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Showing NP-Card for 3-hydroxy-4-methoxybenzoicacid (NP0331805)

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Record Information
Version2.0
Created at2023-09-08 08:26:10 UTC
Updated at2024-09-03 04:17:00 UTC
NP-MRD IDNP0331805
Natural Product DOIhttps://doi.org/10.57994/0892
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-hydroxy-4-methoxybenzoicacid
DescriptionIsovanillic acid, also known as acide isovanillique or 3-hydroxy-p-anisate, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. Isovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a selective inhibitor of aldehyde oxidase. Isovanillic acid is a metabolite of isovanillin. Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. 3-hydroxy-4-methoxybenzoicacid was first documented in 2012 (PMID: 23477143). It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid (PMID: 24956816) (PMID: 24820992).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0331805 (3-hydroxy-4-methoxybenzoicacid)


  Mrv0541 04091314192D          

 12 12  0  0  0  0            999 V2000
    6.2464    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    2.1804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    3.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
Download

3D MOL for NP0331805 (3-hydroxy-4-methoxybenzoicacid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.3558    0.5496   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665   -0.0833    0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -0.0723    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5540    0.5391   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    0.5338   -1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775   -0.0760   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -0.0891   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562    0.4811   -1.5174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488   -0.7215    0.4238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.6929    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091   -0.6797    1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -1.3055    2.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.0562   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9452    1.5886   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.5759   -0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523    1.0162   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149    1.0150   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5878   -0.1179    0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567   -1.1644    1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6656   -1.3531    2.4681 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 10  1  0
 10 11  2  0
 11 12  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
 10 19  1  0
 12 20  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0331805 (3-hydroxy-4-methoxybenzoicacid)


  Mrv0541 04091314192D          

 12 12  0  0  0  0            999 V2000
    6.2464    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    2.1804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    3.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331805

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
LBKFGYZQBSGRHY-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.894359785080015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.1695921366666666

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.958072873488197

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.147477192001137

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911668652620585

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
41.758300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0331805 (3-hydroxy-4-methoxybenzoicacid)

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PDB for NP0331805 (3-hydroxy-4-methoxybenzoicacid)
HEADER    PROTEIN                                 09-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-13         0                                  
HETATM    1  C   UNK     0      11.660   7.150   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.326   6.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.326   4.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.660   4.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.994   4.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.994   6.380   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.327   7.150   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.993   4.070   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      11.660   2.530   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.327   8.690   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.661   6.380   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.993   2.530   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6   10   11                                                  
CONECT    8    3   12                                                       
CONECT    9    4                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0331805 (3-hydroxy-4-methoxybenzoicacid)
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SMILES for NP0331805 (3-hydroxy-4-methoxybenzoicacid)
COC1=CC=C(C=C1O)C(O)=O
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INCHI for NP0331805 (3-hydroxy-4-methoxybenzoicacid)
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
3-Hydroxy-p-anisic acidChEBI
3-Hydroxyanisic acidChEBI
Acide isovanilliqueChEBI
3-Hydroxy-p-anisateGenerator
3-HydroxyanisateGenerator
IsovanillateGenerator
3-Hydroxy-4-methoxybenzoateHMDB
Isovanillic acidChEBI
3-Hydroxy-4-methoxybenzoic acid
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name3-hydroxy-4-methoxybenzoic acid
Traditional Nameisovanillic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
InChI KeyLBKFGYZQBSGRHY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentP-methoxybenzoic acids and derivatives  
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
    • 

  • Hydroxybenzoic acid
    • 

  • Methoxyphenol
    • 

  • Benzoic acid
    • 

  • Phenoxy compound
    • 

  • Benzoyl
    • 

  • Phenol ether
    • 

  • Methoxybenzene
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid derivative
    • 

  • 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
logP1.81ALOGPS
logP1.17ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
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
Polarizability15.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060003  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12575  
PDB IDNot Available
ChEBI ID63798  
Good Scents IDNot Available
References
General References
  1. Wang L, Gong XJ, Zhou X, Xian C, Yang SL, Yang ZN: [Chemical constituents of Psammosilene tunicoides and bacteriostatic activity]. Zhongguo Zhong Yao Za Zhi. 2012 Dec;37(23):3577-80. [PubMed:23477143  ] 
  2. Jiang YP, Li H, Pan XZ, Sun XG, Tang QF, Shao M: [Chemical constituents from the roots of Ilex pubescens]. Zhong Yao Cai. 2013 Nov;36(11):1774-8. [PubMed:24956816  ] 
  3. Zhang J, Yan LT, Yuan EL, Ding HX, Ye HC, Zhang ZK, Yan C, Liu YQ, Feng G: Antifungal activity of compounds extracted from Cortex Pseudolaricis against Colletotrichum gloeosporioides. J Agric Food Chem. 2014 May 28;62(21):4905-10. doi: 10.1021/jf500968b. Epub 2014  May 19. [PubMed:24820992  ]