NP-MRD: Showing NP-Card for Lecanoric acid (NP0021392)

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Record Information

Version

2.0

Created at

2021-01-06 06:38:51 UTC

Updated at

2021-08-20 00:00:00 UTC

NP-MRD ID

NP0021392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lecanoric acid

Provided By

NPAtlas

Description

Lecanoric acid, also known as lecanate, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Lecanoric acid is found in Dimelaena oreina, Dolichousnea longissima, Hypotrachyna horrescens, Ochrolechia parella, Parmotrema arnoldii, Parmotrema clavuliferum, Parmotrema stuppeum, Parmotrema tinctorum, Punctelia subrudecta, Pyricularia, Pyricularia FI-178, Stereocaulon curtatum, Umbilicaria torrefacta and Umbilicaria vellea. Lecanoric acid was first documented in 1974 (PMID: 4436144). Based on a literature review very few articles have been published on Lecanoric acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 37 38  0  0  0  0            999 V2000
   -3.9808    0.0415   -2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.1743   -0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.4295   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.5551    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    0.8136    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1585    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -1.3527    0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    0.1595   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.8761   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -2.2885   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.6590   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623    0.6310   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574    0.8383   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.6587   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    1.4357   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925    2.5234   -0.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.4239    1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    0.1628    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0478    2.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.0360    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.2285    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.3383   -0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0736   -0.3868    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1907   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.8498   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3653   -0.9826   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.5271   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -2.5440    0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.5491   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -2.9792   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.5032   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    0.9100    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    2.6698   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    2.6254    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119    0.5201    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.1296    2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6273   -1.2480    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 15 16  1  0  0  0  0
  4 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20  2  1  0  0  0  0
 15  8  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 19 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9808    0.0415   -2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.1743   -0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.4295   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.5551    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    0.8136    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1585    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -1.3527    0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    0.1595   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.8761   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -2.2885   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.6590   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623    0.6310   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574    0.8383   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.6587   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    1.4357   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925    2.5234   -0.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.4239    1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    0.1628    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0478    2.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.0360    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.2285    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.3383   -0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0736   -0.3868    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1907   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.8498   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3653   -0.9826   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.5271   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -2.5440    0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.5491   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -2.9792   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.5032   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    0.9100    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    2.6698   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    2.6254    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119    0.5201    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.1296    2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6273   -1.2480    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
  4 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 23 37  1  0
M  END


  Mrv1652306242105153D          

 37 38  0  0  0  0            999 V2000
   -3.9808    0.0415   -2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.1743   -0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.4295   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.5551    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    0.8136    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1585    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -1.3527    0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    0.1595   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.8761   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -2.2885   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.6590   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623    0.6310   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574    0.8383   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.6587   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    1.4357   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925    2.5234   -0.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.4239    1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    0.1628    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0478    2.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.0360    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.2285    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.3383   -0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0736   -0.3868    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1907   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.8498   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3653   -0.9826   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.5271   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -2.5440    0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.5491   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -2.9792   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.5032   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    0.9100    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    2.6698   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    2.6254    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119    0.5201    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.1296    2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6273   -1.2480    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 15 16  1  0  0  0  0
  4 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20  2  1  0  0  0  0
 15  8  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 16 34  1  0  0  0  0
 17 35  1  0  0  0  0
 19 36  1  0  0  0  0
 23 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C([H])=C(OC(=O)C2=C(C([H])=C(O[H])C([H])=C2O[H])C([H])([H])[H])C([H])=C1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)

> <INCHI_KEY>
HEMSJKZDHNSSEW-UHFFFAOYSA-N

> <FORMULA>
C16H14O7

> <MOLECULAR_WEIGHT>
318.281

> <EXACT_MASS>
318.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.476848825753386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-6-methylbenzoic acid

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
4.708410950333334

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.651348195914757

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8407058631897417

> <JCHEM_PKA_STRONGEST_BASIC>
-4.006403730619771

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
81.14219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lecanoric acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9808    0.0415   -2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.1743   -0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.4295   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.5551    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    0.8136    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1585    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -1.3527    0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    0.1595   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.8761   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -2.2885   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.6590   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623    0.6310   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574    0.8383   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.6587   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    1.4357   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925    2.5234   -0.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.4239    1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    0.1628    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0478    2.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.0360    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.2285    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.3383   -0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0736   -0.3868    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1907   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.8498   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3653   -0.9826   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.5271   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -2.5440    0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.5491   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -2.9792   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.5032   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    0.9100    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    2.6698   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    2.6254    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119    0.5201    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.1296    2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6273   -1.2480    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
  4 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.981   0.042  -2.184  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.213   0.174  -0.936  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.858   0.430  -0.926  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.133   0.555   0.234  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.233   0.814   0.119  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.189  -0.159   0.046  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.766  -1.353   0.088  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.596   0.160  -0.072  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.526  -0.876  -0.143  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.045  -2.289  -0.095  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.883  -0.659  -0.256  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.362   0.631  -0.304  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.757   0.838  -0.420  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.485   1.659  -0.237  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.103   1.436  -0.122  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.293   2.523  -0.061  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.769   0.424   1.427  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.154   0.163   1.433  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.701   0.048   2.691  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.885   0.036   0.280  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.290  -0.229   0.260  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.928  -0.338  -0.842  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.074  -0.387   1.376  0.00  0.00           O+0
HETATM   24  H   UNK     0      -3.234   0.191  -3.032  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.717   0.850  -2.366  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.365  -0.983  -2.374  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.390   0.527  -1.913  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.548  -2.544   0.846  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.402  -2.549  -0.944  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.946  -2.979  -0.164  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.585  -1.503  -0.309  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.279   0.910   0.442  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.827   2.670  -0.271  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.339   2.625   0.017  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.212   0.520   2.349  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.632  -0.130   2.886  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.627  -1.248   1.437  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   28   29   30                                             
CONECT   11    9   12   31                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   32                                                       
CONECT   14   12   15   33                                                  
CONECT   15   14   16    8                                                  
CONECT   16   15   34                                                       
CONECT   17    4   18   35                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   36                                                       
CONECT   20   18   21    2                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   37                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   19                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9808    0.0415   -2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.1743   -0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581    0.4295   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.5551    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331    0.8136    0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894   -0.1585    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -1.3527    0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    0.1595   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -0.8761   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452   -2.2885   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8832   -0.6590   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623    0.6310   -0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574    0.8383   -0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    1.6587   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1035    1.4357   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925    2.5234   -0.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.4239    1.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    0.1628    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    0.0478    2.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853    0.0360    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.2285    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282   -0.3383   -0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0736   -0.3868    1.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1907   -3.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    0.8498   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3653   -0.9826   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.5271   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483   -2.5440    0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018   -2.5491   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461   -2.9792   -0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.5032   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    0.9100    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    2.6698   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389    2.6254    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119    0.5201    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6323   -0.1296    2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6273   -1.2480    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
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 12 14  1  0
 14 15  2  0
 15 16  1  0
  4 17  2  0
 17 18  1  0
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 18 20  2  0
 20 21  1  0
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 20  2  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 23 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,4-Dihydroxy-6-methylbenzoic acid 4-carboxy-3-hydroxy-5-methylphenyl ester	ChEBI
Orsellinate depside	ChEBI
2,4-Dihydroxy-6-methylbenzoate 4-carboxy-3-hydroxy-5-methylphenyl ester	Generator
Orsellinic acid depside	Generator
Lecanate	Generator
Lecanic acid	Generator
Lecanoric acid, monopotassium salt	MeSH
Lecanoric acid	ChEBI
O-Orsellinic acid depside	Generator

Chemical Formula

C₁₆H₁₄O₇

Average Mass

318.2810 Da

Monoisotopic Mass

318.07395 Da

IUPAC Name

4-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-6-methylbenzoic acid

Traditional Name

lecanoric acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OC1=CC(O)=C(C(O)=O)C(C)=C1

InChI Identifier

InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)

InChI Key

HEMSJKZDHNSSEW-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, 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
Dimelaena oreina	LOTUS Database	35616633
Dolichousnea longissima	LOTUS Database	35616633
Hypotrachyna horrescens	LOTUS Database	35616633
Ochrolechia parella	-	KNApSAcK
Parmotrema arnoldii	LOTUS Database	35616633
Parmotrema clavuliferum	LOTUS Database	35616633
Parmotrema stuppeum	LOTUS Database	35616633
Parmotrema tinctorum	LOTUS Database	35616633
Punctelia subrudecta	LOTUS Database	35616633
Pyricularia	NPAtlas	4436144
Pyricularia FI-178	-	KNApSAcK
Stereocaulon curtatum	LOTUS Database	35616633
Umbilicaria torrefacta	LOTUS Database	35616633
Umbilicaria vellea	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Parmelia horrescens	KNApSAcK Database	22123792
Parmelia pseudofatiscens	KNApSAcK Database	22123792
Parmelia tinctorum	KNApSAcK Database	22123792
Thelephora vialis	KNApSAcK Database	22123792
Umbilicaria esculenta	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoate ester
Salicylic acid
Salicylic acid or derivatives
Phenol ester
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
M-cresol
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:15871 )
Depsides and depsidones (C02868 )
Depsides and depsidones (LMPK13080001 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	557.10 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	16.08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.390 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.91	ALOGPS
logP	4.71	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.14 m³·mol⁻¹	ChemAxon
Polarizability	31.48 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA021170

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017999

Chemspider ID

89997

KEGG Compound ID

C02868

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lecanoric acid

METLIN ID

Not Available

PubChem Compound

99613

PDB ID

Not Available

ChEBI ID

15871

Good Scents ID

rw1588321

References

General References

Umezawa H, Shibamoto N, Naganawa H, Ayukawa S, Matsuzaki M, Takeuchi T, Kono K, Sakamoto T: Isolation of lecanoric acid, an inhibitor of histidine decarboxylase from a fungus. J Antibiot (Tokyo). 1974 Aug;27(8):587-96. doi: 10.7164/antibiotics.27.587. [PubMed:4436144 ]

Showing NP-Card for Lecanoric acid (NP0021392)

MOL for NP0021392 (Lecanoric acid)

3D MOL for NP0021392 (Lecanoric acid)

3D SDF for NP0021392 (Lecanoric acid)

3D-SDF for NP0021392 (Lecanoric acid)

PDB for NP0021392 (Lecanoric acid)

3D PDB for NP0021392 (Lecanoric acid)

SMILES for NP0021392 (Lecanoric acid)

INCHI for NP0021392 (Lecanoric acid)

Structure for NP0021392 (Lecanoric acid)

3D Structure for NP0021392 (Lecanoric acid)