NP-MRD: Showing NP-Card for Atromentin (NP0021762)

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Record Information

Version

2.0

Created at

2021-01-06 07:01:58 UTC

Updated at

2021-07-15 17:37:13 UTC

NP-MRD ID

NP0021762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Atromentin

Provided By

NPAtlas

Description

Atromentin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Atromentin is found in Hydnellum diabolus, Omphalotus subilludens and Tapinella atrotomentosa. Atromentin was first documented in 1965 (PMID: 5862512). Based on a literature review a small amount of articles have been published on Atromentin (PMID: 12872944) (PMID: 12895540) (PMID: 17323650) (PMID: 18805498).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 36 38  0  0  0  0            999 V2000
   -1.5289   -1.2427   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -0.6696   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.7230   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -1.3936   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.1357   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.1624   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.0471   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.0644   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887   -0.2041   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0737   -0.2217   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850   -0.3227    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -0.3002    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    0.5607    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268    1.1198    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    0.6068    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    1.2778    2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.0207    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    0.0471    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.2025    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.1554    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583    0.1404    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    0.1889    0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936    0.3893   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.3382   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.6252   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    0.0661   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.0306   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6718    0.5778   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -0.4318    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -0.3972    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.3070    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4395    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208   -0.3513    2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5109    1.0478    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7110    0.6218   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    0.5363   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17  2  1  0  0  0  0
 24 18  1  0  0  0  0
 12  6  1  0  0  0  0
  4 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 30  1  0  0  0  0
 16 31  1  0  0  0  0
 19 32  1  0  0  0  0
 20 33  1  0  0  0  0
 22 34  1  0  0  0  0
 23 35  1  0  0  0  0
 24 36  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.5289   -1.2427   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -0.6696   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.7230   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -1.3936   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.1357   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.1624   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.0471   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.0644   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887   -0.2041   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0737   -0.2217   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850   -0.3227    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -0.3002    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    0.5607    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268    1.1198    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    0.6068    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    1.2778    2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.0207    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    0.0471    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.2025    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.1554    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583    0.1404    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    0.1889    0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936    0.3893   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.3382   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.6252   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    0.0661   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.0306   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6718    0.5778   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -0.4318    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -0.3972    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.3070    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4395    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208   -0.3513    2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5109    1.0478    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7110    0.6218   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    0.5363   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 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
 17  2  1  0
 24 18  1  0
 12  6  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  1  0
M  END


  Mrv1652306242105183D          

 36 38  0  0  0  0            999 V2000
   -1.5289   -1.2427   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -0.6696   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.7230   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -1.3936   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.1357   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.1624   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.0471   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.0644   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887   -0.2041   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0737   -0.2217   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850   -0.3227    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -0.3002    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    0.5607    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268    1.1198    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    0.6068    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    1.2778    2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.0207    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    0.0471    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.2025    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.1554    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583    0.1404    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    0.1889    0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936    0.3893   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.3382   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.6252   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    0.0661   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.0306   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6718    0.5778   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -0.4318    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -0.3972    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.3070    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4395    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208   -0.3513    2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5109    1.0478    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7110    0.6218   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    0.5363   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17  2  1  0  0  0  0
 24 18  1  0  0  0  0
 12  6  1  0  0  0  0
  4 25  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 30  1  0  0  0  0
 16 31  1  0  0  0  0
 19 32  1  0  0  0  0
 20 33  1  0  0  0  0
 22 34  1  0  0  0  0
 23 35  1  0  0  0  0
 24 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C(O[H])C(=O)C(=C(O[H])C1=O)C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H

> <INCHI_KEY>
FKQQKMGWCJGUCS-UHFFFAOYSA-N

> <FORMULA>
C18H12O6

> <MOLECULAR_WEIGHT>
324.288

> <EXACT_MASS>
324.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5782115197632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.715843396

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.351577488861988

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.038257789819522

> <JCHEM_PKA_STRONGEST_BASIC>
-5.392704566334623

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
87.82960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
atromentin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.5289   -1.2427   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -0.6696   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.7230   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -1.3936   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.1357   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.1624   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.0471   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.0644   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887   -0.2041   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0737   -0.2217   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850   -0.3227    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -0.3002    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    0.5607    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268    1.1198    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    0.6068    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    1.2778    2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.0207    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    0.0471    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.2025    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.1554    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583    0.1404    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    0.1889    0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936    0.3893   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.3382   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.6252   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    0.0661   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.0306   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6718    0.5778   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -0.4318    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -0.3972    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.3070    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4395    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208   -0.3513    2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5109    1.0478    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7110    0.6218   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    0.5363   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 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
 17  2  1  0
 24 18  1  0
 12  6  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  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  O   UNK     0      -1.529  -1.243  -1.822  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.813  -0.670  -0.948  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.656  -0.723  -1.085  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.210  -1.394  -2.150  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.442  -0.136  -0.196  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.911  -0.162  -0.289  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.540  -0.047  -1.505  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.931  -0.064  -1.634  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.689  -0.204  -0.487  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.074  -0.222  -0.618  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.085  -0.323   0.748  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.704  -0.300   0.826  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.794   0.561   0.915  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.527   1.120   1.758  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.634   0.607   1.039  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.207   1.278   2.103  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.459   0.021   0.155  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.890   0.047   0.313  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.476  -0.203   1.541  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.865  -0.155   1.685  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.658   0.140   0.601  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.048   0.189   0.742  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.094   0.389  -0.618  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.716   0.338  -0.740  0.00  0.00           C+0
HETATM   25  H   UNK     0       0.753  -1.625  -3.011  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.974   0.066  -2.416  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.375   0.031  -2.623  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.672   0.578  -0.588  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.706  -0.432   1.633  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.268  -0.397   1.794  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.224   2.307   2.042  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.858  -0.440   2.387  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.321  -0.351   2.644  0.00  0.00           H+0
HETATM   34  H   UNK     0      -7.511   1.048   0.993  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.711   0.622  -1.477  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.299   0.536  -1.709  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   25                                                       
CONECT    5    3    6   13                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   28                                                       
CONECT   11    9   12   29                                                  
CONECT   12   11    6   30                                                  
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   31                                                       
CONECT   17   15   18    2                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   32                                                  
CONECT   20   19   21   33                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   34                                                       
CONECT   23   21   24   35                                                  
CONECT   24   23   18   36                                                  
CONECT   25    4                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   16                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -1.5289   -1.2427   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -0.6696   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.7230   -1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -1.3936   -2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.1357   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -0.1624   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -0.0471   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9308   -0.0644   -1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887   -0.2041   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0737   -0.2217   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850   -0.3227    0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7040   -0.3002    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944    0.5607    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5268    1.1198    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    0.6068    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    1.2778    2.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589    0.0207    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896    0.0471    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.2025    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.1554    1.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583    0.1404    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0475    0.1889    0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936    0.3893   -0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.3382   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.6252   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    0.0661   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    0.0306   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6718    0.5778   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057   -0.4318    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685   -0.3972    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    2.3070    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4395    2.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208   -0.3513    2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5109    1.0478    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7110    0.6218   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2992    0.5363   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 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
 17  2  1  0
 24 18  1  0
 12  6  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 23 35  1  0
 24 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1(4),2(3),2(6),3(4)-Tetrahydroxy[1(1),2(1):2(4),3(1)-terphenyl]-2(2),2(5)-dione	ChEBI
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone	ChEBI
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione	ChEBI
2,5-Dihydroxy-3,6-bis(p-hydroxyphenyl)-p-benzoquinone	ChEBI

Chemical Formula

C₁₈H₁₂O₆

Average Mass

324.2880 Da

Monoisotopic Mass

324.06339 Da

IUPAC Name

2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione

Traditional Name

atromentin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H

InChI Key

FKQQKMGWCJGUCS-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
Hydnellum diabolus	NPAtlas	5862512
Omphalotus subilludens	LOTUS Database	35616633
Tapinella atrotomentosa	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Thelephora aurantiotincta	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Enol
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.98	ALOGPS
logP	2.72	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	5.04	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.83 m³·mol⁻¹	ChemAxon
Polarizability	32.58 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

NPAtlas ID

NPA018419

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036784

Chemspider ID

89570

KEGG Compound ID

Not Available

BioCyc ID

CPD-14619

BiGG ID

Not Available

Wikipedia Link

Atromentin

METLIN ID

Not Available

PubChem Compound

99148

PDB ID

Not Available

ChEBI ID

149660

Good Scents ID

Not Available

References

General References

Khanna JM, Malone MH, Euler KL, Brady LR: Atromentin, anticoagulant from Hydnellum diabolus. J Pharm Sci. 1965 Jul;54(7):1016-20. doi: 10.1002/jps.2600540714. [PubMed:5862512 ]
Hu L, Liu JK: p-Terphenyls from the basidiomycete Thelephora aurantiotincta. Z Naturforsch C J Biosci. 2003 May-Jun;58(5-6):452-4. doi: 10.1515/znc-2003-5-627. [PubMed:12872944 ]
Ngoc Quang D, Hashimoto T, Hitaka Y, Tanaka M, Nukada M, Yamamoto I, Asakawa Y: Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry. 2003 Aug;63(8):919-24. doi: 10.1016/s0031-9422(03)00220-6. [PubMed:12895540 ]
Zheng CJ, Sohn MJ, Kim WG: Atromentin and leucomelone, the first inhibitors specific to enoyl-ACP reductase (FabK) of Streptococcus pneumoniae. J Antibiot (Tokyo). 2006 Dec;59(12):808-12. doi: 10.1038/ja.2006.108. [PubMed:17323650 ]
Schneider P, Bouhired S, Hoffmeister D: Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides. Fungal Genet Biol. 2008 Nov;45(11):1487-96. doi: 10.1016/j.fgb.2008.08.009. Epub 2008 Sep 6. [PubMed:18805498 ]

Showing NP-Card for Atromentin (NP0021762)

MOL for NP0021762 (Atromentin)

3D MOL for NP0021762 (Atromentin)

3D SDF for NP0021762 (Atromentin)

3D-SDF for NP0021762 (Atromentin)

PDB for NP0021762 (Atromentin)

3D PDB for NP0021762 (Atromentin)

SMILES for NP0021762 (Atromentin)

INCHI for NP0021762 (Atromentin)

Structure for NP0021762 (Atromentin)

3D Structure for NP0021762 (Atromentin)