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Showing NP-Card for Vanillic acid (NP0000013)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-11-30 03:36:57 UTC
NP-MRD IDNP0000013
Secondary Accession NumbersNone
Natural Product Identification
Common NameVanillic acid
DescriptionVanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. (PMID: 16899266 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0000013 (Vanillic acid)


  Mrv1652309272007382D          

 12 12  0  0  0  0            999 V2000
10021.645810020.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310022.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.221710022.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310023.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210022.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076810022.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362310022.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362210021.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210021.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791110019.7339    0.0000 C   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
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000013 (Vanillic acid)

HMDB0000484
     RDKit          3D
Vanillic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.6049   -1.3196    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208    0.0384    0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.4308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369   -0.5004   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -0.0880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -1.0451   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -0.6560   -0.4172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -2.4090   -0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826    1.2668   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    2.2025   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.7858    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    2.7118    0.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.8824   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.7969    1.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -1.3890   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864   -1.5527   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8252   -3.0766    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.6061   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8840    3.2755    0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364    2.3980    0.3250 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  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000013 (Vanillic acid)


  Mrv1652309272007382D          

 12 12  0  0  0  0            999 V2000
10021.645810020.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310022.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.221710022.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.505310023.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210022.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076810022.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362310022.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.362210021.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.791210021.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.076710020.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.791110019.7339    0.0000 C   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
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
WKOLLVMJNQIZCI-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.860742490127857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-methoxybenzoic acid

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.1695921366666666

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.135539077333167

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.155416072405767

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901377890748089

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
41.7583

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000013 (Vanillic acid)

Download
PDB for NP0000013 (Vanillic acid)
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    8707.0728705.813   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8712.4108708.895   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8713.7478708.124   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8712.4108710.436   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8711.0778708.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8709.7438708.893   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8708.4108708.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8708.4098706.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8709.7438705.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8711.0778706.583   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8709.7438704.273   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8711.0778703.503   0.000  0.00  0.00           C+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   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0000013 (Vanillic acid)
Download
SMILES for NP0000013 (Vanillic acid)
COC1=CC(=CC=C1O)C(O)=O
Download
INCHI for NP0000013 (Vanillic acid)
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
Download
View in JSmol
Synonyms
ValueSource
4-Hydroxy-3-methoxybenzoic acidChEBI
4-Hydroxy-3-methoxybenzoateKegg
VanillateGenerator
3-Methoxy-4-hydroxybenzoateHMDB
3-Methoxy-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methoxy-benzoateHMDB
4-Hydroxy-3-methoxy-benzoic acidHMDB
4-Hydroxy-m-anisateHMDB
4-Hydroxy-m-anisic acidHMDB
Acide vanilliqueHMDB
p-VanillateHMDB
p-Vanillic acidHMDB
Protocatechuic acid 3-methyl esterHMDB
Acid, 4-hydroxy-3-methoxybenzoicHMDB
p Hydroxy m methoxy benzoic acidHMDB
4 Hydroxy 3 methoxybenzoic acidHMDB
Acid, vanillicHMDB
Acid, p-hydroxy-m-methoxy-benzoicHMDB
p-Hydroxy-m-methoxy-benzoic acidHMDB
2-Methoxy-4-carboxyphenolHMDB
Methylprotocatechuic acidHMDB
VAHMDB
m-Methoxy-p-hydroxy-benzoic acidHMDB
Vanillic acidKEGG
Chemical FormulaC8H8O4
Average Mass168.1480 Da
Monoisotopic Mass168.04226 Da
IUPAC Name4-hydroxy-3-methoxybenzoic acid
Traditional Namevanillic acid
CAS Registry Number121-34-6
SMILES
COC1=C(O)C=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
InChI KeyWKOLLVMJNQIZCI-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, simulated)Varshavi.d262021-10-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Abies nephrolepisLOTUS Database
Abies pinsapoLOTUS Database
Abutilon indicumPlant
Acer barbinerveLOTUS Database
Acer nikoenseKNApSAcK Database
Achillea millefoliumLOTUS Database
Achlys triphyllaLOTUS Database
Actinidia chinensisLOTUS Database
Aeginetia indicaLOTUS Database
Aganosma caryophyllata-
Aglaia odorataLOTUS Database
Ailanthus altissimaLOTUS Database
Ailanthus integrifoliaKNApSAcK Database
Ajuga decumbensLOTUS Database
Ajuga lupulinaLOTUS Database
Ajuga taiwanensisKNApSAcK Database
Alchemilla tianschanicaLOTUS Database
Alibertia macrophyllaLOTUS Database
Allium cepaFooDB
Allium fistulosumLOTUS Database
Allium sativumKNApSAcK Database
Alnus japonicaKNApSAcK Database
Althaea armeniacaLOTUS Database
Althaea officinalisLOTUS Database
Amburana cearensisKNApSAcK Database
Amphibolis antarcticaKNApSAcK Database
Amphibolis griffithiiKNApSAcK Database
Anastatica hierochunticaLOTUS Database
Anethum graveolensFooDB
Angelica sinensisLOTUS Database
Anigozanthos preissiiLOTUS Database
Annona cherimolaLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Aristolochia cucurbitifoliaLOTUS Database
Aristolochia kaempferiLOTUS Database
Aristolochia manshuriensisKNApSAcK Database
Aristolochia pubescensKNApSAcK Database
Aristolochia tomentosaLOTUS Database
Armoracia rusticanaFooDB
Artemisia capillarisLOTUS Database
Artemisia dracunculusFooDB
Artemisia jacuticaLOTUS Database
Artocarpus heterophyllusLOTUS Database
Asarum sieboldiiLOTUS Database
Aspalathus linearisLOTUS Database
Aster indicusLOTUS Database
Atractylodes lanceaLOTUS Database
Avena fatuaLOTUS Database
Avena sativaLOTUS Database
Avena sativa L.FooDB
Balanites aegyptiacaLOTUS Database
Bauhinia purpureaLOTUS Database
Begonia nantoensisKNApSAcK Database
Berberis koreanaLOTUS Database
Berchemia racemosaLOTUS Database
Beta vulgarisLOTUS Database
Beta vulgaris ssp. ciclaFooDB
Betula pendulaLOTUS Database
Betula pubescensLOTUS Database
Bhesa paniculataLOTUS Database
Bidens pilosaLOTUS Database
Blainvillea acmellaLOTUS Database
Boltonia asteroidesLOTUS Database
Brachystemma calycinumLOTUS Database
Brainea insignisLOTUS Database
Brassica napus var. napusFooDB
Brassica oleracea var. italicaFooDB
Brettanomyces anomalusLOTUS Database
Buddleja fallowianaLOTUS Database
Buddleja officinalisLOTUS Database
Bulbine frutescensLOTUS Database
Cajanus cajanLOTUS Database
Callicarpa integerrimaKNApSAcK Database
Calluna vulgarisLOTUS Database
Campanula persicifoliaLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Carduus tenuiflorusLOTUS Database
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Carthamus oxyacanthusLOTUS Database
Casearia membranaceaKNApSAcK Database
Cassia fistulaLOTUS Database
Castanea sativaLOTUS Database
Casuarina equisetifoliaLOTUS Database
Catharanthus roseusKNApSAcK Database
Centaurea collinaLOTUS Database
Centaurea regiaLOTUS Database
Centaurea scopariaLOTUS Database
Ceratostigma willmottianumKNApSAcK Database
Cestrum parquiLOTUS Database
Chamomilla rectitaPlant
Chenopodium albumFooDB
Chromolaena odorataLOTUS Database
Chrysanthemum coronariumLOTUS Database
Cichorium intybusKNApSAcK Database
Cinnamomum kotoenseLOTUS Database
Cinnamomum philippinenseKNApSAcK Database
Cinnamomum subaveniumPlant
Cinnamomum subavenium MIQ.KNApSAcK Database
Citrullus colocynthisPlant
Citrus paradisiFooDB
Citrus sinensisLOTUS Database
Citrus sudachiKNApSAcK Database
Cleidion spiciflorum (Burm. f.) Merr.KNApSAcK Database
Clematis ternifloraLOTUS Database
Cocos nuciferaFooDB
Codiaeum variegatumLOTUS Database
Codonopsis pilosulaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colchicum bornmuelleri FreynLOTUS Database
Colchicum soboliferumLOTUS Database
Colubrina faralaotra subsp.trichocarpa.KNApSAcK Database
Corchorus capsularisLOTUS Database
Coriandrum sativum L.FooDB
Crocus sativusKNApSAcK Database
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaFooDB
Cyclocarya paliurusLOTUS Database
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cyperus rotundusPlant
Cyperus rotundus L.KNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Derris scandensKNApSAcK Database
Dichroa febrifugaLOTUS Database
Dicliptera ripariaKNApSAcK Database
Diospyros lotusLOTUS Database
Diospyros maritimaLOTUS Database
Dipsacus asperKNApSAcK Database
Dipsacus inermisLOTUS Database
Drimia altissimaLOTUS Database
Drimia elataLOTUS Database
Duhaldea cappaLOTUS Database
Echinacea angustifoliaLOTUS Database
Elaeagnus pungensKNApSAcK Database
Elettaria cardamomumFooDB
Eleusine coracanaLOTUS Database
Eleutherococcus senticosusLOTUS Database
Elsholtzia bodinieriLOTUS Database
Engelhardia roxburghianaKNApSAcK Database
Entada phaseoloidesLOTUS Database
Ephedra equisetinaKNApSAcK Database
Equisetum arvenseLOTUS Database
Equsetum arvense-
Erica australisKNApSAcK Database
Erigeron canadensisLOTUS Database
Eriocaulon buergerianumKNApSAcK Database
Ervatamia coronariaLOTUS Database
Erythrina latissimaLOTUS Database
Euphorbia lagascaeLOTUS Database
Eurycoma longifoliaLOTUS Database
Fagara spp.KNApSAcK Database
Fagara tessmannii Engl.KNApSAcK Database
Fagopyrum esculentumFooDB
Falcaria vulgarisKNApSAcK Database
Festuca rubraLOTUS Database
Fibraurea tinctoriaLOTUS Database
Ficaria vernaLOTUS Database
Ficus caricaFooDB
Ficus erectaLOTUS Database
Ficus septicaKNApSAcK Database
Filipendula ulmariaLOTUS Database
Foeniculum vulgareFooDB
Forsythia suspensaLOTUS Database
Fragaria x ananassaFooDB
Galinsoga quadriradiataLOTUS Database
Gardenia carinataLOTUS Database
Gardenia sootepensisLOTUS Database
Gastrodia elataLOTUS Database
Gaultheria itoanaLOTUS Database
Gaultheria procumbensLOTUS Database
Ginkgo bilobaFooDB
Glehnia littoralisKNApSAcK Database
Gliricidia sepiumLOTUS Database
Glycine maxFooDB
Gomphrena celosioidesKNApSAcK Database
Gossypium hirsutumLOTUS Database
Gossypium mexicanumKNApSAcK Database
Goupia glabraLOTUS Database
Grindelia aphanactisKNApSAcK Database
Grosmannia crassivaginataLOTUS Database
Gymnadenia conopseaLOTUS Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Hagenia abyssinicaLOTUS Database
Halocharis hispidaLOTUS Database
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila engelmanniiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Haplophyllum cappadocicumLOTUS Database
Haplophyllum telephioidesLOTUS Database
Haplopteris anguste-elongataLOTUS Database
Hedysarum polybotrysLOTUS Database
Heptapleurum heptaphyllumLOTUS Database
Hibiscus taiwanensisKNApSAcK Database
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hornstedtia reticulataLOTUS Database
Houttuynia cordataLOTUS Database
Hovenia dulcisLOTUS Database
Humulus lupulusKNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Hyoscyamus nigerKNApSAcK Database
Hyssopus officinalis L.FooDB
Ilex pubescensLOTUS Database
Inonotus obliquusLOTUS Database
Iris ensataLOTUS Database
Iris germanicaLOTUS Database
Isatis tinctoriaLOTUS Database
Isodon japonicusLOTUS Database
Juglans nigra L.FooDB
Juncus effususLOTUS Database
Jurinea deltoideaLOTUS Database
Lagenaria brevifloraLOTUS Database
Lagerstroemia speciosaLOTUS Database
Lantana trifoliaLOTUS Database
Larix kaempferiLOTUS Database
Larix laricinaLOTUS Database
Larix sibiricaLOTUS Database
Lentinus edodes-
Lepisorus contortusLOTUS Database
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Lindera glaucaLOTUS Database
Liriodendron tulipiferaLOTUS Database
Litsea cubebaLOTUS Database
Lupinus angustifoliusLOTUS Database
Lycopus europaeusLOTUS Database
Maclura cochinchinensisLOTUS Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Magnolia salicifoliaLOTUS Database
Malus pumilaFooDB
Mangifera indicaKNApSAcK Database
Maranta arundinaceaFooDB
Matricaria chamomillaKNApSAcK Database
Matricaria recutitaFooDB
Matteuccia struthiopterisLOTUS Database
Medicago sativaKNApSAcK Database
Melia azedarachKNApSAcK Database
Melilotus messanensisKNApSAcK Database
Melissa officinalis L.FooDB
Mentha spicataFooDB
Menyanthes trifoliataLOTUS Database
Microtropis fokienensisKNApSAcK Database
Microtropis japonicaKNApSAcK Database
Millettia leucanthaLOTUS Database
Morella rubraLOTUS Database
Mucuna birdwoodianaLOTUS Database
Muntingia calaburaLOTUS Database
Musa x paradisiacaFooDB
Myriactis humilisLOTUS Database
Neopicrorhiza scrophulariiflora-
Notopterygium incisumKNApSAcK Database
Nymphaea albaLOTUS Database
Ocimum basilicumFooDB
Oenothera biennisLOTUS Database
Olea europaeaFooDB
Ophiocordyceps sinensisLOTUS Database
Opunitia dillenii HAW.-
Opuntia dilleniiKNApSAcK Database
Opuntia strictaLOTUS Database
Origanum majoranaFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza sativaFooDB
Oryza sativa cv. HeugjinjubyeoKNApSAcK Database
Oxalis corniculataKNApSAcK Database
Oxalis pes-capraeLOTUS Database
Paeonia hybridaKNApSAcK Database
Paeonia obovataLOTUS Database
Paeonia rockiiLOTUS Database
Paeonia tenuifoliaLOTUS Database
Panax ginsengKNApSAcK Database
Papaver somniferumLOTUS Database
Paratecoma koraiensisKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Peperomia blandaLOTUS Database
Peperomia duclouxii C. DC.KNApSAcK Database
Peperomia heyneanaLOTUS Database
Peperomia suiKNApSAcK Database
Peperomia tetraphyllaLOTUS Database
Periplaneta americanaLOTUS Database
Periploca nigrescensLOTUS Database
Persea americanaLOTUS Database
Persicaria lapathifoliaLOTUS Database
Petasites formosanusLOTUS Database
Petroselinum crispumFooDB
Phaseolus vulgarisLOTUS Database
Phellodendron amurenseLOTUS Database
Phellodendron amurense var.wilsoniiKNApSAcK Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phragmites australisLOTUS Database
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Picea ajanensisKNApSAcK Database
Picea glaucaLOTUS Database
Picea jezoensis var. jezoensisPlant
Picea koraiensisLOTUS Database
Picea obovataKNApSAcK Database
Picrorhiza kurrooaKNApSAcK Database
Picrorhiza kurrosaKNApSAcK Database
Picrorrhiza scrophulariaeflora-
Pimpinella anisumFooDB
Pinus edulisLOTUS Database
Pinus pinasterLOTUS Database
Pinus sibiricaKNApSAcK Database
Piper sarmentosumLOTUS Database
Pisum sativumFooDB
Planchonella vitiensisLOTUS Database
Plantago lanceolataKNApSAcK Database
Plantago majorKNApSAcK Database
Plantago mediaKNApSAcK Database
Pluchea argutaLOTUS Database
Polygonum capitatumLOTUS Database
Polygonum cognatumLOTUS Database
Polygonum convolvulusLOTUS Database
Polytrichum communeKNApSAcK Database
Populus deltoidesLOTUS Database
Populus euphraticaLOTUS Database
Populus lasiocarpaLOTUS Database
Populus pseudosimoniiKNApSAcK Database
Posidonia australisKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Premna fulvaLOTUS Database
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus cerasusFooDB
Prunus domesticaLOTUS Database
Prunus dulcisFooDB
Prunus japonicaLOTUS Database
Pseudolarix kaempferi Gord.KNApSAcK Database
Pterocarpus santalinusKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrrosia petiolosaLOTUS Database
Quercus ilexLOTUS Database
Quercus petraeaLOTUS Database
Quercus roburLOTUS Database
Quercus suberLOTUS Database
Ranunculus baudotiiKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rheum rhabarbarumFooDB
Rhinacanthus nasutusLOTUS Database
Rhodiola crenulataLOTUS Database
Rhododendron dauricumLOTUS Database
Rohdea chinensisPlant
Rorippa indicaLOTUS Database
Rorippa sylvestrisLOTUS Database
Rosa caninaKNApSAcK Database
Rubia yunnanensisKNApSAcK Database
Rubus idaeusFooDB
Rubus spectabilisFooDB
Rumex japonicusLOTUS Database
Salvia officinalisKNApSAcK Database
Salvia rosmarinusFooDB
Sambucus racemosaLOTUS Database
Santalum albumLOTUS Database
Saposhnikovia divaricataLOTUS Database
Sarcandra glabraLOTUS Database
Sarcolaeana multiflora-
Sargentodoxa cuneataLOTUS Database
Saussurea eriostemonLOTUS Database
Saussurea medusaLOTUS Database
Scapholeberis mucronataLOTUS Database
Scrophularia frutescensPlant
Scrophularia nodosaLOTUS Database
Scrophularis sambucifolia-
Secale cerealeFooDB
Secamone afzeliiLOTUS Database
Sesamum indicumFooDB
Sida acutaLOTUS Database
Silphium perfoliatumLOTUS Database
Simaba orinocensisLOTUS Database
Sinapis albaLOTUS Database
Siphoneugena densifloraLOTUS Database
Smilax chinaLOTUS Database
Solanum lycopersicum var. lycopersicumFooDB
Solanum lyratumLOTUS Database
Solanum tuberosumKNApSAcK Database
Solidago virgaureaLOTUS Database
Solori scandensPlant
Sorghum bicolorLOTUS Database
Sparganium eurycarpumLOTUS Database
Sparganium stoloniferumKNApSAcK Database
Spiraea formosanaKNApSAcK Database
Stellaria dichotomaLOTUS Database
Strobilanthes crispusPlant
Synsepalum dulcificumLOTUS Database
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Talipariti tiliaceumLOTUS Database
Taraxacum formosanumKNApSAcK Database
Taraxacum officinaleFooDB
Taxus baccataKNApSAcK Database
Taxus wallichianaLOTUS Database
Tecoma stansLOTUS Database
Terminalia catappaPlant
Terminalia chebulaPlant
Terminalia nigrovenulosaPlant
Tetracentron sinenseKNApSAcK Database
Teucrium divaricatumLOTUS Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Theobroma cacaoFooDB
Thymus vulgarisFooDB
Tinospora cordifoliaLOTUS Database
Toona ciliataKNApSAcK Database
Trachelospermum asiaticumKNApSAcK Database
Trachelospermum jasminoidesLOTUS Database
Tribulus terrestrisPlant
Trichosanthes cucumeroidesLOTUS Database
Trichosanthes kirilowiiKNApSAcK Database
Trifolium pratensePlant
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum turgidumLOTUS Database
Tupistra chinensisKNApSAcK Database
Vaccinium angustifoliumLOTUS Database
Vaccinium corymbosumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
VanillaFooDB
Vanilla planifolia Jacks.LOTUS Database
Veronica peregrina L.KNApSAcK Database
Veronica persicaLOTUS Database
Viscum coloratumKNApSAcK Database
Visnea mocaneraLOTUS Database
Vitex agnus-castusLOTUS Database
Vitex rotundifoliaLOTUS Database
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Vittaria anguste-elongataKNApSAcK Database
Withania somniferaPlant
Wurmbea dioicaLOTUS Database
Xanthium strumariumLOTUS Database
Zanthoxylum ailanthoidesLOTUS Database
Zanthoxylum beecheyanumLOTUS Database
Zanthoxylum gilletiiLOTUS Database
Zanthoxylum leprieuriiLOTUS Database
Zanthoxylum simulansKNApSAcK Database
Zea maysLOTUS Database
Zea mays L.KNApSAcK Database
Zingiber montanumLOTUS Database
Zingiber officinaleFooDB
Zostera marinaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas pseudoalcaligenesKNApSAcK Database
Streptomyces sp. GW23/1540KNApSAcK Database
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
  • M-methoxybenzoic acid or derivatives
    • 

  • Hydroxybenzoic acid
    • 

  • Methoxyphenol
    • 

  • Benzoic acid
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Benzoyl
    • 

  • Phenol ether
    • 

  • Methoxybenzene
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °Chttps://en.wikipedia.org/wiki/Vanillic_acid
Boiling Point353.43 °C. @  760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.5 mg/mL at 14 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP1.43Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility5.7 g/LALOGPS
logP1.7ALOGPS
logP1.17ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000484  
DrugBank IDNot Available
Phenol Explorer Compound ID414  
FoodDB IDFDB000846  
KNApSAcK IDC00002682  
Chemspider ID8155  
KEGG Compound IDC06672  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVanillic acid  
METLIN ID5471  
PubChem Compound8468  
PDB IDNot Available
ChEBI ID30816  
Good Scents IDrw1051611  
References
General References
  1. Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649  ] 
  2. Ebinger G, Verheyden R: On the occurence of vanillic acid in human brain and cerebrospinal fluid. J Neurol. 1976 Apr 23;212(2):133-8. [PubMed:57225  ] 
  3. Lee BL, New AL, Kok PW, Ong HY, Shi CY, Ong CN: Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure. Clin Chem. 1993 Sep;39(9):1788-92. [PubMed:8375048  ] 
  4. 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  ] 
  5. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241  ]