Np mrd loader

Showing NP-Card for 2-Hydroxy-3-methoxybenzoic acid (NP0047798)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 20:46:09 UTC
Updated at2022-03-17 20:46:09 UTC
NP-MRD IDNP0047798
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxy-3-methoxybenzoic acid
Description3-Methoxysalicylic acid, also known as O-vanillic acid or O-vanillate, 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. 3-Methoxysalicylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-Methoxysalicylic acid has been detected, but not quantified in, evening primroses. This could make 3-methoxysalicylic acid a potential biomarker for the consumption of these foods. 2-Hydroxy-3-methoxybenzoic acid is found in Betula pendula, Colchicum decaisnei, Gentiana scabra and Salvia divaricata. 3-Methoxysalicylic acid (CAS Number 877-22-5) is a beige fine crystalline powder.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)


  Mrv0541 02241220002D          

 12 12  0  0  0  0            999 V2000
   -0.0417    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    1.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448   -0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    0.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -1.8576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -0.6190    0.0000 O   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
  3  8  1  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  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)

Download
3D SDF for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)

  Mrv0541 02241220002D          

 12 12  0  0  0  0            999 V2000
   -0.0417    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    1.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448   -0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    0.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -1.8576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -1.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -0.6190    0.0000 O   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
  3  8  1  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  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047798

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
AUZQQIPZESHNMG-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.729063203787003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.8195921366666663

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.589185949007934

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5535481957657793

> <JCHEM_PKA_STRONGEST_BASIC>
-4.900310338326878

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
41.758300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxysalicyclic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)
Download
PDB for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.078   3.468   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.309   2.697   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.309   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.697   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.697  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.309  -1.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.078  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.078   0.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.309   1.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.309  -3.468   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.309  -1.926   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.697  -1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)
Download
SMILES for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)
COC1=CC=CC(C(O)=O)=C1O
Download
INCHI for NP0047798 (2-Hydroxy-3-methoxybenzoic acid)
InChI=1S/C8H8O4/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4,9H,1H3,(H,10,11)
Download
View in JSmol
Synonyms
ValueSource
O-Vanillic acidChEBI
O-VanillateGenerator
3-MethoxysalicylateGenerator
2-Hydroxy-3-methoxybenzoic acidHMDB
2-Hydroxy-3-methoxybenzoateGenerator
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-hydroxy-3-methoxybenzoic acid
Traditional Name3-methoxysalicyclic acid
CAS Registry Number877-22-5
SMILES
COC1=CC=CC(C(O)=O)=C1O
InChI Identifier
InChI=1S/C8H8O4/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyAUZQQIPZESHNMG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Betula pendulaLOTUS Database
Colchicum decaisneiPlant
Gentiana scabraLOTUS Database
Oenothera biennisFooDB
Salvia divaricataLOTUS 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
    • 

  • Salicylic acid
    • 

  • Salicylic acid or derivatives
    • 

  • Hydroxybenzoic acid
    • 

  • Methoxyphenol
    • 

  • Benzoic acid
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.87ALOGPS
logP1.82ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
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
Polarizability15.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059713  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012172  
KNApSAcK IDNot Available
Chemspider ID63328  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70140  
PDB IDNot Available
ChEBI ID68496  
Good Scents IDNot Available
References
General References