NP-MRD: Showing NP-Card for Asperflavin ribofuranoside (NP0006412)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 03:26:07 UTC

Updated at

2021-07-15 16:54:43 UTC

NP-MRD ID

NP0006412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperflavin ribofuranoside

Provided By

NPAtlas

Description

(3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydroanthracen-1-one belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Asperflavin ribofuranoside is found in Microsporum sp. Asperflavin ribofuranoside was first documented in 2006 (PMID: 16755063). Based on a literature review very few articles have been published on (3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydroanthracen-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 54 57  0  0  0  0            999 V2000
   -0.5236    4.8476   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    3.6919   -0.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    2.4852   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    2.3869   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    1.1950   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392    1.2150    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    0.0981    0.3145 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4888   -0.1153   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6282   -0.5950   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1410   -1.8614   -0.7378 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4107   -1.5625   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8138    1.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4813   -0.6002    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.2544    1.6237 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8815    1.5154    1.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    0.0727    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.1214   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790   -1.0209   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.9839   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223    0.2535   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    1.4230   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918    2.6280   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3126   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778    0.2170   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315    1.0547   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8109   -0.7858    0.0934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1073   -2.0401    0.4532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1269   -2.2760    1.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -3.1114   -0.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -2.2055   -0.0595 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1344    4.7275   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    5.0439   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    5.7462   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    3.2868   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -0.8585    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.2117   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -2.6848   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -2.1576   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.3168   -2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -1.7980    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3028   -1.0252    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.0411    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    1.9866    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -0.8748    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.9510    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    2.7930   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660   -0.2952    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.9486   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205   -3.3461    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2202    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -1.5656    2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9804   -2.9308   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -2.8804    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -2.7842   -1.0198 H   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  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  6  0  0  0
 27 30  1  0  0  0  0
 23  3  1  0  0  0  0
 14  7  1  0  0  0  0
 23 17  1  0  0  0  0
 30 19  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  4 34  1  0  0  0  0
  7 35  1  1  0  0  0
  9 36  1  1  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  6  0  0  0
 13 41  1  0  0  0  0
 14 42  1  1  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 18 45  1  0  0  0  0
 22 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
 29 52  1  0  0  0  0
 30 53  1  0  0  0  0
 30 54  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.5236    4.8476   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    3.6919   -0.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    2.4852   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    2.3869   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    1.1950   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392    1.2150    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    0.0981    0.3145 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4888   -0.1153   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6282   -0.5950   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1410   -1.8614   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4107   -1.5625   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8138    1.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4813   -0.6002    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.2544    1.6237 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8815    1.5154    1.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    0.0727    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.1214   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790   -1.0209   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.9839   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223    0.2535   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    1.4230   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918    2.6280   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3126   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778    0.2170   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315    1.0547   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8109   -0.7858    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1073   -2.0401    0.4532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1269   -2.2760    1.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -3.1114   -0.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -2.2055   -0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    4.7275   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    5.0439   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    5.7462   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    3.2868   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -0.8585    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.2117   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -2.6848   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -2.1576   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.3168   -2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -1.7980    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3028   -1.0252    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.0411    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    1.9866    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -0.8748    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.9510    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    2.7930   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660   -0.2952    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.9486   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205   -3.3461    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2202    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -1.5656    2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9804   -2.9308   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -2.8804    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -2.7842   -1.0198 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  6
 27 30  1  0
 23  3  1  0
 14  7  1  0
 23 17  1  0
 30 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  1
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 14 42  1  1
 15 43  1  0
 16 44  1  0
 18 45  1  0
 22 46  1  0
 26 47  1  0
 26 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 30 53  1  0
 30 54  1  0
M  END


  Mrv1652306242118273D          

 54 57  0  0  0  0            999 V2000
   -0.5236    4.8476   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    3.6919   -0.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    2.4852   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    2.3869   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    1.1950   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392    1.2150    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    0.0981    0.3145 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4888   -0.1153   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6282   -0.5950   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1410   -1.8614   -0.7378 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4107   -1.5625   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8138    1.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4813   -0.6002    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.2544    1.6237 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8815    1.5154    1.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    0.0727    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.1214   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790   -1.0209   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.9839   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223    0.2535   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    1.4230   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918    2.6280   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3126   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778    0.2170   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315    1.0547   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8109   -0.7858    0.0934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1073   -2.0401    0.4532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1269   -2.2760    1.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -3.1114   -0.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -2.2055   -0.0595 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1344    4.7275   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    5.0439   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    5.7462   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    3.2868   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -0.8585    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.2117   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -2.6848   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -2.1576   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.3168   -2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -1.7980    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3028   -1.0252    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.0411    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    1.9866    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -0.8748    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.9510    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    2.7930   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660   -0.2952    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.9486   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205   -3.3461    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2202    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -1.5656    2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9804   -2.9308   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -2.8804    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -2.7842   -1.0198 H   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  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  6  0  0  0
 27 30  1  0  0  0  0
 23  3  1  0  0  0  0
 14  7  1  0  0  0  0
 23 17  1  0  0  0  0
 30 19  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  4 34  1  0  0  0  0
  7 35  1  1  0  0  0
  9 36  1  1  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  6  0  0  0
 13 41  1  0  0  0  0
 14 42  1  1  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 18 45  1  0  0  0  0
 22 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
 29 52  1  0  0  0  0
 30 53  1  0  0  0  0
 30 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(OC([H])([H])[H])=C([H])C(O[C@@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@@]3([H])O[H])=C([H])C2=C([H])C2=C1C(=O)C([H])([H])[C@](O[H])(C([H])([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O9/c1-21(27)6-10-3-9-4-11(29-20-19(26)17(24)14(8-22)30-20)5-13(28-2)16(9)18(25)15(10)12(23)7-21/h3-5,14,17,19-20,22,24-27H,6-8H2,1-2H3/t14-,17-,19-,20+,21+/m1/s1

> <INCHI_KEY>
GPKKBAJJMITEJA-LZHVCYTJSA-N

> <FORMULA>
C21H24O9

> <MOLECULAR_WEIGHT>
420.414

> <EXACT_MASS>
420.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.49301965106745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydroanthracen-1-one

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.5678319659999995

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.262827485043607

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.996710187656876

> <JCHEM_PKA_STRONGEST_BASIC>
-2.931928977887341

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
103.53749999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-2,4-dihydroanthracen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.5236    4.8476   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    3.6919   -0.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    2.4852   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    2.3869   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    1.1950   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392    1.2150    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    0.0981    0.3145 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4888   -0.1153   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6282   -0.5950   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1410   -1.8614   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4107   -1.5625   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8138    1.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4813   -0.6002    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.2544    1.6237 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8815    1.5154    1.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    0.0727    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.1214   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790   -1.0209   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.9839   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223    0.2535   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    1.4230   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918    2.6280   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3126   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778    0.2170   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315    1.0547   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8109   -0.7858    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1073   -2.0401    0.4532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1269   -2.2760    1.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -3.1114   -0.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -2.2055   -0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    4.7275   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    5.0439   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    5.7462   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    3.2868   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -0.8585    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.2117   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -2.6848   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -2.1576   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.3168   -2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -1.7980    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3028   -1.0252    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.0411    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    1.9866    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -0.8748    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.9510    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    2.7930   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660   -0.2952    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.9486   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205   -3.3461    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2202    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -1.5656    2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9804   -2.9308   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -2.8804    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -2.7842   -1.0198 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  6
 27 30  1  0
 23  3  1  0
 14  7  1  0
 23 17  1  0
 30 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  1
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 14 42  1  1
 15 43  1  0
 16 44  1  0
 18 45  1  0
 22 46  1  0
 26 47  1  0
 26 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 30 53  1  0
 30 54  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      -0.524   4.848  -0.861  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.311   3.692  -0.758  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.676   2.485  -0.499  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.679   2.387  -0.344  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.366   1.195  -0.083  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.739   1.215   0.056  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.518   0.098   0.315  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.489  -0.115  -0.663  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.628  -0.595  -0.083  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.141  -1.861  -0.738  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.411  -1.563  -2.076  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.373  -0.814   1.394  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.481  -0.600   2.175  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.294   0.254   1.624  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.882   1.515   1.628  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.580   0.073   0.016  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.802   0.121  -0.135  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.579  -1.021  -0.032  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.942  -0.984  -0.179  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.522   0.254  -0.437  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.805   1.423  -0.549  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.392   2.628  -0.800  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.419   1.313  -0.389  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.978   0.217  -0.595  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.532   1.055  -1.332  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.811  -0.786   0.093  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.107  -2.040   0.453  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.127  -2.276   1.970  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.863  -3.111  -0.083  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.716  -2.205  -0.060  0.00  0.00           C+0
HETATM   31  H   UNK     0       0.134   4.728  -1.762  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.122   5.044  -0.005  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.176   5.746  -1.017  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.299   3.287  -0.424  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.977  -0.859   0.412  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.400   0.212  -0.140  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.417  -2.685  -0.617  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.105  -2.158  -0.286  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.230  -2.317  -2.678  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.897  -1.798   1.535  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.303  -1.025   3.064  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.684   0.041   2.500  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.764   1.987   0.749  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.043  -0.875   0.215  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.047  -1.951   0.172  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.347   2.793  -0.906  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.166  -0.295   1.047  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.738  -0.949  -0.498  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.821  -3.346   2.147  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.186  -2.220   2.296  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.502  -1.566   2.509  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.980  -2.931  -1.067  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.178  -2.880   0.669  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.711  -2.784  -1.020  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   34                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14   35                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   12   36                                             
CONECT   10    9   11   37   38                                             
CONECT   11   10   39                                                       
CONECT   12    9   13   14   40                                             
CONECT   13   12   41                                                       
CONECT   14   12   15    7   42                                             
CONECT   15   14   43                                                       
CONECT   16    5   17   44                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   45                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   46                                                       
CONECT   23   21    3   17                                                  
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   47   48                                             
CONECT   27   26   28   29   30                                             
CONECT   28   27   49   50   51                                             
CONECT   29   27   52                                                       
CONECT   30   27   19   53   54                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   18                                                            
CONECT   46   22                                                            
CONECT   47   26                                                            
CONECT   48   26                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
CONECT   51   28                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   30                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -0.5236    4.8476   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    3.6919   -0.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    2.4852   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6788    2.3869   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    1.1950   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392    1.2150    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    0.0981    0.3145 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4888   -0.1153   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6282   -0.5950   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1410   -1.8614   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4107   -1.5625   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8138    1.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4813   -0.6002    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.2544    1.6237 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8815    1.5154    1.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    0.0727    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.1214   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5790   -1.0209   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.9839   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223    0.2535   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    1.4230   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918    2.6280   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3126   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778    0.2170   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315    1.0547   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8109   -0.7858    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1073   -2.0401    0.4532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1269   -2.2760    1.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633   -3.1114   -0.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7157   -2.2055   -0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    4.7275   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    5.0439   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    5.7462   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2987    3.2868   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -0.8585    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3997    0.2117   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -2.6848   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1051   -2.1576   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303   -2.3168   -2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -1.7980    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3028   -1.0252    3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    0.0411    2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    1.9866    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -0.8748    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.9510    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    2.7930   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1660   -0.2952    1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7376   -0.9486   -0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205   -3.3461    2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861   -2.2202    2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -1.5656    2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9804   -2.9308   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -2.8804    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -2.7842   -1.0198 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  5 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  6
 27 30  1  0
 23  3  1  0
 14  7  1  0
 23 17  1  0
 30 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  1
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 14 42  1  1
 15 43  1  0
 16 44  1  0
 18 45  1  0
 22 46  1  0
 26 47  1  0
 26 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 30 53  1  0
 30 54  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₉

Average Mass

420.4140 Da

Monoisotopic Mass

420.14203 Da

IUPAC Name

(3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydroanthracen-1-one

Traditional Name

(3S)-6-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,9-dihydroxy-8-methoxy-3-methyl-2,4-dihydroanthracen-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=CC2=CC3=C(C(=O)C[C@@](C)(O)C3)C(O)=C12

InChI Identifier

InChI=1S/C21H24O9/c1-21(27)6-10-3-9-4-11(29-20-19(26)17(24)14(8-22)30-20)5-13(28-2)16(9)18(25)15(10)12(23)7-21/h3-5,14,17,19-20,22,24-27H,6-8H2,1-2H3/t14-,17-,19-,20+,21+/m1/s1

InChI Key

GPKKBAJJMITEJA-LZHVCYTJSA-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
Microsporum sp.	NPAtlas	16755063

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Anthracene
1-naphthol
O-glycosyl compound
Pentose monosaccharide
Tetralin
Anisole
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monosaccharide
Tertiary alcohol
Oxolane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Aldehyde
Organic oxide
Primary alcohol
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	0.73	ALOGPS
logP	0.57	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.54 m³·mol⁻¹	ChemAxon
Polarizability	43.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002633

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9728319

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11553541

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li Y, Li X, Lee U, Kang JS, Choi HD, Sona BW: A new radical scavenging anthracene glycoside, asperflavin ribofuranoside, and polyketides from a marine isolate of the fungus microsporum. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):882-3. doi: 10.1248/cpb.54.882. [PubMed:16755063 ]

Showing NP-Card for Asperflavin ribofuranoside (NP0006412)

MOL for NP0006412 (Asperflavin ribofuranoside)

3D MOL for NP0006412 (Asperflavin ribofuranoside)

3D SDF for NP0006412 (Asperflavin ribofuranoside)

3D-SDF for NP0006412 (Asperflavin ribofuranoside)

PDB for NP0006412 (Asperflavin ribofuranoside)

3D PDB for NP0006412 (Asperflavin ribofuranoside)

SMILES for NP0006412 (Asperflavin ribofuranoside)

INCHI for NP0006412 (Asperflavin ribofuranoside)

Structure for NP0006412 (Asperflavin ribofuranoside)

3D Structure for NP0006412 (Asperflavin ribofuranoside)