NP-MRD: Showing NP-Card for Variegatic acid (NP0077824)

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Record Information

Version

2.0

Created at

2022-04-28 22:58:44 UTC

Updated at

2022-04-28 22:58:44 UTC

NP-MRD ID

NP0077824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Variegatic acid

Description

Variegatic acid, also known as variegatate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Variegatic acid is found in Boletus laetissimus Hongo, Caloboletus calopus, Crocinoboletus laetissimus, Suillus bovinus and Suillus variegatus. Variegatic acid was first documented in 2016 (PMID: 27699944). Based on a literature review a small amount of articles have been published on Variegatic acid (PMID: 34081381) (PMID: 31879206) (PMID: 29205129) (PMID: 28032229).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200582D          

 27 29  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -3.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1595   -2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649   -2.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938   -4.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731   -4.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    0.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  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
  6  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
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  0  0  0  0
  1 18  1  0  0  0  0
  4 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    0.7546   -2.6931    0.8462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4305   -1.5379    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293   -0.9672    0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096    0.3537   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7312    1.1584   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.5148   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982    3.2078   -0.9188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503    3.1279   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    0.6000    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580    1.3956    0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    0.9273    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6338   -0.3565    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8963   -0.8174    1.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -1.1394    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1263   -2.4257   -0.3134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4606   -0.6666   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899    0.5898   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848    1.7540   -0.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743   -0.5196    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -0.6370   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.8357   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738   -1.9923   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -0.9343   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -1.1867   -0.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0785    0.2450    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    1.3051    0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6911    0.3774    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    4.1148   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    2.3940    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9366    1.5261    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2841   -1.7065    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4949   -3.0283   -0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729   -1.3063   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    1.6876   -1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600   -2.6666   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080   -2.9377   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6585   -0.4768   -0.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8674    1.2367    0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603    1.3157    0.6132 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 19  1  0
 19 17  2  0
 17 18  1  0
 19 20  1  0
 20 27  2  0
 27 25  1  0
 25 26  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
  5  9  1  0
  9 16  2  0
 16 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
 17  4  1  0
 21 20  1  0
 10  9  1  0
  8 28  1  0
 18 34  1  0
 27 39  1  0
 26 38  1  0
 24 37  1  0
 22 36  1  0
 21 35  1  0
 16 33  1  0
 15 32  1  0
 13 31  1  0
 11 30  1  0
 10 29  1  0
M  END


  Mrv1652304292200582D          

 27 29  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -3.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1595   -2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390   -2.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649   -2.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938   -4.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731   -4.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942    0.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  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
  6  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
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  0  0  0  0
  1 18  1  0  0  0  0
  4 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  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
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077824

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O9/c19-9-3-1-7(5-11(9)21)13-15(23)16(27-18(13)26)14(17(24)25)8-2-4-10(20)12(22)6-8/h1-6,19-23H,(H,24,25)/b16-14+

> <INCHI_KEY>
MRRYHTCWZKZVIH-JQIJEIRASA-N

> <FORMULA>
C18H12O9

> <MOLECULAR_WEIGHT>
372.285

> <EXACT_MASS>
372.048131966

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.899810103799645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.6340271916666664

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.247685132034931

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3471856620073095

> <JCHEM_PKA_STRONGEST_BASIC>
-6.316076856235338

> <JCHEM_POLAR_SURFACE_AREA>
164.74999999999997

> <JCHEM_REFRACTIVITY>
92.04579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.91e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.310  -6.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.936  -5.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.031  -4.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.499  -4.358   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.468  -5.282   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.215  -8.096   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.620  -8.578   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.816  -7.494   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.088  -3.215   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.044  -2.739   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.829  -0.757   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.973  -1.788   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.653  -3.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.438  -1.312   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.149   0.749   0.000  0.00  0.00           O+0
CONECT    1    2    3   18                                                  
CONECT    2    1                                                            
CONECT    3    1    4   20                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    9                                                            
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5    1                                                       
CONECT   19    4                                                            
CONECT   20    3   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   23                                                            
CONECT   27   22                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Variegatate	Generator

Chemical Formula

C₁₈H₁₂O₉

Average Mass

372.2850 Da

Monoisotopic Mass

372.04813 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC(=O)C(=C1\OC(=O)C(=C1O)C1=CC(O)=C(O)C=C1)\C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C18H12O9/c19-9-3-1-7(5-11(9)21)13-15(23)16(27-18(13)26)14(17(24)25)8-2-4-10(20)12(22)6-8/h1-6,19-23H,(H,24,25)/b16-14+

InChI Key

MRRYHTCWZKZVIH-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 laetissimus Hongo	Fungi	KNApSAcK
Caloboletus calopus	LOTUS Database	35616633
Crocinoboletus laetissimus	LOTUS Database	35616633
Suillus bovinus	LOTUS Database	35616633
Suillus variegatus	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	2.16	ALOGPS
logP	1.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.05 m³·mol⁻¹	ChemAxon
Polarizability	34.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00041215

Chemspider ID

74025443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Variegatic acid

METLIN ID

Not Available

PubChem Compound

101967051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Herkersdorf S, Kruger T, Wein P, Loffler S, Fontaine T, Gressler M, Hertweck C, Brakhage AA, Hoffmeister D: Bacterial cell wall-degrading enzymes induce basidiomycete natural product biosynthesis. Environ Microbiol. 2021 Aug;23(8):4360-4371. doi: 10.1111/1462-2920.15621. Epub 2021 Jun 10. [PubMed:34081381 ]
Sugaya K, Ino M, Matsuo N, Onose JI, Abe N: Variegatic acid from the edible mushroom Tylopilus ballouii inhibits TNF-alpha production and PKCbeta1 activity in leukemia cells. Bioorg Med Chem Lett. 2020 Feb 15;30(4):126886. doi: 10.1016/j.bmcl.2019.126886. Epub 2019 Dec 13. [PubMed:31879206 ]
Tauber JP, Gallegos-Monterrosa R, Kovacs AT, Shelest E, Hoffmeister D: Dissimilar pigment regulation in Serpula lacrymans and Paxillus involutus during inter-kingdom interactions. Microbiology (Reading). 2018 Jan;164(1):65-77. doi: 10.1099/mic.0.000582. Epub 2017 Dec 5. [PubMed:29205129 ]
Zhu Y, Mahaney J, Jellison J, Cao J, Gressler J, Hoffmeister D, Goodell B: Fungal variegatic acid and extracellular polysaccharides promote the site-specific generation of reactive oxygen species. J Ind Microbiol Biotechnol. 2017 Mar;44(3):329-338. doi: 10.1007/s10295-016-1889-5. Epub 2016 Dec 29. [PubMed:28032229 ]
Tauber JP, Schroeckh V, Shelest E, Brakhage AA, Hoffmeister D: Bacteria induce pigment formation in the basidiomycete Serpula lacrymans. Environ Microbiol. 2016 Dec;18(12):5218-5227. doi: 10.1111/1462-2920.13558. Epub 2016 Oct 24. [PubMed:27699944 ]

Showing NP-Card for Variegatic acid (NP0077824)

MOL for NP0077824 (Variegatic acid)

3D MOL for NP0077824 (Variegatic acid)

3D SDF for NP0077824 (Variegatic acid)

3D-SDF for NP0077824 (Variegatic acid)

PDB for NP0077824 (Variegatic acid)

3D PDB for NP0077824 (Variegatic acid)

SMILES for NP0077824 (Variegatic acid)

INCHI for NP0077824 (Variegatic acid)

Structure for NP0077824 (Variegatic acid)

3D Structure for NP0077824 (Variegatic acid)