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Showing NP-Card for 3,5-dimethoxybenzoic acid (NP0265297)

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Record Information
Version2.0
Created at2022-09-08 09:13:44 UTC
Updated at2022-09-08 09:13:44 UTC
NP-MRD IDNP0265297
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-dimethoxybenzoic acid
Description3,5-Dimethoxybenzoic acid 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. 3,5-dimethoxybenzoic acid is found in Calophyllum polyanthum and Melia azedarach. 3,5-dimethoxybenzoic acid was first documented in 2004 (PMID: 15387670). 3,5-Dimethoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 19708767).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0265297 (3,5-dimethoxybenzoic acid)


  Mrv1652308201916452D          

 13 13  0  0  0  0            999 V2000
    2.8579    0.0000    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
    1.4289    0.8250    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   -0.4125    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
    1.4289    0.0000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
M  END
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3D MOL for NP0265297 (3,5-dimethoxybenzoic acid)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -0.3814    3.3276   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987    2.4615   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119    1.0790   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160    0.4912    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7416   -0.9000    0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -1.4822    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1171   -0.6511    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966   -1.6638   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6491   -1.1063   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -1.9220   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9348   -1.3525   -0.5909 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7777   -3.2916   -0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6988    0.2703   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2849    2.9906   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504    3.5436    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978    4.3025   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006    1.0985    0.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519   -0.2266   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962   -1.2634    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463    0.1360    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -2.7600    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0527   -3.8470    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    0.7656   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13  9  1  0
  9  8  2  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  5  4  2  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  4  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
 13 23  1  0
  8 21  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
  4 17  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0265297 (3,5-dimethoxybenzoic acid)


  Mrv1652308201916452D          

 13 13  0  0  0  0            999 V2000
    2.8579    0.0000    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
    1.4289    0.8250    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   -0.4125    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
    1.4289    0.0000    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265297

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
IWPZKOJSYQZABD-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.175

> <EXACT_MASS>
182.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.980352286855666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dimethoxybenzoic acid

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.315486192666666

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6038221221840394

> <JCHEM_PKA_STRONGEST_BASIC>
-4.545095975195607

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
46.24060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dimethoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0265297 (3,5-dimethoxybenzoic acid)

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PDB for NP0265297 (3,5-dimethoxybenzoic acid)
HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   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   1.540   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    3    4    9                                                  
CONECT    7    3    5   12                                                  
CONECT    8    4    5   13                                                  
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1    7                                                       
CONECT   13    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0265297 (3,5-dimethoxybenzoic acid)
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SMILES for NP0265297 (3,5-dimethoxybenzoic acid)
COC1=CC(=CC(OC)=C1)C(O)=O
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INCHI for NP0265297 (3,5-dimethoxybenzoic acid)
InChI=1S/C9H10O4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5H,1-2H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
3,5-DimethoxybenzoateGenerator
35-Dimethoxybenzoic acidChEMBL, HMDB
35-DimethoxybenzoateGenerator, HMDB
Chemical FormulaC9H10O4
Average Mass182.1750 Da
Monoisotopic Mass182.05791 Da
IUPAC Name3,5-dimethoxybenzoic acid
Traditional Name3,5-dimethoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5H,1-2H3,(H,10,11)
InChI KeyIWPZKOJSYQZABD-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
Calophyllum polyanthumLOTUS Database
Melia azedarachLOTUS 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
    • 

  • Dimethoxybenzene
    • 

  • M-dimethoxybenzene
    • 

  • Benzoic acid
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Benzoyl
    • 

  • Phenol ether
    • 

  • Methoxybenzene
    • 

  • Alkyl aryl ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.43ALOGPS
logP1.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.24 m³·mol⁻¹ChemAxon
Polarizability17.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0127495  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB086357  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID142601  
Good Scents IDNot Available
References
General References
  1. Ma CH, Chen B, Qi HY, Li BG, Zhang GL: Two pyranocoumarins from the seeds of Calophyllum polyanthum. J Nat Prod. 2004 Sep;67(9):1598-600. doi: 10.1021/np0499158. [PubMed:15387670  ] 
  2. Khan AN, Perveen S, Malik A, Afza N, Iqbal L, Latif M, Saleem M: Conferin, potent antioxidant and anti-inflammatory isoflavone from Caragana conferta Benth. J Enzyme Inhib Med Chem. 2010 Jun;25(3):440-4. doi: 10.1080/14756360903179484. [PubMed:19708767  ] 
  3. LOTUS database [Link]