NP-MRD: Showing NP-Card for [3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid (NP0206693)

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Record Information

Version

1.0

Created at

2022-09-05 03:01:58 UTC

Updated at

2022-09-05 03:01:58 UTC

NP-MRD ID

NP0206693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

Description

2-[3-Hydroxy-4-(6-methoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). [3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid is found in Xerocomus badius. 2-[3-Hydroxy-4-(6-methoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516422D          

 32 35  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
    0.0000   -1.6500    0.0000 O   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   -0.4125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7600    1.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5156    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361    1.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    2.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8210    1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    2.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    2.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253    2.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0608    3.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    4.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813    3.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3662    3.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925    0.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -1.1425    0.0000 O   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
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    8.5655   -0.2110   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6958    0.0076    1.0804 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3265    0.0843    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    0.4909    2.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    0.6061    2.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735    0.9887    3.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    0.2822    0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244    0.3843    0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150    0.0653   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361    0.1099   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830   -0.3033    0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -0.8370    1.7506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393   -0.0936    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5226   -0.3284    0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -0.9016    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -1.2702    2.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662   -1.0975    2.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7297   -0.0141   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8060   -0.3503   -1.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9068   -0.0568   -2.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9932    0.6004   -1.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1185    0.8998   -2.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9304    0.9393   -0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8225    0.6396    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    0.4867   -1.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    0.6135   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    1.0937   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.3540   -1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4137   -0.4501   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031   -0.1314   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661   -0.2383   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1699   -0.6202   -1.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2860   -1.1922   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4478    0.6336   -0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6010   -0.2179    0.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519    0.7512    2.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    0.7236    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609   -0.3366    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3928   -0.7632    3.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9486   -0.8777   -1.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9510   -0.3310   -3.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2140    1.7588   -3.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7754    1.4548    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.9125    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222   -0.6084   -2.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -0.7757   -2.2445 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
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 25  1  0
 25 26  1  0
 26 27  2  0
 13 14  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 31  3  1  0
 26 10  1  0
 24 18  1  0
 30  7  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  8 37  1  0
 28 45  1  0
 29 46  1  0
 12 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
M  END


  Mrv1533004241516422D          

 32 35  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
    0.0000   -1.6500    0.0000 O   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   -0.4125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7600    1.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5156    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361    1.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    2.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8210    1.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    2.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    2.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253    2.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0608    3.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759    4.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813    3.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3662    3.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925    0.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -1.1425    0.0000 O   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
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0206693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=CC(=CC=C2C1=O)C1=C(O)C(OC1=O)=C(C(O)=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H14O9/c1-31-16-9-15(25)14-8-11(4-7-13(14)19(16)26)17-20(27)21(32-23(17)30)18(22(28)29)10-2-5-12(24)6-3-10/h2-9,24,27H,1H3,(H,28,29)

> <INCHI_KEY>
KCIVFFGRDAOYNR-UHFFFAOYSA-N

> <FORMULA>
C23H14O9

> <MOLECULAR_WEIGHT>
434.356

> <EXACT_MASS>
434.063782031

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
42.55343254279252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-hydroxy-4-(6-methoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.6599649993333336

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.160980135759974

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4418383592760953

> <JCHEM_PKA_STRONGEST_BASIC>
-4.940320311492387

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
112.94689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.163   1.532   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.019   2.562   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.669   1.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.296   3.259   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.827   3.420   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.454   4.826   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.733   2.174   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.391   4.504   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.859   4.344   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.954   5.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.580   6.996   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.675   8.242   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.112   7.157   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.017   5.911   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.439   0.518   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.409  -0.626   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.729  -2.133   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15    9   16   31                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   30                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   18   31                                                       
CONECT   31   30   15   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-[3-Hydroxy-4-(6-methoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetate	Generator

Chemical Formula

C₂₃H₁₄O₉

Average Mass

434.3560 Da

Monoisotopic Mass

434.06378 Da

IUPAC Name

2-[3-hydroxy-4-(6-methoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

Traditional Name

[3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=CC(=CC=C2C1=O)C1=C(O)C(OC1=O)=C(C(O)=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H14O9/c1-31-16-9-15(25)14-8-11(4-7-13(14)19(16)26)17-20(27)21(32-23(17)30)18(22(28)29)10-2-5-12(24)6-3-10/h2-9,24,27H,1H3,(H,28,29)

InChI Key

KCIVFFGRDAOYNR-UHFFFAOYSA-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
Xerocomus badius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Quinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Enol ester
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Enol
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
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	2.46	ALOGPS
logP	1.66	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	2.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.95 m³·mol⁻¹	ChemAxon
Polarizability	42.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid (NP0206693)

MOL for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D MOL for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D SDF for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D-SDF for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

PDB for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D PDB for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

SMILES for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

INCHI for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

Structure for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)

3D Structure for NP0206693 ([3-hydroxy-4-(6-methoxy-5,8-dioxonaphthalen-2-yl)-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid)