NP-MRD: Showing NP-Card for 12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone (NP0272726)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 19:28:03 UTC

Updated at

2022-09-08 19:28:03 UTC

NP-MRD ID

NP0272726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

Description

12-Acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]Tricosa-1(15),2(11),3(8),5,9,16,18(23),20-octaene-4,7,19,22-tetrone belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone is found in Shiraia bambusicola. 12-Acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]Tricosa-1(15),2(11),3(8),5,9,16,18(23),20-octaene-4,7,19,22-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510442D          

 42 46  0  0  0  0            999 V2000
    3.8469   -3.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9279   -2.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -2.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -3.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -3.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -2.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272   -0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383   -0.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524   -1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    0.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    1.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072    1.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914    2.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2453    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592    2.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    2.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    1.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    0.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491   -0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6134   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -0.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5219   -1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -1.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -2.9601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018   -1.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -1.8599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -1.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -1.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  2  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  2  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
   -3.1687   -0.9822    4.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.4589    3.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516   -1.1624    2.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484   -2.3850    1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5436   -3.1863    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -4.3596    0.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634   -2.6351    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -3.3932   -0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1285   -4.6646   -1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339   -2.8699   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -3.6110   -2.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757   -3.5649   -3.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -1.6180   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -0.8828   -0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -1.2966    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.5206    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    0.6132    1.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1720    0.5707   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0184    1.1811   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977    2.5521    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    3.1469    0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1797    4.4445    1.1020 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    2.3997    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    3.0801    1.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5219    3.0972    2.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    1.1310    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    0.3692    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8490    1.1550    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.9917    1.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980    2.0262   -0.3013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155   -0.1050   -1.2326 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3038   -0.5388   -1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7868    1.0312   -2.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -1.1491   -1.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343    3.2836    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136    4.4779    0.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3877    2.6427   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    1.3864   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5045    0.8708   -1.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7850    1.2589   -2.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712    0.5607   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918   -0.5804   -1.3035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236   -2.0143    4.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7359   -0.3504    5.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -0.9811    4.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599   -2.8106    2.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -5.2982   -0.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -4.3193   -3.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699   -3.7122   -4.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -2.5435   -4.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451    5.1730    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422    2.0510    3.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    3.4922    3.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    3.7396    3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852   -0.5554    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797    0.5569    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    1.9874    1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6086    0.3843    1.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9556    0.2701   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155   -1.3560   -2.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022   -1.0116   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    0.7513   -2.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -0.9129   -2.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -2.0783   -1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    3.2480   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104    2.3387   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7425    0.7438   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9814    0.9012   -3.5818 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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 34  1  0
 34 31  1  0
 31 32  1  0
 31 33  1  6
 31 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 27 26  1  0
 26 23  2  0
 23 24  1  0
 24 25  1  0
 23 21  1  0
 21 22  1  0
 21 20  2  0
 20 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 38 41  1  0
 41 42  2  0
 41 19  1  0
 19 18  2  0
 18 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16  3  1  0
 15  7  1  0
 14 13  1  0
 18 26  1  0
 19 20  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 34 63  1  0
 34 64  1  0
 32 59  1  0
 32 60  1  0
 32 61  1  0
 33 62  1  0
 27 55  1  1
 29 56  1  0
 29 57  1  0
 29 58  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 22 51  1  0
 37 65  1  0
 40 66  1  0
 40 67  1  0
 40 68  1  0
M  END


  Mrv1533004241510442D          

 42 46  0  0  0  0            999 V2000
    3.8469   -3.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9279   -2.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -2.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -3.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146   -2.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -3.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -2.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272   -0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383   -0.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524   -1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7787    0.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    1.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072    1.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0914    2.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2453    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592    2.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    2.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    1.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    0.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491   -0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6134   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -0.4943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5219   -1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -1.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -2.9601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018   -1.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -1.8599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -1.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -1.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  2  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  2  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0272726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C(OC)=C3CC(C)(O)C(C(C)=O)C4=C(OC)C(O)=C5C(=O)C=C(OC)C(=O)C5=C4C3=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c1-10(31)23-22-19(21-18(27(37)29(22)42-6)13(33)8-15(40-4)25(21)35)16-11(9-30(23,2)38)28(41-5)26(36)17-12(32)7-14(39-3)24(34)20(16)17/h7-8,23,36-38H,9H2,1-6H3

> <INCHI_KEY>
UVHNWRDTZAYVST-UHFFFAOYSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.90006964467824

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
1.8383028670000001

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.553277139223598

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.873531467863682

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144096726919484

> <JCHEM_POLAR_SURFACE_AREA>
182.95999999999998

> <JCHEM_REFRACTIVITY>
150.5959

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.181  -6.836   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.332  -5.066   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.448  -4.616   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.281  -5.622   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.827  -5.115   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.678  -6.273   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.539  -3.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.085  -3.095   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.144  -4.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.797  -1.582   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.818  -1.213   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.151  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.964  -0.576   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.453   0.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.271   2.182   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.760   2.855   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.037   3.806   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.802   2.356   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.191   3.944   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.711   4.327   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.726   5.531   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.892   1.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.303   1.885   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.761   3.533   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.350   3.808   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.543   0.972   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.053   1.529   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.372  -0.559   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.612  -1.472   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.150  -0.923   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.441  -3.002   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.030  -3.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.598  -5.525   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.225  -6.305   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.790  -2.706   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.326  -3.472   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.961  -1.176   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.721  -0.263   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.418  -1.083   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.706  -2.596   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.160  -3.103   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.480  -2.113   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   40                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   39                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   38                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   37                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   28   38                                                  
CONECT   38   37   22   39                                                  
CONECT   39   38   13   40                                                  
CONECT   40   39    7   41                                                  
CONECT   41   40    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

Traditional Name

12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C(OC)=C3CC(C)(O)C(C(C)=O)C4=C(OC)C(O)=C5C(=O)C=C(OC)C(=O)C5=C4C3=C2C1=O

InChI Identifier

InChI=1S/C30H26O12/c1-10(31)23-22-19(21-18(27(37)29(22)42-6)13(33)8-15(40-4)25(21)35)16-11(9-30(23,2)38)28(41-5)26(36)17-12(32)7-14(39-3)24(34)20(16)17/h7-8,23,36-38H,9H2,1-6H3

InChI Key

UVHNWRDTZAYVST-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Shiraia bambusicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Anisole
Phenol ether
Aryl ketone
Quinone
Alkyl aryl ether
Phenol
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Ketone
Ether
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.04	ALOGPS
logP	1.84	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	182.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.6 m³·mol⁻¹	ChemAxon
Polarizability	55.9 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone (NP0272726)

MOL for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

3D MOL for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

3D SDF for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

3D-SDF for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

PDB for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

3D PDB for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

SMILES for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

INCHI for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

Structure for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)

3D Structure for NP0272726 (12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone)