NP-MRD: Showing NP-Card for 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+ (NP0038284)

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Record Information

Version

2.0

Created at

2021-06-20 21:00:44 UTC

Updated at

2021-06-30 00:10:59 UTC

NP-MRD ID

NP0038284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+

Provided By

JEOL Database JEOL Logo

Description

(2R,3R,4S,5S,6R)-2-{[(3R,3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+ is found in Ainsliaea fragrans. 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+ was first documented in 2009 (Wang, H., et al.). Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-{[(3R,3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123003D          

 78 82  0  0  0  0            999 V2000
    1.6621    1.2520    4.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    1.8641    4.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    3.3605    4.3001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5141    4.1229    2.9807 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4438    5.5239    3.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    3.8027    1.9719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5276    4.6292    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8588    4.9044    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    3.7448   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    4.0753   -1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    2.4726    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    2.3626    1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4031    1.3805    2.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4894   -0.0339    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -0.4034    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9197   -6.8080    2.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4592   -5.3938    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7779   -5.5754    3.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5140   -5.3436    3.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -6.6957    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -3.9213    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169   -5.1030   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -3.4148   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9258   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -1.2713    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.6711   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    1.7382   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6 12  1  0  0  0  0
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  9  7  1  0  0  0  0
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  9 10  2  0  0  0  0
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  2  1  2  3  0  0  0
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 23 20  1  0  0  0  0
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M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
    1.6621    1.2520    4.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    1.8641    4.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    3.3605    4.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    4.1229    2.9807 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4438    5.5239    3.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    3.8027    1.9719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5276    4.6292    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8588    4.9044    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    3.7448   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    4.0753   -1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    2.4726    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    2.3626    1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4031    1.3805    2.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4894   -0.0339    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -0.4034    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -0.9977    2.6745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209   -0.9781    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -2.1546    1.5532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2281   -3.2021    2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -4.4155    1.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7110   -5.5328    2.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9197   -6.8080    2.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940   -4.1967    1.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4592   -5.3938    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8944   -3.0763    0.1403 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.3730    4.2157   -5.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0735    4.6554   -5.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5140   -5.3436    3.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3154   -3.4148   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9258   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -1.2713    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.6711   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    1.7382   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    2.9079   -4.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    4.6365   -6.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510    5.7551   -5.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    4.3347   -3.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    2.7368   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.6027    4.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1720   -0.7144    4.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.6045    4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
 25 26  1  0
 27 28  1  0
 40 33  1  0
 42  2  1  0
 13 12  1  0
 36 37  1  0
  2  3  1  0
 33 34  2  0
  3  4  1  0
  6  4  1  0
 13 42  1  0
 38 39  1  0
 34 35  1  0
 33 32  1  0
 36 38  1  0
 32 31  2  0
 42 41  1  0
 41 16  1  0
 16 14  1  0
 14 13  1  0
  6 12  1  0
 31 29  1  0
 38 40  2  0
 29 30  2  0
 35 36  2  0
 12 11  1  0
 11  9  1  0
  9  7  1  0
  6  7  1  0
 29 28  1  0
  9 10  2  0
 18 27  1  0
  2  1  2  3
 27 25  1  0
  4  5  1  0
 25 23  1  0
 42 78  1  1
 23 20  1  0
 13 55  1  1
 20 19  1  0
  7  8  1  0
 16 17  1  0
 19 18  1  0
 14 15  2  3
 21 22  1  0
 20 21  1  0
 18 17  1  0
 34 71  1  0
 35 72  1  0
 40 75  1  0
 32 70  1  0
 31 69  1  0
 37 73  1  0
 39 74  1  0
 18 59  1  6
 23 64  1  1
 24 65  1  0
 25 66  1  6
 26 67  1  0
 27 68  1  1
 21 61  1  0
 21 62  1  0
 20 60  1  6
  3 45  1  0
  3 46  1  0
  4 47  1  6
 41 76  1  0
 41 77  1  0
 16 58  1  1
  6 49  1  1
 12 54  1  6
  7 50  1  1
  1 43  1  0
  1 44  1  0
  5 48  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
 15 56  1  0
 15 57  1  0
 22 63  1  0
M  END


  Mrv1652306202123003D          

 78 82  0  0  0  0            999 V2000
    1.6621    1.2520    4.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    1.8641    4.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    3.3605    4.3001 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5141    4.1229    2.9807 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4438    5.5239    3.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    3.8027    1.9719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5276    4.6292    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8588    4.9044    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    3.7448   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    4.0753   -1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    2.4726    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    2.3626    1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4031    1.3805    2.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4894   -0.0339    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -0.4034    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -0.9977    2.6745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209   -0.9781    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -2.1546    1.5532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2281   -3.2021    2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -4.4155    1.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7110   -5.5328    2.9057 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9197   -6.8080    2.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940   -4.1967    1.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4592   -5.3938    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8944   -3.0763    0.1403 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334   -2.8731   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -1.8083    0.7328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8106   -0.9213   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -0.1496   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -0.2150   -0.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    0.7744   -1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338    1.6917   -2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    2.6813   -3.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    3.2361   -4.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    4.2157   -5.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0735    4.6554   -5.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611    5.6219   -5.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1318   -4.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    4.6339   -3.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075    3.1410   -3.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -0.3524    4.0428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8399    1.1727    3.8091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5600    1.8105    4.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    0.1788    4.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    3.7117    4.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5495    3.6319    4.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    3.9236    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    5.7491    3.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608    4.0379    2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    5.5656    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7827    5.3771   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    3.9821   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    5.5822    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    1.9782    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    1.7415    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342    0.3219    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224   -1.4395    0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -2.0094    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -2.4388    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8916   -4.7131    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -5.5754    3.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5140   -5.3436    3.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -6.6957    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -3.9213    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169   -5.1030   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -3.4148   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9258   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -1.2713    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.6711   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    1.7382   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    2.9079   -4.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    4.6365   -6.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510    5.7551   -5.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    4.3347   -3.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    2.7368   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.6027    4.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1720   -0.7144    4.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.6045    4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 40 33  1  0  0  0  0
 42  2  1  0  0  0  0
 13 12  1  0  0  0  0
 36 37  1  0  0  0  0
  2  3  1  0  0  0  0
 33 34  2  0  0  0  0
  3  4  1  0  0  0  0
  6  4  1  0  0  0  0
 13 42  1  0  0  0  0
 38 39  1  0  0  0  0
 34 35  1  0  0  0  0
 33 32  1  0  0  0  0
 36 38  1  0  0  0  0
 32 31  2  0  0  0  0
 42 41  1  0  0  0  0
 41 16  1  0  0  0  0
 16 14  1  0  0  0  0
 14 13  1  0  0  0  0
  6 12  1  0  0  0  0
 31 29  1  0  0  0  0
 38 40  2  0  0  0  0
 29 30  2  0  0  0  0
 35 36  2  0  0  0  0
 12 11  1  0  0  0  0
 11  9  1  0  0  0  0
  9  7  1  0  0  0  0
  6  7  1  0  0  0  0
 29 28  1  0  0  0  0
  9 10  2  0  0  0  0
 18 27  1  0  0  0  0
  2  1  2  3  0  0  0
 27 25  1  0  0  0  0
  4  5  1  0  0  0  0
 25 23  1  0  0  0  0
 42 78  1  1  0  0  0
 23 20  1  0  0  0  0
 13 55  1  1  0  0  0
 20 19  1  0  0  0  0
  7  8  1  0  0  0  0
 16 17  1  0  0  0  0
 19 18  1  0  0  0  0
 14 15  2  3  0  0  0
 21 22  1  0  0  0  0
 20 21  1  0  0  0  0
 18 17  1  0  0  0  0
 34 71  1  0  0  0  0
 35 72  1  0  0  0  0
 40 75  1  0  0  0  0
 32 70  1  0  0  0  0
 31 69  1  0  0  0  0
 37 73  1  0  0  0  0
 39 74  1  0  0  0  0
 18 59  1  6  0  0  0
 23 64  1  1  0  0  0
 24 65  1  0  0  0  0
 25 66  1  6  0  0  0
 26 67  1  0  0  0  0
 27 68  1  1  0  0  0
 21 61  1  0  0  0  0
 21 62  1  0  0  0  0
 20 60  1  6  0  0  0
  3 45  1  0  0  0  0
  3 46  1  0  0  0  0
  4 47  1  6  0  0  0
 41 76  1  0  0  0  0
 41 77  1  0  0  0  0
 16 58  1  1  0  0  0
  6 49  1  1  0  0  0
 12 54  1  6  0  0  0
  7 50  1  1  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  5 48  1  0  0  0  0
  8 51  1  0  0  0  0
  8 52  1  0  0  0  0
  8 53  1  0  0  0  0
 15 56  1  0  0  0  0
 15 57  1  0  0  0  0
 22 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]2([H])[C@]([H])(O[C@]3([H])C(=C([H])[H])[C@]4([H])[C@@]5([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]5([H])[C@@]([H])(O[H])C([H])([H])C(=C([H])[H])[C@]4([H])C3([H])[H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O12/c1-12-8-19(34)24-14(3)29(38)42-27(24)23-13(2)20(10-16(12)23)39-30-28(26(37)25(36)21(11-31)40-30)41-22(35)7-5-15-4-6-17(32)18(33)9-15/h4-7,9,14,16,19-21,23-28,30-34,36-37H,1-2,8,10-11H2,3H3/b7-5+/t14-,16+,19+,20+,21-,23+,24-,25-,26+,27-,28-,30-/m1/s1

> <INCHI_KEY>
GTXJTCMGBHOAQX-HBNJJJMWSA-N

> <FORMULA>
C30H36O12

> <MOLECULAR_WEIGHT>
588.606

> <EXACT_MASS>
588.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.876642089737665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3R,3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.0135520750000002

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.349353714503227

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208453902391417

> <JCHEM_PKA_STRONGEST_BASIC>
-2.899596503036446

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
145.19700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3R,3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-octahydro-3H-azuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
    1.6621    1.2520    4.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    1.8641    4.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    3.3605    4.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    4.1229    2.9807 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4438    5.5239    3.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    3.8027    1.9719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5276    4.6292    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8588    4.9044    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    3.7448   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    4.0753   -1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    2.4726    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    2.3626    1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4031    1.3805    2.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4894   -0.0339    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -0.4034    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -0.9977    2.6745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209   -0.9781    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -2.1546    1.5532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2281   -3.2021    2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -4.4155    1.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7110   -5.5328    2.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9197   -6.8080    2.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940   -4.1967    1.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4592   -5.3938    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8944   -3.0763    0.1403 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334   -2.8731   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -1.8083    0.7328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8106   -0.9213   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -0.1496   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -0.2150   -0.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    0.7744   -1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338    1.6917   -2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    2.6813   -3.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    3.2361   -4.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    4.2157   -5.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0735    4.6554   -5.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611    5.6219   -5.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1318   -4.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    4.6339   -3.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075    3.1410   -3.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -0.3524    4.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399    1.1727    3.8091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5600    1.8105    4.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    0.1788    4.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    3.7117    4.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5495    3.6319    4.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    3.9236    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    5.7491    3.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608    4.0379    2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    5.5656    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7827    5.3771   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    3.9821   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    5.5822    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    1.9782    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    1.7415    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342    0.3219    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224   -1.4395    0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -2.0094    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -2.4388    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8916   -4.7131    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -5.5754    3.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5140   -5.3436    3.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -6.6957    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -3.9213    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169   -5.1030   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -3.4148   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9258   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -1.2713    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.6711   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    1.7382   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    2.9079   -4.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    4.6365   -6.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510    5.7551   -5.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    4.3347   -3.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    2.7368   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.6027    4.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1720   -0.7144    4.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.6045    4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  0
 25 26  1  0
 27 28  1  0
 40 33  1  0
 42  2  1  0
 13 12  1  0
 36 37  1  0
  2  3  1  0
 33 34  2  0
  3  4  1  0
  6  4  1  0
 13 42  1  0
 38 39  1  0
 34 35  1  0
 33 32  1  0
 36 38  1  0
 32 31  2  0
 42 41  1  0
 41 16  1  0
 16 14  1  0
 14 13  1  0
  6 12  1  0
 31 29  1  0
 38 40  2  0
 29 30  2  0
 35 36  2  0
 12 11  1  0
 11  9  1  0
  9  7  1  0
  6  7  1  0
 29 28  1  0
  9 10  2  0
 18 27  1  0
  2  1  2  3
 27 25  1  0
  4  5  1  0
 25 23  1  0
 42 78  1  1
 23 20  1  0
 13 55  1  1
 20 19  1  0
  7  8  1  0
 16 17  1  0
 19 18  1  0
 14 15  2  3
 21 22  1  0
 20 21  1  0
 18 17  1  0
 34 71  1  0
 35 72  1  0
 40 75  1  0
 32 70  1  0
 31 69  1  0
 37 73  1  0
 39 74  1  0
 18 59  1  6
 23 64  1  1
 24 65  1  0
 25 66  1  6
 26 67  1  0
 27 68  1  1
 21 61  1  0
 21 62  1  0
 20 60  1  6
  3 45  1  0
  3 46  1  0
  4 47  1  6
 41 76  1  0
 41 77  1  0
 16 58  1  1
  6 49  1  1
 12 54  1  6
  7 50  1  1
  1 43  1  0
  1 44  1  0
  5 48  1  0
  8 51  1  0
  8 52  1  0
  8 53  1  0
 15 56  1  0
 15 57  1  0
 22 63  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.662   1.252   4.313  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.480   1.864   4.126  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.386   3.361   4.300  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.514   4.123   2.981  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.444   5.524   3.261  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.590   3.803   1.972  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.528   4.629   0.681  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.859   4.904   0.110  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.272   3.745  -0.273  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.711   4.075  -1.366  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.325   2.473   0.203  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.627   2.363   1.465  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.403   1.381   2.372  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.489  -0.034   1.803  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.253  -0.403   0.763  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.741  -0.998   2.675  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.621  -0.978   2.274  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.998  -2.155   1.553  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.228  -3.202   2.491  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.637  -4.415   1.856  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.711  -5.533   2.906  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.920  -6.808   2.309  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.994  -4.197   1.181  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.459  -5.394   0.546  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.894  -3.076   0.140  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.233  -2.873  -0.349  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.260  -1.808   0.733  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.811  -0.921  -0.329  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.741  -0.150  -0.928  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.945  -0.215  -0.746  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.044   0.774  -1.840  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.734   1.692  -2.535  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.122   2.681  -3.437  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.900   3.236  -4.466  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.373   4.216  -5.315  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.073   4.655  -5.118  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.561   5.622  -5.934  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.296   4.132  -4.091  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.966   4.634  -3.924  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.808   3.141  -3.260  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.905  -0.352   4.043  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.840   1.173   3.809  0.00  0.00           C+0
HETATM   43  H   UNK     0       2.560   1.811   4.564  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.792   0.179   4.218  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.169   3.712   4.986  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.550   3.632   4.807  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.500   3.924   2.544  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.189   5.749   3.846  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.561   4.038   2.435  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.081   5.566   0.810  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.783   5.377  -0.875  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.436   3.982  -0.017  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.429   5.582   0.752  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.377   1.978   1.242  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.439   1.742   2.462  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.834   0.322   0.200  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.322  -1.440   0.447  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.164  -2.009   2.680  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.186  -2.439   0.869  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.892  -4.713   1.106  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.778  -5.575   3.478  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.514  -5.344   3.627  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.632  -6.696   1.642  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.747  -3.921   1.932  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.217  -5.103  -0.007  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.315  -3.415  -0.728  0.00  0.00           H+0
HETATM   67  H   UNK     0       4.354  -1.926  -0.576  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.980  -1.271   1.365  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.968   0.671  -1.904  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.819   1.738  -2.446  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.925   2.908  -4.624  0.00  0.00           H+0
HETATM   72  H   UNK     0       2.974   4.636  -6.115  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.351   5.755  -5.604  0.00  0.00           H+0
HETATM   74  H   UNK     0      -1.316   4.335  -3.054  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.183   2.737  -2.473  0.00  0.00           H+0
HETATM   76  H   UNK     0      -1.898  -0.603   4.441  0.00  0.00           H+0
HETATM   77  H   UNK     0      -0.172  -0.714   4.770  0.00  0.00           H+0
HETATM   78  H   UNK     0      -1.565   1.605   4.516  0.00  0.00           H+0
CONECT    1    2   43   44                                                  
CONECT    2   42    3    1                                                  
CONECT    3    2    4   45   46                                             
CONECT    4    3    6    5   47                                             
CONECT    5    4   48                                                       
CONECT    6    4   12    7   49                                             
CONECT    7    9    6    8   50                                             
CONECT    8    7   51   52   53                                             
CONECT    9   11    7   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9                                                       
CONECT   12   13    6   11   54                                             
CONECT   13   12   42   14   55                                             
CONECT   14   16   13   15                                                  
CONECT   15   14   56   57                                                  
CONECT   16   41   14   17   58                                             
CONECT   17   16   18                                                       
CONECT   18   27   19   17   59                                             
CONECT   19   20   18                                                       
CONECT   20   23   19   21   60                                             
CONECT   21   22   20   61   62                                             
CONECT   22   21   63                                                       
CONECT   23   24   25   20   64                                             
CONECT   24   23   65                                                       
CONECT   25   26   27   23   66                                             
CONECT   26   25   67                                                       
CONECT   27   28   18   25   68                                             
CONECT   28   27   29                                                       
CONECT   29   31   30   28                                                  
CONECT   30   29                                                            
CONECT   31   32   29   69                                                  
CONECT   32   33   31   70                                                  
CONECT   33   40   34   32                                                  
CONECT   34   33   35   71                                                  
CONECT   35   34   36   72                                                  
CONECT   36   37   38   35                                                  
CONECT   37   36   73                                                       
CONECT   38   39   36   40                                                  
CONECT   39   38   74                                                       
CONECT   40   33   38   75                                                  
CONECT   41   42   16   76   77                                             
CONECT   42    2   13   41   78                                             
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    3                                                            
CONECT   46    3                                                            
CONECT   47    4                                                            
CONECT   48    5                                                            
CONECT   49    6                                                            
CONECT   50    7                                                            
CONECT   51    8                                                            
CONECT   52    8                                                            
CONECT   53    8                                                            
CONECT   54   12                                                            
CONECT   55   13                                                            
CONECT   56   15                                                            
CONECT   57   15                                                            
CONECT   58   16                                                            
CONECT   59   18                                                            
CONECT   60   20                                                            
CONECT   61   21                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   26                                                            
CONECT   68   27                                                            
CONECT   69   31                                                            
CONECT   70   32                                                            
CONECT   71   34                                                            
CONECT   72   35                                                            
CONECT   73   37                                                            
CONECT   74   39                                                            
CONECT   75   40                                                            
CONECT   76   41                                                            
CONECT   77   41                                                            
CONECT   78   42                                                            
MASTER        0    0    0    0    0    0    0    0   78    0  164    0
END

RDKit          3D

78 82  0  0  0  0  0  0  0  0999 V2000
    1.6621    1.2520    4.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799    1.8641    4.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3859    3.3605    4.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    4.1229    2.9807 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4438    5.5239    3.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898    3.8027    1.9719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5276    4.6292    0.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8588    4.9044    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720    3.7448   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    4.0753   -1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    2.4726    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265    2.3626    1.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4031    1.3805    2.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4894   -0.0339    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -0.4034    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -0.9977    2.6745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209   -0.9781    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -2.1546    1.5532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2281   -3.2021    2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -4.4155    1.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7110   -5.5328    2.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9197   -6.8080    2.3088 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940   -4.1967    1.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4592   -5.3938    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8944   -3.0763    0.1403 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334   -2.8731   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -1.8083    0.7328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8106   -0.9213   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -0.1496   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -0.2150   -0.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    0.7744   -1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338    1.6917   -2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1218    2.6813   -3.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    3.2361   -4.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    4.2157   -5.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0735    4.6554   -5.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611    5.6219   -5.9337 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    4.1318   -4.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    4.6339   -3.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075    3.1410   -3.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -0.3524    4.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399    1.1727    3.8091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5600    1.8105    4.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    0.1788    4.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5495    3.6319    4.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    3.9236    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    5.7491    3.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608    4.0379    2.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813    5.5656    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7827    5.3771   -0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    3.9821   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    5.5822    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773    1.9782    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    1.7415    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342    0.3219    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224   -1.4395    0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -2.0094    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -2.4388    0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8916   -4.7131    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -5.5754    3.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5140   -5.3436    3.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -6.6957    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -3.9213    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169   -5.1030   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -3.4148   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -1.9258   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -1.2713    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.6711   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187    1.7382   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    2.9079   -4.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    4.6365   -6.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510    5.7551   -5.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    4.3347   -3.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    2.7368   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.6027    4.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1720   -0.7144    4.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.6045    4.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,5S,6R)-2-{[(3R,3ar,4S,6ar,8S,9ar,9BR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₀H₃₆O₁₂

Average Mass

588.6060 Da

Monoisotopic Mass

588.22068 Da

IUPAC Name

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(3R,3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-octahydro-3H-azuleno[4,5-b]furan-8-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]2([H])[C@]([H])(O[C@]3([H])C(=C([H])[H])[C@]4([H])[C@@]5([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@]5([H])[C@@]([H])(O[H])C([H])([H])C(=C([H])[H])[C@]4([H])C3([H])[H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1O[H]

InChI Identifier

InChI=1S/C30H36O12/c1-12-8-19(34)24-14(3)29(38)42-27(24)23-13(2)20(10-16(12)23)39-30-28(26(37)25(36)21(11-31)40-30)41-22(35)7-5-15-4-6-17(32)18(33)9-15/h4-7,9,14,16,19-21,23-28,30-34,36-37H,1-2,8,10-11H2,3H3/b7-5+/t14-,16+,19+,20+,21-,23+,24-,25-,26+,27-,28-,30-/m1/s1

InChI Key

GTXJTCMGBHOAQX-HBNJJJMWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ainsliaea fragrans	JEOL database	Wang, H., et al, Chem. Pharm. Bull. 57, 597 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Fatty acyl
Benzenoid
Monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Primary alcohol
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.95	ALOGPS
logP	1.01	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	145.2 m³·mol⁻¹	ChemAxon
Polarizability	59.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

44130031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, H., et al. (2009). Wang, H., et al, Chem. Pharm. Bull. 57, 597 (2009). Chem. Pharm. Bull..

Showing NP-Card for 2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+ (NP0038284)

MOL for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

3D MOL for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

3D SDF for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

3D-SDF for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

PDB for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

3D PDB for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

SMILES for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

INCHI for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

Structure for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)

3D Structure for NP0038284 (2'-O-E-caffeoyl-8alpha-hydroxy-11alpha,13-dihydro-3beta-O-beta-D-glucozal+)