NP-MRD: Showing NP-Card for Xerocomic acid (NP0077827)

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Record Information

Version

2.0

Created at

2022-04-28 22:58:52 UTC

Updated at

2022-04-28 22:58:52 UTC

NP-MRD ID

NP0077827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xerocomic acid

Description

Xerocomic acid, also known as xerocomate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Xerocomic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Xerocomic acid has been detected, but not quantified in, mushrooms. This could make xerocomic acid a potential biomarker for the consumption of these foods. Condensation of two units of xerocomic acid form the pigments sclerocitri, badione A, and also norbadione A, which are found in the mushroom Scleroderma citrinum Pers. It is soluble in methanol. . As an example, it is isolated from Serpula lacrymans. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. Variants include isoxeromoic acid and O-methylxerocomic acid. Xerocomic acid is a red-orange pigment found in fungi of the order Boletales (and is named after the genus Xerocomus). Xerocomic acid is found in Boletus erythropus , Boletus laetissimus Hongo, Caloboletus calopus, Crocinoboletus laetissimus, Gomphidius glutinosus , Retiboletus ornatipes, Suillus collinus and Tapinella atrotomentosa. An oxidase acting on xerocomic acid is responsible for the "bluing" reaction seen in mushrooms.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217022D          

 26 28  0  0  0  0            999 V2000
    0.2892    0.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583    2.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208    2.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458   -0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -1.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583   -2.3096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -1.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6909   -2.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  2  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 23  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.2831    2.1804    1.6874 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352    1.2253    1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038    1.0803    0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -0.1096   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9384   -0.5729   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327   -1.7835   -1.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080   -2.5994   -1.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.0622   -1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    0.3069   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0599    1.6618   -0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650    2.4439    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3204    1.8968    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3821    2.7339    0.8702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3423    0.5360    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555   -0.2561    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5072   -0.7162   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045   -1.9189   -0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    0.0643    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -0.1809    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.0593    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9101   -0.1416    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247   -0.6059    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0098   -0.7972    0.7544 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -0.8535   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5675   -1.3120   -1.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -0.6381   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -1.5044   -2.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    2.1593   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1354    3.5230   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242    2.9725    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2400    0.0716    1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2626   -1.3281    0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -2.5757   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9552    0.4246    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4499    0.0522    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5789   -1.1190    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5509   -1.4769   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144   -0.8401   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 18  1  0
 18 16  2  0
 16 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 16  4  1  0
 26 19  1  0
 15  9  1  0
  8 27  1  0
 17 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
 25 37  1  0
 26 38  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
M  END


  Mrv0541 02241217022D          

 26 28  0  0  0  0            999 V2000
    0.2892    0.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583    2.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208    2.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083    1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458   -0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -1.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583   -2.3096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -1.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6909   -2.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  2  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 23  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=C1\OC(=O)C(=C1O)C1=CC=C(O)C(O)=C1)\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O8/c19-10-4-1-8(2-5-10)14(17(23)24)16-15(22)13(18(25)26-16)9-3-6-11(20)12(21)7-9/h1-7,19-22H,(H,23,24)/b16-14+

> <INCHI_KEY>
LJVSOLKVNIGBDE-JQIJEIRASA-N

> <FORMULA>
C18H12O8

> <MOLECULAR_WEIGHT>
356.2831

> <EXACT_MASS>
356.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.17323263425677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-4-(3,4-dihydroxyphenyl)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
1.9375925133333336

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.364481189634464

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.476335053034003

> <JCHEM_PKA_STRONGEST_BASIC>
-6.012710512027682

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
90.06490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2E)-4-(3,4-dihydroxyphenyl)-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.540   1.385   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.308   0.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.386  -1.077   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.000  -0.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.000   0.923   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.232   1.847   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.312   1.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.082   2.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.312   4.157   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.082   5.543   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.772   4.157   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.002   2.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.772   1.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.848   0.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.772  -1.231   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.312  -1.077   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.156  -2.617   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.692  -2.617   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.082  -4.311   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.850  -3.387   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.004  -1.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.772  -0.923   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.232  -1.539   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.078  -3.079   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.464  -4.003   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.156  -5.543   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   23                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8   13                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13    7   12   14                                                  
CONECT   14    2   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    3                                                            
CONECT   19   20                                                            
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23    4   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Xerocomate	Generator
2-[(2E)-4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetate	Generator

Chemical Formula

C₁₈H₁₂O₈

Average Mass

356.2831 Da

Monoisotopic Mass

356.05322 Da

IUPAC Name

2-[(2E)-4-(3,4-dihydroxyphenyl)-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

Traditional Name

[(2E)-4-(3,4-dihydroxyphenyl)-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=CC=C(O)C(O)=C1)\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H12O8/c19-10-4-1-8(2-5-10)14(17(23)24)16-15(22)13(18(25)26-16)9-3-6-11(20)12(21)7-9/h1-7,19-22H,(H,23,24)/b16-14+

InChI Key

LJVSOLKVNIGBDE-JQIJEIRASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Boletus erythropus	Fungi	KNApSAcK
Boletus laetissimus Hongo	Fungi	KNApSAcK
Caloboletus calopus	LOTUS Database	35616633
Crocinoboletus laetissimus	LOTUS Database	35616633
Gomphidius glutinosus	Fungi	KNApSAcK
Retiboletus ornatipes	LOTUS Database	35616633
Suillus collinus	Fungi	KNApSAcK
Tapinella atrotomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Enol ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Enol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.53	ALOGPS
logP	1.94	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.06 m³·mol⁻¹	ChemAxon
Polarizability	34.17 Å³	ChemAxon
Number of Rings	3	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

HMDB0029460

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000581

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Xerocomic acid

METLIN ID

Not Available

PubChem Compound

54730624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Xerocomic acid (NP0077827)

MOL for NP0077827 (Xerocomic acid)

3D MOL for NP0077827 (Xerocomic acid)

3D SDF for NP0077827 (Xerocomic acid)

3D-SDF for NP0077827 (Xerocomic acid)

PDB for NP0077827 (Xerocomic acid)

3D PDB for NP0077827 (Xerocomic acid)

SMILES for NP0077827 (Xerocomic acid)

INCHI for NP0077827 (Xerocomic acid)

Structure for NP0077827 (Xerocomic acid)

3D Structure for NP0077827 (Xerocomic acid)