NP-MRD: Showing NP-Card for Rubrosulphin (NP0082432)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 03:27:52 UTC

Updated at

2022-04-29 03:27:52 UTC

NP-MRD ID

NP0082432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubrosulphin

Description

Rubrosulphin belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Rubrosulphin is found in Aspergillus melleus, Aspergillus sulphureus and Penicillium viridicatum. Rubrosulphin was first documented in 2017 (PMID: 30520600). Based on a literature review very few articles have been published on Rubrosulphin (PMID: 33166747).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205272D          

 39 45  0  0  1  0            999 V2000
    6.8838    0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3645    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6601   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750   -0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9942   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986    0.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2179    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9223    1.9530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0327    1.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3283    0.2834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8091   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1431    0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3261   -1.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    0.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -1.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333   -0.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549    1.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847    1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4496    0.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063   -0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982   -0.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -1.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    0.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0226    0.8619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7577    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -1.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9920   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5882    1.4410    0.0000 O   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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 27 35  1  0  0  0  0
 34 36  1  6  0  0  0
 14 37  1  0  0  0  0
 37 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END

     RDKit          3D

 59 65  0  0  0  0  0  0  0  0999 V2000
    1.1653   -4.2320   -1.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -3.0447   -1.3346 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419   -1.9552   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267   -1.9773   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4540   -0.8778   -0.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.8972   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5898    0.1724   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400    1.2791    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512    1.3571    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750    2.5246    0.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8324    0.2655   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587    0.3030    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6013    1.2193    0.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    0.8412    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015   -0.4391   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.8094   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8423   -1.1120   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -2.2711   -1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1295   -0.4426   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393    0.8311    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3579    1.4451    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5310    0.7880    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031   -0.5022   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028   -1.1459   -0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715   -2.3919   -1.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7589   -1.1833   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7978   -2.3344   -1.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9414   -0.4822   -0.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9362    0.4889    0.6808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2391    1.2477    0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8141    1.5018    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    1.5515    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    2.7121    0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6694    2.4644    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0841    3.4834    1.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0687    2.3701    0.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833    1.0928    0.9025 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1298    1.3095    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0604    0.1248   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291   -4.8619   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -4.0650   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -4.8162   -2.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2697   -2.8420   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3297   -1.8041   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447    2.7735    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3327    2.4620    0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7978   -3.0590   -1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7856   -0.0344    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0951    0.5667    0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4551    1.6673    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2142    2.0922   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7393    2.0655    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0640    2.1348   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6818    0.7653    1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7014    1.8476    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0505    2.0264   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6027    0.3730    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3823   -0.9056    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209    0.3389   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 14 32  1  0
 32 33  2  0
 32 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 19 24  1  0
 24 25  1  0
 24 23  2  0
 23 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 22  1  0
 22 21  2  0
 16  3  1  0
 17 15  1  0
 22 23  1  0
 11  5  1  0
 13 12  1  0
 21 20  1  0
 39  7  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  6 44  1  0
 37 54  1  1
 38 55  1  0
 38 56  1  0
 38 57  1  0
 39 58  1  0
 39 59  1  0
 10 45  1  0
 25 47  1  0
 29 48  1  1
 30 49  1  0
 30 50  1  0
 30 51  1  0
 31 52  1  0
 31 53  1  0
 21 46  1  0
M  END


  Mrv1652304292205272D          

 39 45  0  0  1  0            999 V2000
    6.8838    0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3645    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6601   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750   -0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9942   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986    0.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2179    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9223    1.9530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0327    1.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3283    0.2834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8091   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1431    0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409   -1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3261   -1.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004    0.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3035    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820   -1.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333   -0.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549    1.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1847    1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4496    0.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063   -0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982   -0.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -1.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280   -1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    0.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0226    0.8619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7577    1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068   -1.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9920   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5882    1.4410    0.0000 O   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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 27 35  1  0  0  0  0
 34 36  1  6  0  0  0
 14 37  1  0  0  0  0
 37 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC3=C(C(=O)O[C@H](C)C3)C(O)=C2C2=C1C1=C(O2)C(=O)C2=C(C1=O)C(O)=C1C(=O)O[C@H](C)CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C29H20O10/c1-9-4-11-6-13-8-15(36-3)20-21-25(33)19-14(7-12-5-10(2)38-29(35)18(12)24(19)32)22(30)27(21)39-26(20)16(13)23(31)17(11)28(34)37-9/h6-10,31-32H,4-5H2,1-3H3/t9-,10-/m1/s1

> <INCHI_KEY>
XRRCXEFWLWRGLZ-NXEZZACHSA-N

> <FORMULA>
C29H20O10

> <MOLECULAR_WEIGHT>
528.469

> <EXACT_MASS>
528.105646844

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
54.83533508629256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,23R)-5,19-dihydroxy-29-methoxy-9,23-dimethyl-8,16,22-trioxaheptacyclo[15.12.0.0^{2,15}.0^{4,13}.0^{6,11}.0^{18,27}.0^{20,25}]nonacosa-1(17),2(15),4(13),5,11,18,20(25),26,28-nonaene-3,7,14,21-tetrone

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
5.692386436666666

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.016633442841636

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.269386079601

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1261744071668827

> <JCHEM_POLAR_SURFACE_AREA>
149.57

> <JCHEM_REFRACTIVITY>
136.25219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,23R)-5,19-dihydroxy-29-methoxy-9,23-dimethyl-8,16,22-trioxaheptacyclo[15.12.0.0^{2,15}.0^{4,13}.0^{6,11}.0^{18,27}.0^{20,25}]nonacosa-1(17),2(15),4(13),5,11,18,20(25),26,28-nonaene-3,7,14,21-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      12.850   1.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.880   0.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.432  -1.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.953  -1.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.923  -0.427   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.371   1.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.340   2.208   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.788   3.646   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      16.861   1.967   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      17.413   0.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.444  -0.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.934   0.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.463  -2.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.942  -2.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.390  -0.900   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.359   0.296   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.521   1.588   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.033   1.189   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.953  -0.348   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.580  -1.047   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.500  -2.585   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.289  -0.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.370   1.329   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.742   2.028   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.822   3.566   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.078   2.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.706   1.469   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.625  -0.069   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.917  -0.908   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.836  -2.446   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.253  -0.768   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.172  -2.306   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.039   0.071   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.042   1.609   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.414   2.308   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.249   2.448   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.973  -3.535   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.452  -3.294   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.298   2.690   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   37                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   15   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   29                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   18   25                                                  
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   22   30                                                  
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34   27                                                       
CONECT   36   34                                                            
CONECT   37   14   38                                                       
CONECT   38   37                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
Rubrosulfin	Generator

Chemical Formula

C₂₉H₂₀O₁₀

Average Mass

528.4690 Da

Monoisotopic Mass

528.10565 Da

IUPAC Name

(9R,23R)-5,19-dihydroxy-29-methoxy-9,23-dimethyl-8,16,22-trioxaheptacyclo[15.12.0.0^{2,15}.0^{4,13}.0^{6,11}.0^{18,27}.0^{20,25}]nonacosa-1(17),2(15),4(13),5,11,18,20(25),26,28-nonaene-3,7,14,21-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC3=C(C(=O)O[C@H](C)C3)C(O)=C2C2=C1C1=C(O2)C(=O)C2=C(C1=O)C(O)=C1C(=O)O[C@H](C)CC1=C2

InChI Identifier

InChI=1S/C29H20O10/c1-9-4-11-6-13-8-15(36-3)20-21-25(33)19-14(7-12-5-10(2)38-29(35)18(12)24(19)32)22(30)27(21)39-26(20)16(13)23(31)17(11)28(34)37-9/h6-10,31-32H,4-5H2,1-3H3/t9-,10-/m1/s1

InChI Key

XRRCXEFWLWRGLZ-NXEZZACHSA-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 melleus	Fungi	KNApSAcK
Aspergillus sulphureus	Fungi	KNApSAcK
Penicillium viridicatum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Naphthopyranone
Naphthopyran
Naphthofuran
1-naphthol
2-benzopyran
Naphthalene
Isochromane
Benzopyran
Benzofuran
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous acid
Furan
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.66	ALOGPS
logP	5.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	149.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	136.25 m³·mol⁻¹	ChemAxon
Polarizability	54.84 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049292

Chemspider ID

88298346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85470810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumla D, Sousa E, Marengo A, Dethoup T, Pereira JA, Gales L, Freitas-Silva J, Costa PM, Mistry S, Silva AMS, Kijjoa A: 1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity. Phytochemistry. 2021 Jan;181:112575. doi: 10.1016/j.phytochem.2020.112575. Epub 2020 Nov 6. [PubMed:33166747 ]
Kamiya K, Arai M, Setiawan A, Kobayashi M: Anti-dormant Mycobacterial Activity of Viomellein and Xanthomegnin, Naphthoquinone Dimers Produced by Marine- derived Aspergillus sp. Nat Prod Commun. 2017 Apr;12(4):579-581. [PubMed:30520600 ]

Showing NP-Card for Rubrosulphin (NP0082432)

MOL for NP0082432 (Rubrosulphin)

3D MOL for NP0082432 (Rubrosulphin)

3D SDF for NP0082432 (Rubrosulphin)

3D-SDF for NP0082432 (Rubrosulphin)

PDB for NP0082432 (Rubrosulphin)

3D PDB for NP0082432 (Rubrosulphin)

SMILES for NP0082432 (Rubrosulphin)

INCHI for NP0082432 (Rubrosulphin)

Structure for NP0082432 (Rubrosulphin)

3D Structure for NP0082432 (Rubrosulphin)