NP-MRD: Showing NP-Card for [(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid (NP0227932)

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Record Information

Version

2.0

Created at

2022-09-06 07:25:01 UTC

Updated at

2022-09-06 07:25:01 UTC

NP-MRD ID

NP0227932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

Description

Norbadione A belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. [(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid is found in Chalciporus piperatus, Pisolithus arhizus and Xerocomus badius. [(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid was first documented in 2009 (PMID: 19890513). Based on a literature review a small amount of articles have been published on Norbadione A (PMID: 26474393) (PMID: 25813231) (PMID: 20831226) (PMID: 19309153).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209252D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062209252D          

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    0.2578   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -1.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    0.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749    1.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    2.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629    2.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517    3.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    2.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7006    3.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3138    4.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515    5.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5760    4.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137    5.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628    4.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251    3.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    2.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6092    1.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    0.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377   -2.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -2.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278   -3.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
 31 43  1  0  0  0  0
 43 44  1  0  0  0  0
 28 44  1  0  0  0  0
 44 45  2  0  0  0  0
 27 46  1  0  0  0  0
 22 46  1  0  0  0  0
 46 47  2  0  0  0  0
 19 47  1  0  0  0  0
 23 48  1  0  0  0  0
 48 49  1  0  0  0  0
 21 49  1  0  0  0  0
 49 50  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0227932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=C1\OC(=O)C(=C1O)C1=CC2=C3C(OC2=O)=C(O)C=C(C2=C(O)\C(OC2=O)=C(/C(O)=O)C2=CC=C(O)C=C2)C3=C1)\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22+,30-23+

> <INCHI_KEY>
NEAFOYGNZAYARY-KBWMUOTDSA-N

> <FORMULA>
C35H18O15

> <MOLECULAR_WEIGHT>
678.514

> <EXACT_MASS>
678.06456988

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
65.44697289248919

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-4-{9-[(5E)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4,6,8(12),9-pentaen-6-yl}-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

> <JCHEM_LOGP>
3.940301529

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.7476393574324143

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1455645457617494

> <JCHEM_PKA_STRONGEST_BASIC>
-4.400536940547782

> <JCHEM_POLAR_SURFACE_AREA>
254.64999999999992

> <JCHEM_REFRACTIVITY>
170.3242000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2E)-4-{9-[(5E)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4,6,8(12),9-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -3.988  -2.555   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.827  -1.024   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.972   0.007   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.345   1.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.115   2.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.345   4.081   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.115   5.415   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.805   4.081   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.655   2.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.425   1.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.965   1.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.735   2.747   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -11.275   2.747   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.965   4.081   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.425   4.081   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.814   1.253   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.783   2.397   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.494  -0.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.087  -0.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.926  -2.412   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.481  -3.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.727  -2.133   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.973  -3.038   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.380  -2.412   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.626  -3.317   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.541  -0.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.295   0.025   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.510   1.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.403   2.621   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.887   2.354   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.079   4.004   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.357   5.365   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.818   5.419   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.096   6.780   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.001   4.114   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.174   6.670   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.452   8.030   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.269   9.336   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.809   9.281   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.626  10.586   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.531   7.920   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.713   6.615   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.604   3.789   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.871   2.272   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.254   1.596   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.566  -0.601   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.159   0.025   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.497  -4.503   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.957  -4.503   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       0.052  -5.748   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18   20   47                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   49                                                  
CONECT   22   21   23   46                                                  
CONECT   23   22   24   48                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   46                                                  
CONECT   28   27   29   44                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   43                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
CONECT   43   31   44                                                       
CONECT   44   43   28   45                                                  
CONECT   45   44                                                            
CONECT   46   27   22   47                                                  
CONECT   47   46   19                                                       
CONECT   48   23   49                                                       
CONECT   49   48   21   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₁₈O₁₅

Average Mass

678.5140 Da

Monoisotopic Mass

678.06457 Da

IUPAC Name

2-[(2E)-4-{9-[(5E)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4,6,8(12),9-pentaen-6-yl}-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

Traditional Name

[(2E)-4-{9-[(5E)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4,6,8(12),9-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(=C1\OC(=O)C(=C1O)C1=CC2=C3C(OC2=O)=C(O)C=C(C2=C(O)\C(OC2=O)=C(/C(O)=O)C2=CC=C(O)C=C2)C3=C1)\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22+,30-23+

InChI Key

NEAFOYGNZAYARY-KBWMUOTDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chalciporus piperatus	LOTUS Database	35616633
Pisolithus arhizus	LOTUS Database	35616633
Xerocomus badius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
2-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
2-furanone
Benzenoid
Dihydrofuran
Enol ester
Vinylogous acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Enol
Carboxylic acid
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.94	ChemAxon
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	254.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	170.32 m³·mol⁻¹	ChemAxon
Polarizability	65.45 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28284768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norbadione A

METLIN ID

Not Available

PubChem Compound

54679293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Martincic R, Mravljak J, Svajger U, Perdih A, Anderluh M, Novic M: In Silico Discovery of Novel Potent Antioxidants on the Basis of Pulvinic Acid and Coumarine Derivatives and Their Experimental Evaluation. PLoS One. 2015 Oct 16;10(10):e0140602. doi: 10.1371/journal.pone.0140602. eCollection 2015. [PubMed:26474393 ]
Martincic R, Kuzmanovski I, Wagner A, Novic M: Development of models for prediction of the antioxidant activity of derivatives of natural compounds. Anal Chim Acta. 2015 Apr 8;868:23-35. doi: 10.1016/j.aca.2015.01.050. Epub 2015 Feb 7. [PubMed:25813231 ]
Korovitch A, Mulon JB, Souchon V, Leray I, Valeur B, Mallinger A, Nadal B, Le Gall T, Lion C, Ha-Duong NT, El Hage Chahine JM: Norbadione a: kinetics and thermodynamics of cesium uptake in aqueous and alcoholic media. J Phys Chem B. 2010 Oct 7;114(39):12655-65. doi: 10.1021/jp1060232. [PubMed:20831226 ]
Kuad P, Schurhammer R, Maechling C, Antheaume C, Mioskowski C, Wipff G, Spiess B: Complexation of Cs+, K+ and Na+ by norbadione A triggered by the release of a strong hydrogen bond: nature and stability of the complexes. Phys Chem Chem Phys. 2009 Nov 28;11(44):10299-310. doi: 10.1039/b912518c. Epub 2009 Sep 23. [PubMed:19890513 ]
Habrant D, Poigny S, Segur-Derai M, Brunel Y, Heurtaux B, Le Gall T, Strehle A, Saladin R, Meunier S, Mioskowski C, Wagner A: Evaluation of antioxidant properties of monoaromatic derivatives of pulvinic acids. J Med Chem. 2009 Apr 23;52(8):2454-64. doi: 10.1021/jm801500h. [PubMed:19309153 ]
LOTUS database [Link]

Showing NP-Card for [(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid (NP0227932)

MOL for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D MOL for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D SDF for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D-SDF for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

PDB for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D PDB for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

SMILES for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

INCHI for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

Structure for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D Structure for NP0227932 ([(2e)-4-{9-[(5e)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),4,6,8,10-pentaen-6-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)