NP-MRD: Showing NP-Card for Glabraoside A (NP0082013)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 03:03:48 UTC

Updated at

2022-04-29 03:03:48 UTC

NP-MRD ID

NP0082013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glabraoside A

Description

(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),8-trien-12-one belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Glabraoside A is found in Rhizophora stylosa . Based on a literature review very few articles have been published on (4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1(10),2(7),8-trien-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205032D          

 43 48  0  0  1  0            999 V2000
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  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
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  1  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
  8 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
  4 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  1 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 40 42  1  0  0  0  0
 39 43  1  0  0  0  0
M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
   -3.2164   -3.2661   -1.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123   -2.0303   -2.0473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1663   -0.8740   -1.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300   -0.5843   -0.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1296    0.4469   -0.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559    0.1248    0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0075    1.0522    1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    0.7301    2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1729    0.9815    3.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639    1.5323    4.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749    0.6823    4.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4322    0.1223    4.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -0.1206    2.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146    0.1794    1.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211   -0.0705    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    0.1729   -0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3989    1.3916   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826    2.5857   -0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    3.7178   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    3.6588   -2.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450    4.7534   -3.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2294    2.4860   -3.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.4198   -4.6290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801    1.3766   -2.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -0.7477    2.1002 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6967   -0.6989    0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1379    0.4232    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2237    0.4693   -1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630   -0.6210   -2.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480   -0.5784   -3.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4190   -1.7508   -1.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436   -2.8768   -2.2192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -1.7807   -0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502   -0.2627    2.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6458   -0.7054    4.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245   -1.5030    4.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267   -0.1517    4.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670   -0.1308    0.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3610    0.2694    1.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267   -1.2917   -0.1073 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1430   -2.2301    0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783   -1.9583   -1.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1412   -1.3512   -2.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1621   -4.0618   -2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153   -2.9740   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739   -3.7359   -0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392   -2.1318   -3.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000   -1.4636    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080   -0.9166    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0128    2.1112    1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780    0.9393    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    1.7494    5.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.8698    5.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893   -0.7097   -1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1461    2.6524    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    4.6493   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823    5.6488   -3.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    3.2453   -5.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2989    0.4810   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343   -1.8470    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4453    1.3335    0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    1.3587   -1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778    0.2641   -4.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -2.8281   -3.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814   -2.6954    0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8362    0.8502    2.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825   -0.7009    2.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7444    0.6637   -0.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1176    0.8940    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3552   -0.8701    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814   -1.8466    1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6400   -3.0179   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665   -1.9029   -3.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 24  2  0
 24 22  1  0
 22 23  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
 14 13  1  0
 13 12  2  0
 12 37  1  0
 37 35  1  0
 35 36  2  0
 35 34  1  0
 34 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  4 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42  2  1  0
 16  6  1  0
 18 17  1  0
 25 13  1  0
 33 26  1  0
  9  8  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  6
  4 48  1  1
  6 49  1  1
  7 50  1  0
  7 51  1  0
 16 54  1  6
 24 59  1  0
 23 58  1  0
 21 57  1  0
 19 56  1  0
 18 55  1  0
 34 66  1  0
 34 67  1  0
 25 60  1  6
 27 61  1  0
 28 62  1  0
 30 63  1  0
 32 64  1  0
 33 65  1  0
 11 53  1  0
 10 52  1  0
 38 68  1  6
 39 69  1  0
 40 70  1  1
 41 71  1  0
 42 72  1  1
 43 73  1  0
M  END


  Mrv1652304292205032D          

 43 48  0  0  1  0            999 V2000
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  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
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  1  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
  8 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 24 29  1  0  0  0  0
  4 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  1 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 40 42  1  0  0  0  0
 39 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2CC3=C(O[C@@H]2C2=CC(O)=C(O)C=C2)C2=C(OC(=O)C[C@@H]2C2=CC=C(O)C(O)=C2)C=C3O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O13/c1-11-25(37)26(38)27(39)30(40-11)42-22-8-15-18(33)10-21-24(29(15)43-28(22)13-3-5-17(32)20(35)7-13)14(9-23(36)41-21)12-2-4-16(31)19(34)6-12/h2-7,10-11,14,22,25-28,30-35,37-39H,8-9H2,1H3/t11-,14+,22+,25-,26+,27+,28+,30-/m0/s1

> <INCHI_KEY>
OKKMHZTVGJIQAP-BPOVIMKDSA-N

> <FORMULA>
C30H30O13

> <MOLECULAR_WEIGHT>
598.557

> <EXACT_MASS>
598.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.13711082495257

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
2.101362726666666

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.194867738658003

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.712715030362256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121825923590567

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999996

> <JCHEM_REFRACTIVITY>
145.8911

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.056   2.104   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.826   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.056   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.746   6.105   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.826   6.105   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.366   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.516  -5.898   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.056  -3.231   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.184  -5.898   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.104  -5.898   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22    8   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30    4                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    1   36                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   36                                                       
CONECT   42   40                                                            
CONECT   43   39                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₁₃

Average Mass

598.5570 Da

Monoisotopic Mass

598.16864 Da

IUPAC Name

(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

Traditional Name

(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-8-hydroxy-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2CC3=C(O[C@@H]2C2=CC(O)=C(O)C=C2)C2=C(OC(=O)C[C@@H]2C2=CC=C(O)C(O)=C2)C=C3O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H30O13/c1-11-25(37)26(38)27(39)30(40-11)42-22-8-15-18(33)10-21-24(29(15)43-28(22)13-3-5-17(32)20(35)7-13)14(9-23(36)41-21)12-2-4-16(31)19(34)6-12/h2-7,10-11,14,22,25-28,30-35,37-39H,8-9H2,1H3/t11-,14+,22+,25-,26+,27+,28+,30-/m0/s1

InChI Key

OKKMHZTVGJIQAP-BPOVIMKDSA-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
Rhizophora stylosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Catechin
Pyranoflavonoid
Linear 1,7-diphenylheptane skeleton
Pyranoneoflavonoid
Hydroxyflavonoid
Flavan-3-ol
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Neoflavonoid skeleton
Neoflavan
Flavan
Angular pyranocoumarin
Pyranocoumarin
Pyranochromene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
3,4-dihydrocoumarin
1-benzopyran
Benzopyran
Chromane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.99	ALOGPS
logP	2.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.71	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.89 m³·mol⁻¹	ChemAxon
Polarizability	57.14 Å³	ChemAxon
Number of Rings	6	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

154496657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glabraoside A (NP0082013)

MOL for NP0082013 (Glabraoside A)

3D MOL for NP0082013 (Glabraoside A)

3D SDF for NP0082013 (Glabraoside A)

3D-SDF for NP0082013 (Glabraoside A)

PDB for NP0082013 (Glabraoside A)

3D PDB for NP0082013 (Glabraoside A)

SMILES for NP0082013 (Glabraoside A)

INCHI for NP0082013 (Glabraoside A)

Structure for NP0082013 (Glabraoside A)

3D Structure for NP0082013 (Glabraoside A)