NP-MRD: Showing NP-Card for Asperthecin (NP0004880)

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Record Information

Version

2.0

Created at

2020-12-09 02:17:11 UTC

Updated at

2021-07-15 16:50:25 UTC

NP-MRD ID

NP0004880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperthecin

Provided By

NPAtlas

Description

Asperthecin belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Asperthecin 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. Asperthecin is found in Aspergillus quadrilineatus. Asperthecin was first documented in 1955 (PMID: 14363122). Based on a literature review very few articles have been published on asperthecin (PMID: 31963266) (PMID: 32872591) (PMID: 30539259) (PMID: 26773375).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 33 35  0  0  0  0            999 V2000
   -0.9512   -2.6834    0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4420    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.8765    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    0.4556    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    1.0110   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726    0.2081    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    0.7506    0.1588 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4736    2.1071   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.1305    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.9182    0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.6711    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.0043    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.3125   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.5175   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    0.7492   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    1.5715   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.8986   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.0217   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    1.8600   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -0.3087   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.1765    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -2.4928    0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.6189    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    2.0629   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863    0.4548    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.2260   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.4181    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -2.8924    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -3.6913    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    3.4918   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885    2.8378   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   -0.7589   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -3.2897    0.5691 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  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  1  0  0  0  0
  6  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
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 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  1  0  0  0  0
 21 23  2  0  0  0  0
 23  2  1  0  0  0  0
 11  3  1  0  0  0  0
 23 15  1  0  0  0  0
  5 24  1  0  0  0  0
  7 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
 12 29  1  0  0  0  0
 17 30  1  0  0  0  0
 19 31  1  0  0  0  0
 20 32  1  0  0  0  0
 22 33  1  0  0  0  0
M  END

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.9512   -2.6834    0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4420    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.8765    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    0.4556    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    1.0110   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726    0.2081    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    0.7506    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.1071   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.1305    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.9182    0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.6711    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.0043    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.3125   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.5175   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    0.7492   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    1.5715   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.8986   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.0217   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    1.8600   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -0.3087   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.1765    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -2.4928    0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.6189    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    2.0629   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863    0.4548    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.2260   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.4181    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -2.8924    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -3.6913    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    3.4918   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885    2.8378   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   -0.7589   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -3.2897    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 11  3  1  0
 23 15  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  1  0
M  END


  Mrv1652306242118093D          

 33 35  0  0  0  0            999 V2000
   -0.9512   -2.6834    0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4420    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.8765    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    0.4556    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    1.0110   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726    0.2081    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    0.7506    0.1588 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4736    2.1071   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.1305    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.9182    0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.6711    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.0043    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.3125   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.5175   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    0.7492   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    1.5715   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.8986   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.0217   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    1.8600   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -0.3087   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.1765    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -2.4928    0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.6189    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    2.0629   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863    0.4548    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.2260   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.4181    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -2.8924    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -3.6913    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    3.4918   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885    2.8378   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   -0.7589   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -3.2897    0.5691 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  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  1  0  0  0  0
  6  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
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 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  1  0  0  0  0
 21 23  2  0  0  0  0
 23  2  1  0  0  0  0
 11  3  1  0  0  0  0
 23 15  1  0  0  0  0
  5 24  1  0  0  0  0
  7 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
 12 29  1  0  0  0  0
 17 30  1  0  0  0  0
 19 31  1  0  0  0  0
 20 32  1  0  0  0  0
 22 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(C([H])=C(C(O[H])=C3O[H])C([H])([H])O[H])C(=O)C2=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O8/c16-3-4-1-5-8(15(23)11(4)19)14(22)9-6(17)2-7(18)13(21)10(9)12(5)20/h1-2,16-19,21,23H,3H2

> <INCHI_KEY>
DLOLMYKOOZLTPY-UHFFFAOYSA-N

> <FORMULA>
C15H10O8

> <MOLECULAR_WEIGHT>
318.237

> <EXACT_MASS>
318.037567282

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.452849359644574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,5,6,8-pentahydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
2.583529699

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.975201059737777

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.339429956378727

> <JCHEM_PKA_STRONGEST_BASIC>
-3.077606366139954

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
77.8714

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asperthecin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -0.9512   -2.6834    0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4420    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.8765    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    0.4556    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    1.0110   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726    0.2081    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    0.7506    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.1071   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.1305    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.9182    0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.6711    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.0043    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.3125   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.5175   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    0.7492   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    1.5715   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.8986   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.0217   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    1.8600   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -0.3087   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.1765    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -2.4928    0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.6189    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    2.0629   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863    0.4548    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.2260   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.4181    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -2.8924    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -3.6913    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    3.4918   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885    2.8378   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   -0.7589   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -3.2897    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 11  3  1  0
 23 15  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  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      -0.951  -2.683   0.551  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.853  -1.442   0.324  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.486  -0.877   0.280  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.694   0.456   0.041  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.970   1.011  -0.004  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.073   0.208   0.196  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.463   0.751   0.159  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.474   2.107  -0.094  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.852  -1.131   0.436  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.988  -1.918   0.634  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.597  -1.671   0.479  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.397  -3.004   0.718  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.475   1.313  -0.172  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.252   2.518  -0.386  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.829   0.749  -0.129  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.908   1.571  -0.331  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.845   2.899  -0.576  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.200   1.022  -0.288  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.275   1.860  -0.493  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.397  -0.309  -0.049  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.309  -1.177   0.163  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.548  -2.493   0.397  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.029  -0.619   0.117  0.00  0.00           C+0
HETATM   24  H   UNK     0       2.130   2.063  -0.193  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.986   0.455   1.073  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.961   0.226  -0.709  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.408   2.418   0.005  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.988  -2.892   0.816  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.115  -3.691   0.879  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.109   3.492  -0.653  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.189   2.838  -0.672  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.384  -0.759  -0.010  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.029  -3.290   0.569  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8   25   26                                             
CONECT    8    7   27                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9   28                                                       
CONECT   11    9   12    3                                                  
CONECT   12   11   29                                                       
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   30                                                       
CONECT   18   16   19   20                                                  
CONECT   19   18   31                                                       
CONECT   20   18   21   32                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   33                                                       
CONECT   23   21    2   15                                                  
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   12                                                            
CONECT   30   17                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

RDKit          3D

33 35  0  0  0  0  0  0  0  0999 V2000
   -0.9512   -2.6834    0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4420    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.8765    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    0.4556    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    1.0110   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726    0.2081    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    0.7506    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    2.1071   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522   -1.1305    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -1.9182    0.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.6711    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -3.0043    0.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.3125   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.5175   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    0.7492   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079    1.5715   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.8986   -0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.0217   -0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    1.8600   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -0.3087   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.1765    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -2.4928    0.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -0.6189    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    2.0629   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9863    0.4548    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9610    0.2260   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    2.4181    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -2.8924    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -3.6913    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    3.4918   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885    2.8378   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3838   -0.7589   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0294   -3.2897    0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 11  3  1  0
 23 15  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₈

Average Mass

318.2370 Da

Monoisotopic Mass

318.03757 Da

IUPAC Name

1,2,5,6,8-pentahydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

asperthecin

CAS Registry Number

Not Available

SMILES

OCC1=C(O)C(O)=C2C(=O)C3=C(C(O)=C(O)C=C3O)C(=O)C2=C1

InChI Identifier

InChI=1S/C15H10O8/c16-3-4-1-5-8(15(23)11(4)19)14(22)9-6(17)2-7(18)13(21)10(9)12(5)20/h1-2,16-19,21,23H,3H2

InChI Key

DLOLMYKOOZLTPY-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
Aspergillus quadrilineatus	NPAtlas	14363122

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthraquinone (CHEBI:64161 )

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	1.08	ALOGPS
logP	2.58	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.87 m³·mol⁻¹	ChemAxon
Polarizability	29.45 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

NPAtlas ID

NPA005176

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2341183

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

64161

Good Scents ID

Not Available

References

General References

HOWARD BH, RAISTRICK H: Studies in the biochemistry of micro-organisms. 94. The colouring matters of species in the Aspergillus nidulans group. I. Asperthecin, a crystalline colouring matter of Aspergillus quadrilineatus Thom & Raper. Biochem J. 1955 Mar;59(3):475-84. doi: 10.1042/bj0590475. [PubMed:14363122 ]
Kim MJ, Lee MK, Pham HQ, Gu MJ, Zhu B, Son SH, Hahn D, Shin JH, Yu JH, Park HS, Han KH: The velvet Regulator VosA Governs Survival and Secondary Metabolism of Sexual Spores in Aspergillus nidulans. Genes (Basel). 2020 Jan 16;11(1). pii: genes11010103. doi: 10.3390/genes11010103. [PubMed:31963266 ]
Son YE, Park HS: Genome Wide Analysis Reveals the Role of VadA in Stress Response, Germination, and Sterigmatocystin Production in Aspergillus nidulans Conidia. Microorganisms. 2020 Aug 30;8(9). pii: microorganisms8091319. doi: 10.3390/microorganisms8091319. [PubMed:32872591 ]
Romsdahl J, Blachowicz A, Chiang AJ, Chiang YM, Masonjones S, Yaegashi J, Countryman S, Karouia F, Kalkum M, Stajich JE, Venkateswaran K, Wang CCC: International Space Station conditions alter genomics, proteomics, and metabolomics in Aspergillus nidulans. Appl Microbiol Biotechnol. 2019 Feb;103(3):1363-1377. doi: 10.1007/s00253-018-9525-0. Epub 2018 Dec 12. [PubMed:30539259 ]
Bayram O, Feussner K, Dumkow M, Herrfurth C, Feussner I, Braus GH: Changes of global gene expression and secondary metabolite accumulation during light-dependent Aspergillus nidulans development. Fungal Genet Biol. 2016 Feb;87:30-53. doi: 10.1016/j.fgb.2016.01.004. Epub 2016 Jan 7. [PubMed:26773375 ]

Showing NP-Card for Asperthecin (NP0004880)

MOL for NP0004880 (Asperthecin)

3D MOL for NP0004880 (Asperthecin)

3D SDF for NP0004880 (Asperthecin)

3D-SDF for NP0004880 (Asperthecin)

PDB for NP0004880 (Asperthecin)

3D PDB for NP0004880 (Asperthecin)

SMILES for NP0004880 (Asperthecin)

INCHI for NP0004880 (Asperthecin)

Structure for NP0004880 (Asperthecin)

3D Structure for NP0004880 (Asperthecin)