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Showing NP-Card for 3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde (NP0326502)

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Record Information
Version2.0
Created at2022-09-12 08:06:46 UTC
Updated at2022-09-12 08:06:46 UTC
NP-MRD IDNP0326502
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde
Description3,5-Dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. 3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde is found in Aspergillus duricaulis, Lepteutypa cupressi, Penicillium commune and Seiridium cupressi. 3,5-Dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)


  Mrv1533004231521582D          

 17 18  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
    4.7079   -0.4125    0.0000 O   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    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
    1.5249   -1.0396    0.0000 O   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  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 11 17  2  0  0  0  0
M  END
Download

3D MOL for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -3.0861   -1.1020   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181   -0.5697    0.9723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.1266    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388    1.1729    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0137    2.0769    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786    1.6471   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431    2.9620   -0.6574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    0.7641   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594    1.2570   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7436    0.4883   -0.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319   -0.5491    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951   -1.0262    0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2384   -2.4276    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6566   -3.1891    1.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -2.7830    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -1.6696    0.1871 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8385   -1.9613   -1.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9943   -0.4807   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691   -2.1177    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.2834   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857    2.5888   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164    2.8616    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9115    1.5354    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676    3.5641   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074    2.2757   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -1.4817    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -2.4263   -0.9732 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 12  3  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  9 25  1  0
 16 26  1  1
 17 27  1  0
M  END
Download

3D SDF for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)


  Mrv1533004231521582D          

 17 18  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
    4.7079   -0.4125    0.0000 O   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    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
    1.5249   -1.0396    0.0000 O   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  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 11 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0326502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(O)=C(C=O)C2=C1C(=O)OC2O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O6/c1-4-8(13)5(3-12)6-7(9(4)16-2)11(15)17-10(6)14/h3,10,13-14H,1-2H3

> <INCHI_KEY>
BHVGIMSTMICYNZ-UHFFFAOYSA-N

> <FORMULA>
C11H10O6

> <MOLECULAR_WEIGHT>
238.195

> <EXACT_MASS>
238.047738042

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.95604911249062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
1.5784132863333333

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.11518809282771

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.665978910519515

> <JCHEM_PKA_STRONGEST_BASIC>
-4.566755520221315

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
57.737100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3H-2-benzofuran-4-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)

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PDB for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-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  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.454  -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       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   17  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   17                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3   11                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)
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SMILES for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)
COC1=C(C)C(O)=C(C=O)C2=C1C(=O)OC2O
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INCHI for NP0326502 (3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde)
InChI=1S/C11H10O6/c1-4-8(13)5(3-12)6-7(9(4)16-2)11(15)17-10(6)14/h3,10,13-14H,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H10O6
Average Mass238.1950 Da
Monoisotopic Mass238.04774 Da
IUPAC Name3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde
Traditional Name3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3H-2-benzofuran-4-carbaldehyde
CAS Registry NumberNot Available
SMILES
COC1=C(C)C(O)=C(C=O)C2=C1C(=O)OC2O
InChI Identifier
InChI=1S/C11H10O6/c1-4-8(13)5(3-12)6-7(9(4)16-2)11(15)17-10(6)14/h3,10,13-14H,1-2H3
InChI KeyBHVGIMSTMICYNZ-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
Aspergillus duricaulisLOTUS Database
Lepteutypa cupressiLOTUS Database
Penicillium communeLOTUS Database
Seiridium cupressiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassBenzofuranones  
Direct ParentBenzofuranones  
Alternative Parents
Substituents
  • Isobenzofuranone
    • 

  • Benzofuranone
    • 

  • Phthalide
    • 

  • Isocoumaran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Aryl-aldehyde
    • 

  • Benzenoid
    • 

  • Vinylogous acid
    • 

  • Carboxylic acid ester
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Aldehyde
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • 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
logP0.33ALOGPS
logP1.58ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.74 m³·mol⁻¹ChemAxon
Polarizability21.96 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 Compound119395  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]