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Showing NP-Card for 7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid (NP0278217)

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Record Information
Version2.0
Created at2022-09-09 03:10:07 UTC
Updated at2022-09-09 03:10:07 UTC
NP-MRD IDNP0278217
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid
DescriptionConvolvulanic acid B, also known as convolvulanate b, belongs to the class of organic compounds known as m-phthalic acid and derivatives. These are aromatic compounds containing a benzene ring bearing a carboxylic acid group at ring carbon atoms 1 and 2. 7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid is found in Diaporthe convolvuli. Convolvulanic acid B is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)


  Mrv1533004151518412D          

 16 17  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  3 16  1  0  0  0  0
 11 16  2  0  0  0  0
M  END
Download

3D MOL for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.2631    0.6741   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.6085    0.9241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    0.2049    0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -1.1149    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -2.1206    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -1.5058    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598   -0.5391   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9122   -0.8912   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011    0.0236   -0.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2930   -2.2351   -0.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1678    0.7829   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    1.1774    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1957    2.6345    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1886    3.3331    0.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0436    3.0435   -0.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9323    1.9901   -0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8803    1.2723   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645   -0.3704   -0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082    1.0838    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -1.6872    1.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643   -3.0036    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -2.4326    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -2.5527    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2754   -2.4220   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    1.9259   -1.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931    2.1205    0.1188 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12  3  1  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
 10 24  1  0
 16 25  1  0
 16 26  1  0
M  END
Download

3D SDF for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)


  Mrv1533004151518412D          

 16 17  0  0  0  0            999 V2000
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  3 16  1  0  0  0  0
 11 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C=C(C(O)=O)C2=C1C(=O)OC2

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O5/c1-5-3-6(10(12)13)7-4-16-11(14)8(7)9(5)15-2/h3H,4H2,1-2H3,(H,12,13)

> <INCHI_KEY>
LEHYHKDJJLQWJA-UHFFFAOYSA-N

> <FORMULA>
C11H10O5

> <MOLECULAR_WEIGHT>
222.196

> <EXACT_MASS>
222.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.110551971594916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylic acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.541283113

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.593767915353581

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7989322042773765

> <JCHEM_PKA_STRONGEST_BASIC>
-4.908061421076649

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
55.39850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-6-methyl-1-oxo-3H-2-benzofuran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)

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PDB for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)
HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.787  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    3   11                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)
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SMILES for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)
COC1=C(C)C=C(C(O)=O)C2=C1C(=O)OC2
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INCHI for NP0278217 (7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carboxylic acid)
InChI=1S/C11H10O5/c1-5-3-6(10(12)13)7-4-16-11(14)8(7)9(5)15-2/h3H,4H2,1-2H3,(H,12,13)
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View in JSmol
Synonyms
ValueSource
Convolvulanate bGenerator
7-Methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylateGenerator
Chemical FormulaC11H10O5
Average Mass222.1960 Da
Monoisotopic Mass222.05282 Da
IUPAC Name7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylic acid
Traditional Name7-methoxy-6-methyl-1-oxo-3H-2-benzofuran-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(C)C=C(C(O)=O)C2=C1C(=O)OC2
InChI Identifier
InChI=1S/C11H10O5/c1-5-3-6(10(12)13)7-4-16-11(14)8(7)9(5)15-2/h3H,4H2,1-2H3,(H,12,13)
InChI KeyLEHYHKDJJLQWJA-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
Diaporthe convolvuliLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-phthalic acid and derivatives. These are aromatic compounds containing a benzene ring bearing a carboxylic acid group at ring carbon atoms 1 and 2.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentM-phthalic acid and derivatives  
Alternative Parents
Substituents
  • Meta_phthalic_acid
    • 

  • P-methoxybenzoic acid or derivatives
    • 

  • Isobenzofuranone
    • 

  • Phthalide
    • 

  • Isocoumaran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.22ALOGPS
logP1.54ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.4 m³·mol⁻¹ChemAxon
Polarizability21.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
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 Compound3083579  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]