenerator
MethylvanillateHMDB
Methylvanillic acidHMDB
Methyl 4-hydroxy-3-methoxybenzoic acidHMDB
4-Hydroxy-3-methoxy methyl benzoateHMDB
Methyl 4-hydroxy-3-methoxybenzoateHMDB
4-Hydroxy-3-methoxy methyl benzoic acidHMDB
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Namemethyl 4-hydroxy-3-methoxybenzoate
Traditional Namevanillate
CAS Registry Number3943-74-6
SMILES
COC(=O)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
InChI KeyBVWTXUYLKBHMOX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
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
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
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, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
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 Origin
Species NameSourceReference
Acer rubrum
Annona cherimola
Anthemis auriculataPlant
Aristolochia elegans
Aristolochia foveolataPlant
Aristolochia heterophylla
Aristolochia heterophylla HemslPlant
Aristolochia kaempferi
Aristolochia kankauensis
Aristolochia manshuriensisPlant
Begonia nantoensisPlant
Cestrum parqui
Crocus sativus
Euodia fargesii
Fibraurea tinctoria
Hibiscus taiwanensisPlant
Houttuynia cordata
Hovenia dulcis
Liriodendron tulipifera
Litsea hypophaea
Melicope semecarpifoliaPlant
Phyllanthus oligospermusPlant
Rhinacanthus nasutusPlant
Spiraea formosanaPlant
Tamarix aphylla
Taraxacum formosanumPlant
Tetragonotheca repanda
Trichocolea tomentella
Vanilla planifolia Jacks.
    • Headspace Techniques Utilized for the Detection of Volatile Flavor Compounds of the Vanilla Bean....
Zingiber officinale
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids  in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentM-methoxybenzoic acids and derivatives  
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • M-methoxybenzoic acid or derivatives
    • 

  • Methoxyphenol
    • 

  • Benzoate ester
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Benzoyl
    • 

  • Phenol ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP2.12ALOGPS
logP1.52ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.53 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240266  
DrugBank IDDB08711  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029771  
KNApSAcK IDNot Available
Chemspider ID18693  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl group  
METLIN IDNot Available
PubChem Compound19844  
PDB IDNot Available
ChEBI ID46477  
Good Scents IDNot Available
References
General References
  1. Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. Epub 2006 Jul 7. [PubMed:16899266  ] 
  2. Tai A, Sawano T, Ito H: Antioxidative properties of vanillic acid esters in multiple antioxidant assays. Biosci Biotechnol Biochem. 2012;76(2):314-8. doi: 10.1271/bbb.110700. Epub 2012 Feb 7. [PubMed:22313772  ]