NP-MRD: Showing NP-Card for Piloquinone (NP0004831)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:14:41 UTC

Updated at

2021-07-15 16:50:17 UTC

NP-MRD ID

NP0004831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piloquinone

Provided By

NPAtlas

Description

Piloquinone is found in Streptomyces pilosus. Piloquinone was first documented in 1963 (PMID: 14076692). Based on a literature review very few articles have been published on 1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)-9,10-dihydrophenanthrene-9,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 46 48  0  0  0  0            999 V2000
   -0.2657   -2.9557   -2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -2.0084   -1.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.1029   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -1.0648   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -1.9165   -2.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -0.0649   -0.7339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1366   -0.5883    0.5939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9847    0.4318    1.3167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1884    0.8146    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    1.6386    1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -0.2020   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.2066   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -1.1093   -1.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -2.0359   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -2.9093   -2.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -1.1429   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -1.9665   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -0.1856   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.1646    0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    0.7685    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    1.6989    1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6825    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    2.6234    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.6010    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.6802    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.7577    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4195   -3.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -3.5985   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -3.6659   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.0938   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1616    0.9113   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -0.8836    1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.4938    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.0498    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    1.5080   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884    1.2226    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6190   -0.1309    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    2.1756    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    2.3381    2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.3155    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4857    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -3.6071   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    2.3138    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    3.3443    2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.3228    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.7445    1.1915 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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 14  2  1  0  0  0  0
 26 20  1  0  0  0  0
 26 12  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
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 15 42  1  0  0  0  0
 22 43  1  0  0  0  0
 23 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 46  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -0.2657   -2.9557   -2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -2.0084   -1.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.1029   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -1.0648   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -1.9165   -2.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -0.0649   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366   -0.5883    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9847    0.4318    1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884    0.8146    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    1.6386    1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -0.2020   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.2066   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -1.1093   -1.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -2.0359   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -2.9093   -2.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -1.1429   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -1.9665   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -0.1856   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.1646    0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    0.7685    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    1.6989    1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6825    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    2.6234    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.6010    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.6802    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.7577    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4195   -3.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -3.5985   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -3.6659   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.0938   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1616    0.9113   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -0.8836    1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.4938    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.0498    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    1.5080   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884    1.2226    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6190   -0.1309    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    2.1756    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    2.3381    2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.3155    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4857    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -3.6071   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    2.3138    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    3.3443    2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.3228    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.7445    1.1915 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 14  2  1  0
 26 20  1  0
 26 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 15 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
M  END


  Mrv1652306242118093D          

 46 48  0  0  0  0            999 V2000
   -0.2657   -2.9557   -2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -2.0084   -1.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.1029   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -1.0648   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -1.9165   -2.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -0.0649   -0.7339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1366   -0.5883    0.5939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9847    0.4318    1.3167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1884    0.8146    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    1.6386    1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -0.2020   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.2066   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -1.1093   -1.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -2.0359   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -2.9093   -2.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -1.1429   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -1.9665   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -0.1856   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.1646    0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    0.7685    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    1.6989    1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6825    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    2.6234    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.6010    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.6802    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.7577    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4195   -3.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -3.5985   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -3.6659   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.0938   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1616    0.9113   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -0.8836    1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.4938    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.0498    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    1.5080   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884    1.2226    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6190   -0.1309    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    2.1756    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    2.3381    2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.3155    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4857    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -3.6071   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    2.3138    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    3.3443    2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.3228    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.7445    1.1915 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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 14  2  1  0  0  0  0
 26 20  1  0  0  0  0
 26 12  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
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 15 42  1  0  0  0  0
 22 43  1  0  0  0  0
 23 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C(=O)C3=C(O[H])C(=C(C([H])=C3C2=C([H])C([H])=C1[H])C(=O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O5/c1-10(2)7-8-15(22)13-9-14-12-5-4-6-16(23)17(12)20(25)21(26)18(14)19(24)11(13)3/h4-6,9-10,23-24H,7-8H2,1-3H3

> <INCHI_KEY>
UJTRABFYSZAGLW-UHFFFAOYSA-N

> <FORMULA>
C21H20O5

> <MOLECULAR_WEIGHT>
352.386

> <EXACT_MASS>
352.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.8151546776874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)-9,10-dihydrophenanthrene-9,10-dione

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
5.559336612666666

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.34425520035611

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.685031822948334

> <JCHEM_PKA_STRONGEST_BASIC>
-5.673139594395331

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
98.93429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -0.2657   -2.9557   -2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -2.0084   -1.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.1029   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -1.0648   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -1.9165   -2.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -0.0649   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366   -0.5883    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9847    0.4318    1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884    0.8146    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    1.6386    1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -0.2020   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.2066   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -1.1093   -1.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -2.0359   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -2.9093   -2.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -1.1429   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -1.9665   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -0.1856   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.1646    0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    0.7685    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    1.6989    1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6825    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    2.6234    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.6010    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.6802    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.7577    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4195   -3.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -3.5985   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -3.6659   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.0938   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1616    0.9113   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -0.8836    1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.4938    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.0498    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    1.5080   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884    1.2226    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6190   -0.1309    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    2.1756    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    2.3381    2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.3155    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4857    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -3.6071   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    2.3138    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    3.3443    2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.3228    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.7445    1.1915 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 14  2  1  0
 26 20  1  0
 26 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 15 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  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      -0.266  -2.956  -2.875  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.437  -2.008  -1.996  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.344  -1.103  -1.309  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.815  -1.065  -1.419  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.420  -1.917  -2.126  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.634  -0.065  -0.734  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.137  -0.588   0.594  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.985   0.432   1.317  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.188   0.815   0.502  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.173   1.639   1.736  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.305  -0.202  -0.479  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.671  -0.207  -0.342  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.440  -1.109  -1.028  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.826  -2.036  -1.877  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.649  -2.909  -2.531  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.900  -1.143  -0.907  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.595  -1.966  -1.533  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.539  -0.186  -0.030  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.788  -0.165   0.116  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.711   0.769   0.694  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.301   1.699   1.542  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.681   1.683   1.670  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.585   2.623   2.252  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.220   2.601   2.093  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.585   1.680   1.248  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.327   0.758   0.542  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.817  -2.420  -3.694  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.453  -3.599  -3.403  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.932  -3.666  -2.314  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.565   0.094  -1.358  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.162   0.911  -0.678  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.265  -0.884   1.211  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.759  -1.494   0.450  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.348  -0.050   2.249  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.948   1.508  -0.320  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.988   1.223   1.178  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.619  -0.131   0.096  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.747   2.176   0.866  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.876   2.338   2.241  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.429   1.315   2.463  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.345   0.486   0.041  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.337  -3.607  -3.153  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.187   2.314   2.256  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.079   3.344   2.913  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.638   3.323   2.645  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.506   1.744   1.192  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   30   31                                             
CONECT    7    6    8   32   33                                             
CONECT    8    7    9   10   34                                             
CONECT    9    8   35   36   37                                             
CONECT   10    8   38   39   40                                             
CONECT   11    3   12   41                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   42                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   43                                                       
CONECT   23   21   24   44                                                  
CONECT   24   23   25   45                                                  
CONECT   25   24   26   46                                                  
CONECT   26   25   20   12                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   15                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   24                                                            
CONECT   46   25                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

RDKit          3D

46 48  0  0  0  0  0  0  0  0999 V2000
   -0.2657   -2.9557   -2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -2.0084   -1.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.1029   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -1.0648   -1.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199   -1.9165   -2.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -0.0649   -0.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366   -0.5883    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9847    0.4318    1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884    0.8146    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    1.6386    1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047   -0.2020   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -0.2066   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -1.1093   -1.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257   -2.0359   -1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6492   -2.9093   -2.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999   -1.1429   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950   -1.9665   -1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -0.1856   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -0.1646    0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    0.7685    0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012    1.6989    1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6825    1.6699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848    2.6234    2.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    2.6010    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.6802    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.7577    0.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4195   -3.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -3.5985   -3.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9324   -3.6659   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.0938   -1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1616    0.9113   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -0.8836    1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.4938    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.0498    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9480    1.5080   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9884    1.2226    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6190   -0.1309    0.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7465    2.1756    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    2.3381    2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.3155    2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446    0.4857    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -3.6071   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1866    2.3138    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    3.3443    2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.3228    2.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5064    1.7445    1.1915 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 14  2  1  0
 26 20  1  0
 26 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 15 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 25 46  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₅

Average Mass

352.3860 Da

Monoisotopic Mass

352.13107 Da

IUPAC Name

1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)-9,10-dihydrophenanthrene-9,10-dione

Traditional Name

1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC(C)CCC(=O)C1=C(C)C(O)=C2C(=O)C(=O)C3=C(C=CC=C3O)C2=C1

InChI Identifier

InChI=1S/C21H20O5/c1-10(2)7-8-15(22)13-9-14-12-5-4-6-16(23)17(12)20(25)21(26)18(14)19(24)11(13)3/h4-6,9-10,23-24H,7-8H2,1-3H3

InChI Key

UJTRABFYSZAGLW-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
Streptomyces pilosus	NPAtlas	14076692

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenanthraquinones. These are phenanthrene derivatives containing two ketone groups at position C9 and C10, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthraquinones

Direct Parent

Phenanthraquinones

Alternative Parents

Substituents

Phenanthraquinone
Hydrophenanthrene
Butyrophenone
Naphthalene
O-quinone
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	4.07	ALOGPS
logP	5.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.93 m³·mol⁻¹	ChemAxon
Polarizability	37.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001187

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

542652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

624669

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

POLONSKY J, LEDERER E: PILOQUINONE: A NEW PHENANTHRENE-O-QUINONE ISOLATED FROM THE MYCELIUM OF STREPTOMYCES PILOSUS. Nature. 1963 Jul 20;199:285-6. doi: 10.1038/199285a0. [PubMed:14076692 ]

Showing NP-Card for Piloquinone (NP0004831)

MOL for NP0004831 (Piloquinone)

3D MOL for NP0004831 (Piloquinone)

3D SDF for NP0004831 (Piloquinone)

3D-SDF for NP0004831 (Piloquinone)

PDB for NP0004831 (Piloquinone)

3D PDB for NP0004831 (Piloquinone)

SMILES for NP0004831 (Piloquinone)

INCHI for NP0004831 (Piloquinone)

Structure for NP0004831 (Piloquinone)

3D Structure for NP0004831 (Piloquinone)