NP-MRD: Showing NP-Card for Topopyrone A (NP0003532)

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Record Information

Version

1.0

Created at

2020-12-09 00:45:31 UTC

Updated at

2021-07-15 16:46:40 UTC

NP-MRD ID

NP0003532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Topopyrone A

Provided By

NPAtlas

Description

Topopyrone A 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. Topopyrone A 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 A is found in Phoma. It was first documented in 2000 (PMID: 11099218). Based on a literature review a small amount of articles have been published on topopyrone A (PMID: 11099219) (PMID: 19097800) (PMID: 22462811).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 35 38  0  0  0  0            999 V2000
   -4.1065    2.2145    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.8574    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -0.2512    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.5005    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -2.5054    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.5947    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497   -2.8053    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -3.9961    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -2.8101    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140   -1.6789    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.4811    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.4388    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.7127    0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.8038    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.8504    0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.8376    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -0.3814    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -0.3784    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697    0.8170    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793    0.8212    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    2.0071    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    3.5407    0.0935 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6873    2.0626    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    3.2836    0.0712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.6604    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -2.7547    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    2.3783    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    3.0103   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9223    2.2252   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.1287    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317   -4.1936    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -3.7829    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.3210    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    1.7065    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.5343    0.0623 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  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
 25 10  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
 18 33  1  0  0  0  0
 20 34  1  0  0  0  0
 24 35  1  0  0  0  0
M  END

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.1065    2.2145    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.8574    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -0.2512    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.5005    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -2.5054    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.5947    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497   -2.8053    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -3.9961    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -2.8101    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140   -1.6789    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.4811    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.4388    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.7127    0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.8038    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.8504    0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.8376    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -0.3814    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -0.3784    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697    0.8170    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793    0.8212    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    2.0071    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    3.5407    0.0935 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6873    2.0626    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    3.2836    0.0712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.6604    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -2.7547    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    2.3783    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    3.0103   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9223    2.2252   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.1287    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317   -4.1936    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -3.7829    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.3210    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    1.7065    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.5343    0.0623 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
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25 26  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 25 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  8 31  1  0
  9 32  1  0
 18 33  1  0
 20 34  1  0
 24 35  1  0
M  END


  Mrv1652306242117483D          

 35 38  0  0  0  0            999 V2000
   -4.1065    2.2145    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.8574    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -0.2512    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.5005    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -2.5054    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.5947    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497   -2.8053    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -3.9961    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -2.8101    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140   -1.6789    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.4811    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.4388    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.7127    0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.8038    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.8504    0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.8376    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -0.3814    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -0.3784    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697    0.8170    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793    0.8212    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    2.0071    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    3.5407    0.0935 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6873    2.0626    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    3.2836    0.0712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.6604    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -2.7547    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    2.3783    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    3.0103   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9223    2.2252   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.1287    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317   -4.1936    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -3.7829    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.3210    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    1.7065    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.5343    0.0623 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  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
 25 10  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  8 31  1  0  0  0  0
  9 32  1  0  0  0  0
 18 33  1  0  0  0  0
 20 34  1  0  0  0  0
 24 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C3=C4OC(=C([H])C(=O)C4=C(O[H])C([H])=C3C2=O)C([H])([H])[H])C(O[H])=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C18H9ClO7/c1-5-2-8(20)13-9(21)3-7-12(18(13)26-5)16(24)11-6(15(7)23)4-10(22)14(19)17(11)25/h2-4,21-22,25H,1H3

> <INCHI_KEY>
KUCMIJRMIDNZCP-UHFFFAOYSA-N

> <FORMULA>
C18H9ClO7

> <MOLECULAR_WEIGHT>
372.71

> <EXACT_MASS>
372.0036803

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
34.86087569843915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
3.810362239333333

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.807047248066135

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.186766839858351

> <JCHEM_PKA_STRONGEST_BASIC>
-5.384780170923503

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
92.94769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-chloro-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
   -4.1065    2.2145    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.8574    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -0.2512    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.5005    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -2.5054    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.5947    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497   -2.8053    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -3.9961    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -2.8101    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140   -1.6789    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.4811    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.4388    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.7127    0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.8038    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.8504    0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.8376    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -0.3814    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -0.3784    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697    0.8170    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793    0.8212    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    2.0071    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    3.5407    0.0935 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6873    2.0626    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    3.2836    0.0712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.6604    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -2.7547    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    2.3783    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    3.0103   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9223    2.2252   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.1287    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317   -4.1936    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -3.7829    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.3210    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    1.7065    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.5343    0.0623 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
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25 26  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 25 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  8 31  1  0
  9 32  1  0
 18 33  1  0
 20 34  1  0
 24 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      -4.106   2.215   0.026  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.469   0.857   0.037  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.265  -0.251   0.036  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.682  -1.500   0.046  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.410  -2.505   0.045  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.304  -1.595   0.058  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.650  -2.805   0.069  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.296  -3.996   0.070  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.235  -2.810   0.081  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.514  -1.679   0.082  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.162  -0.481   0.071  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.552  -0.439   0.059  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.170   0.713   0.048  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.571   0.804   0.070  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.121   1.850   0.060  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.026   0.838   0.082  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.693  -0.381   0.093  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.080  -0.378   0.105  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.770   0.817   0.105  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.179   0.821   0.117  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.096   2.007   0.094  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       4.934   3.541   0.094  0.00  0.00          Cl+0
HETATM   23  C   UNK     0       2.687   2.063   0.082  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.072   3.284   0.071  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.967  -1.660   0.094  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.584  -2.755   0.104  0.00  0.00           O+0
HETATM   27  H   UNK     0      -4.596   2.378   1.011  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.352   3.010  -0.139  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.922   2.225  -0.724  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.341  -0.129   0.026  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.232  -4.194   0.063  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.263  -3.783   0.090  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.623  -1.321   0.114  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.664   1.706   0.116  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.142   3.534   0.062  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   31                                                       
CONECT    9    7   10   32                                                  
CONECT   10    9   11   25                                                  
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   25                                                  
CONECT   18   17   19   33                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   34                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   16                                                  
CONECT   24   23   35                                                       
CONECT   25   17   26   10                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   18                                                            
CONECT   34   20                                                            
CONECT   35   24                                                            
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
   -4.1065    2.2145    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.8574    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -0.2512    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.5005    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -2.5054    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.5947    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6497   -2.8053    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -3.9961    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2352   -2.8101    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140   -1.6789    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.4811    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.4388    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698    0.7127    0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.8038    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.8504    0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.8376    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929   -0.3814    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -0.3784    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697    0.8170    0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1793    0.8212    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    2.0071    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9338    3.5407    0.0935 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6873    2.0626    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    3.2836    0.0712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.6604    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5845   -2.7547    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5961    2.3783    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3522    3.0103   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9223    2.2252   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.1287    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317   -4.1936    0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -3.7829    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.3210    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6644    1.7065    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    3.5343    0.0623 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
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25 26  2  0
 13  2  1  0
 23 16  1  0
 12  6  1  0
 25 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  8 31  1  0
  9 32  1  0
 18 33  1  0
 20 34  1  0
 24 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₈H₉ClO₇

Average Mass

372.7100 Da

Monoisotopic Mass

372.00368 Da

IUPAC Name

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

Traditional Name

10-chloro-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)=C(Cl)C(O)=C4C(=O)C3=C2O1

InChI Identifier

InChI=1S/C18H9ClO7/c1-5-2-8(20)13-9(21)3-7-12(18(13)26-5)16(24)11-6(15(7)23)4-10(22)14(19)17(11)25/h2-4,21-22,25H,1H3

InChI Key

KUCMIJRMIDNZCP-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
Phoma	NPAtlas	11099218

Species Where Detected

Species Name	Source	Reference
Phoma sp. BAUA2861	KNApSAcK Database	22123792

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
Naphthopyranone
Naphthopyran
Chromone
Benzopyran
1-benzopyran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Aryl chloride
Aryl halide
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Organohalogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organochloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:66252 )
phenols (CHEBI:66252 )
quinone (CHEBI:66252 )
naphthochromene (CHEBI:66252 )

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	3.38	ALOGPS
logP	3.81	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.19	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	92.95 m³·mol⁻¹	ChemAxon
Polarizability	34.86 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

NPA019045

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015649

Chemspider ID

7996597

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

66252

Good Scents ID

Not Available

References

General References

Kanai Y, Ishiyama D, Senda H, Iwatani W, Takahashi H, Konno H, Tokumasu S, Kanazawa S: Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. I. Producing strain, fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo). 2000 Sep;53(9):863-72. doi: 10.7164/antibiotics.53.863. [PubMed:11099218 ]
Ishiyama D, Kanai Y, Senda H, Iwatani W, Iwatani W, Konno H, Kanazawa S: Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. II. Structure elucidation. J Antibiot (Tokyo). 2000 Sep;53(9):873-8. doi: 10.7164/antibiotics.53.873. [PubMed:11099219 ]
Scaglioni L, Mazzini S, Mondelli R, Dallavalle S, Gattinoni S, Tinelli S, Beretta GL, Zunino F, Ragg E: Interaction between double helix DNA fragments and a new topopyrone acting as human topoisomerase I poison. Bioorg Med Chem. 2009 Jan 15;17(2):484-91. doi: 10.1016/j.bmc.2008.12.005. Epub 2008 Dec 10. [PubMed:19097800 ]
Zaleski PA, Maini R, Leiris SJ, Elban MA, Hecht SM: Synthesis and biological activities of topopyrones. J Nat Prod. 2012 Apr 27;75(4):577-85. doi: 10.1021/np200777z. Epub 2012 Mar 30. [PubMed:22462811 ]

Showing NP-Card for Topopyrone A (NP0003532)

MOL for NP0003532 (Topopyrone A)

3D MOL for NP0003532 (Topopyrone A)

3D SDF for NP0003532 (Topopyrone A)

3D-SDF for NP0003532 (Topopyrone A)

PDB for NP0003532 (Topopyrone A)

3D PDB for NP0003532 (Topopyrone A)

SMILES for NP0003532 (Topopyrone A)

INCHI for NP0003532 (Topopyrone A)

Structure for NP0003532 (Topopyrone A)

3D Structure for NP0003532 (Topopyrone A)