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Showing NP-Card for 5-hydroxy-2-methoxybenzoic acid (NP0205553)

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Record Information
Version2.0
Created at2022-09-05 01:29:20 UTC
Updated at2022-09-05 01:29:21 UTC
NP-MRD IDNP0205553
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-2-methoxybenzoic acid
Description5-Hydroxy-2-methoxybenzoic acid belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. 5-hydroxy-2-methoxybenzoic acid is found in Penicillium oxalicum and Vitex agnus-castus. 5-Hydroxy-2-methoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0205553 (5-hydroxy-2-methoxybenzoic acid)


  Mrv1652310081718592D          

 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
    1.4289   -0.0000    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
    0.0000   -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
    0.0000    0.8250    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
   -0.7145    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
Download

3D MOL for NP0205553 (5-hydroxy-2-methoxybenzoic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.8673   -0.9994   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    0.0996   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301   -0.1294   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690   -1.4154   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836   -1.6419    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -0.5962    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4411   -0.9091    0.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057    0.6757   -0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.9190   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    2.2874   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    2.4703   -0.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    3.3157   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -1.3531    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715   -0.6160   -0.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009   -1.8001   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8646   -2.2769   -0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -2.6815    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168   -0.9525    1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    1.4802   -0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6552    4.1237    0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  4  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  8 19  1  0
  7 18  1  0
  5 17  1  0
  4 16  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0205553 (5-hydroxy-2-methoxybenzoic acid)


  Mrv1652310081718592D          

 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
    1.4289   -0.0000    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
    0.0000   -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
    0.0000    0.8250    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
   -0.7145    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C(O)C=C1)C(O)=O

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

> <INCHI_KEY>
FXMQSVMVTHLCSF-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.762052059014566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.1695921366666666

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.988729634970632

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.466153281529346

> <JCHEM_PKA_STRONGEST_BASIC>
-4.875952786113643

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
41.7583

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-methoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0205553 (5-hydroxy-2-methoxybenzoic acid)

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PDB for NP0205553 (5-hydroxy-2-methoxybenzoic acid)
HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   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  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    5    6                                                       
CONECT    5    2    4    9                                                  
CONECT    6    4    7    8                                                  
CONECT    7    3    6   12                                                  
CONECT    8    6   10   11                                                  
CONECT    9    5                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    1    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0205553 (5-hydroxy-2-methoxybenzoic acid)
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SMILES for NP0205553 (5-hydroxy-2-methoxybenzoic acid)
COC1=C(C=C(O)C=C1)C(O)=O
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INCHI for NP0205553 (5-hydroxy-2-methoxybenzoic acid)
InChI=1S/C8H8O4/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
5-Hydroxy-2-methoxybenzoateGenerator
Chemical FormulaC8H8O4
Average Mass168.1480 Da
Monoisotopic Mass168.04226 Da
IUPAC Name5-hydroxy-2-methoxybenzoic acid
Traditional Name5-hydroxy-2-methoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=C(C=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-3-2-5(9)4-6(7)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyFXMQSVMVTHLCSF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Penicillium oxalicumLOTUS Database
Vitex agnus-castusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentO-methoxybenzoic acids and derivatives  
Alternative Parents
Substituents
  • O-methoxybenzoic acid or derivatives
    • 

  • Methoxyphenol
    • 

  • Hydroxybenzoic acid
    • 

  • 4-alkoxyphenol
    • 

  • Benzoic acid
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Benzoyl
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.76ALOGPS
logP1.17ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
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
Polarizability15.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0166110  
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 Compound18464607  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]