NP-MRD: Showing NP-Card for Topopyrone C (NP0003534)

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Record Information

Version

2.0

Created at

2020-12-09 00:45:36 UTC

Updated at

2021-07-15 16:46:40 UTC

NP-MRD ID

NP0003534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Topopyrone C

Provided By

NPAtlas

Description

Topopyrone C 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. Topopyrone C is found in Penicillium. Topopyrone C was first documented in 2008 (PMID: 18248813). Based on a literature review a small amount of articles have been published on topopyrone C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 35 38  0  0  0  0            999 V2000
   -4.1250    2.2045    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    0.8261    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -0.2983    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.5296    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -2.5413    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -1.6171    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -2.8118   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -3.9913   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -2.7702   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -1.5762   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.3924    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -0.3981    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    0.7494    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.8764    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    1.9649    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    0.8933    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.0901    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.2723    0.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322    2.1322    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.9398    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.0293   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.2555   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -0.2843    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.5316   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6386   -0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.7533    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193    2.1491    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    2.7164   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3940   -0.2026    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923   -4.3262   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -3.6953   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    4.1565    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    3.0770    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2148   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -1.1852   -0.0790 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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13  2  1  0  0  0  0
 23 16  1  0  0  0  0
 12  6  1  0  0  0  0
 24 10  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 21 34  1  0  0  0  0
 22 35  1  0  0  0  0
M  END

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.1250    2.2045    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    0.8261    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -0.2983    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.5296    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -2.5413    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -1.6171    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -2.8118   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -3.9913   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -2.7702   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -1.5762   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.3924    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -0.3981    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    0.7494    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.8764    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    1.9649    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    0.8933    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.0901    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.2723    0.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322    2.1322    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.9398    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.0293   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.2555   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -0.2843    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.5316   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6386   -0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.7533    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193    2.1491    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    2.7164   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3940   -0.2026    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923   -4.3262   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -3.6953   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    4.1565    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    3.0770    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2148   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -1.1852   -0.0790 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  8 30  1  0
  9 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  1  0
M  END


  Mrv1652306242117483D          

 35 38  0  0  0  0            999 V2000
   -4.1250    2.2045    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    0.8261    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -0.2983    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.5296    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -2.5413    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -1.6171    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -2.8118   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -3.9913   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -2.7702   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -1.5762   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.3924    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -0.3981    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    0.7494    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.8764    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    1.9649    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    0.8933    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.0901    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.2723    0.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322    2.1322    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.9398    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.0293   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.2555   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -0.2843    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.5316   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6386   -0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.7533    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193    2.1491    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    2.7164   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3940   -0.2026    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923   -4.3262   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -3.6953   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    4.1565    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    3.0770    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2148   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -1.1852   -0.0790 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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13  2  1  0  0  0  0
 23 16  1  0  0  0  0
 12  6  1  0  0  0  0
 24 10  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 21 34  1  0  0  0  0
 22 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C4OC(=C([H])C(=O)C4=C(O[H])C([H])=C3C(=O)C2=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H10O7/c1-6-2-10(20)15-12(22)5-9-14(18(15)25-6)17(24)13-8(16(9)23)3-7(19)4-11(13)21/h2-5,19,21-22H,1H3

> <INCHI_KEY>
AWDAPFGGFWZKGB-UHFFFAOYSA-N

> <FORMULA>
C18H10O7

> <MOLECULAR_WEIGHT>
338.271

> <EXACT_MASS>
338.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
32.59641856889701

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,9,11-trihydroxy-2-methyl-7,12-dihydro-4H-1-oxatetraphene-4,7,12-trione

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.206317563

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.947793849787604

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.405000735557938

> <JCHEM_PKA_STRONGEST_BASIC>
-5.384742793288354

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
88.1429

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,9,11-trihydroxy-2-methyl-1-oxatetraphene-4,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.1250    2.2045    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    0.8261    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -0.2983    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.5296    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -2.5413    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -1.6171    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -2.8118   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -3.9913   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -2.7702   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -1.5762   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.3924    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -0.3981    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    0.7494    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.8764    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    1.9649    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    0.8933    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.0901    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.2723    0.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322    2.1322    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.9398    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.0293   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.2555   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -0.2843    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.5316   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6386   -0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.7533    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193    2.1491    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    2.7164   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3940   -0.2026    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923   -4.3262   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -3.6953   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    4.1565    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    3.0770    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2148   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -1.1852   -0.0790 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  8 30  1  0
  9 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  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      -4.125   2.204   0.266  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.548   0.826   0.188  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.310  -0.298   0.149  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.680  -1.530   0.077  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.403  -2.541   0.043  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.314  -1.617   0.044  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.644  -2.812  -0.027  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.302  -3.991  -0.071  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.240  -2.770  -0.055  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.443  -1.576  -0.011  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.245  -0.392   0.060  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.630  -0.398   0.089  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.235   0.749   0.157  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.496   0.876   0.106  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.157   1.965   0.172  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.953   0.893   0.076  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.660   2.090   0.119  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.939   3.272   0.191  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.032   2.132   0.093  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.738   0.940   0.021  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.118   1.029  -0.004  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.052  -0.256  -0.023  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -0.284   0.005  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.917  -1.532  -0.040  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.508  -2.639  -0.106  0.00  0.00           O+0
HETATM   26  H   UNK     0      -3.692   2.753   1.136  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.219   2.149   0.323  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.785   2.716  -0.679  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.394  -0.203   0.177  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.192  -4.326  -0.068  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.306  -3.695  -0.111  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.422   4.157   0.224  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.573   3.077   0.127  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.690   0.215  -0.055  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.601  -1.185  -0.079  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   30                                                       
CONECT    9    7   10   31                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13    6                                                  
CONECT   13   12    2                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   32                                                       
CONECT   19   17   20   33                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   34                                                       
CONECT   22   20   23   35                                                  
CONECT   23   22   24   16                                                  
CONECT   24   23   25   10                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

RDKit          3D

35 38  0  0  0  0  0  0  0  0999 V2000
   -4.1250    2.2045    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    0.8261    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3104   -0.2983    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.5296    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -2.5413    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -1.6171    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -2.8118   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022   -3.9913   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -2.7702   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -1.5762   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -0.3924    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296   -0.3981    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    0.7494    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.8764    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566    1.9649    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    0.8933    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    2.0901    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.2723    0.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322    2.1322    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.9398    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179    1.0293   -0.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0524   -0.2555   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -0.2843    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.5316   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076   -2.6386   -0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.7533    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193    2.1491    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    2.7164   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3940   -0.2026    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1923   -4.3262   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -3.6953   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221    4.1565    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    3.0770    0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899    0.2148   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015   -1.1852   -0.0790 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 24 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  8 30  1  0
  9 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₈H₁₀O₇

Average Mass

338.2710 Da

Monoisotopic Mass

338.04265 Da

IUPAC Name

5,9,11-trihydroxy-2-methyl-7,12-dihydro-4H-1-oxatetraphene-4,7,12-trione

Traditional Name

5,9,11-trihydroxy-2-methyl-1-oxatetraphene-4,7,12-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O)C=C3C(=O)C4=CC(O)=CC(O)=C4C(=O)C3=C2O1

InChI Identifier

InChI=1S/C18H10O7/c1-6-2-10(20)15-12(22)5-9-14(18(15)25-6)17(24)13-8(16(9)23)3-7(19)4-11(13)21/h2-5,19,21-22H,1H3

InChI Key

AWDAPFGGFWZKGB-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
Penicillium	NPAtlas	11099218

Species Where Detected

Species Name	Source	Reference
Phoma sp. BAUA2861	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroxyanthraquinones. These 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
Naphthopyranone
Naphthopyran
Chromone
Benzopyran
1-benzopyran
Aryl ketone
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:66254 )
quinone (CHEBI:66254 )
naphthochromene (CHEBI:66254 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.93	ALOGPS
logP	3.21	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	5.41	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.14 m³·mol⁻¹	ChemAxon
Polarizability	32.6 Å³	ChemAxon
Number of Rings	4	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

NPA011457

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015651

Chemspider ID

8059936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Topopyrone C

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66254

Good Scents ID

Not Available

References

General References

Dallavalle S, Gattinoni S, Mazzini S, Scaglioni L, Merlini L, Tinelli S, Beretta GL, Zunino F: Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors. Bioorg Med Chem Lett. 2008 Feb 15;18(4):1484-9. doi: 10.1016/j.bmcl.2007.12.055. Epub 2007 Dec 25. [PubMed:18248813 ]

Showing NP-Card for Topopyrone C (NP0003534)

MOL for NP0003534 (Topopyrone C)

3D MOL for NP0003534 (Topopyrone C)

3D SDF for NP0003534 (Topopyrone C)

3D-SDF for NP0003534 (Topopyrone C)

PDB for NP0003534 (Topopyrone C)

3D PDB for NP0003534 (Topopyrone C)

SMILES for NP0003534 (Topopyrone C)

INCHI for NP0003534 (Topopyrone C)

Structure for NP0003534 (Topopyrone C)

3D Structure for NP0003534 (Topopyrone C)