NP-MRD: Showing NP-Card for Isovanilloylcatalpol (NP0073889)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 19:06:24 UTC

Updated at

2022-04-28 19:06:24 UTC

NP-MRD ID

NP0073889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovanilloylcatalpol

Description

(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Isovanilloylcatalpol is found in Veronica turrilliana. Based on a literature review very few articles have been published on (1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]Dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221062D          

 36 40  0  0  1  0            999 V2000
    2.9411    2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3452    1.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5531    1.7538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3569    2.5551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9527    3.1258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7448    2.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    3.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    4.4977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1561    5.2990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7519    5.8696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5440    5.6389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7403    4.8376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1444    4.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5323    4.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282    5.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398    6.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    6.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    5.5297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    2.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2219    1.8525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8517    1.3196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7907    0.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727    0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    0.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4118   -0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -2.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -1.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -3.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9109   -3.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -2.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    2.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5088    3.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180    3.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  4 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 20 34  1  6  0  0  0
 19 34  1  0  0  0  0
 19 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    8.3996    2.4469   -2.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5572    1.6490   -1.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4353    1.0930   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532    1.2880   -1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    0.7235   -0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968   -0.0563    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634   -0.6712    0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2728   -1.3726    1.8874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -0.5135    0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -1.1237    1.1483 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6754   -0.2010    1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1090    1.1949    1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487    2.0961    1.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    1.7103    1.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666    0.4637    1.0640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4719    0.7938    0.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    0.3504    0.2803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1361   -0.4573   -0.7866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4189   -0.9813   -0.6107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5533   -2.1120   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8062   -2.6941   -1.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3907    0.1320   -0.9320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5725    0.0114   -0.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493    1.4785   -0.7478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1425    1.9239   -1.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424    1.5135    0.3649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4167    1.5365    1.5840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471   -0.1601    0.5191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3780   -1.5785    0.1302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6165   -2.3713   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -3.7243   -0.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868   -1.8251   -0.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -2.1136    0.3215 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4804   -0.2482    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832    0.3082    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793    0.0914    0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431    3.2458   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3859    2.9412   -3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1818    1.8054   -3.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0134    1.8945   -2.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0315    0.8773   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229   -1.7065    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -0.5869    2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    1.4390    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    3.1610    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -0.1328    1.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -0.2114    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5169   -1.3746    0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4712   -1.7031   -2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7539   -2.8433   -1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0621   -2.8655   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6780    0.0051   -2.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4295    0.1982    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5732    2.1852   -0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    2.6639   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1748    2.4602    0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8282    1.2396    2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673    0.5184   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291   -2.1609   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3254   -2.2225    0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -3.8625   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0617   -3.2008    0.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6309   -0.8635    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6819    0.4988    0.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 35  2  0
 35 36  1  0
 35 34  1  0
 34  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 33  1  0
 33 32  1  0
 32 29  1  0
 29 30  1  6
 30 31  1  0
 29 28  1  0
 28 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  4  3  1  0
 11 10  1  0
 26 17  1  0
 29 33  1  0
 15 28  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 36 64  1  0
 34 63  1  0
  5 41  1  0
  4 40  1  0
 10 42  1  1
 33 62  1  6
 30 59  1  0
 30 60  1  0
 31 61  1  0
 28 58  1  6
 11 43  1  1
 12 44  1  0
 13 45  1  0
 15 46  1  1
 17 47  1  1
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  6
 23 53  1  0
 24 54  1  1
 25 55  1  0
 26 56  1  6
 27 57  1  0
M  END


  Mrv1652304282221062D          

 36 40  0  0  1  0            999 V2000
    2.9411    2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3452    1.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5531    1.7538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3569    2.5551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9527    3.1258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7448    2.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    3.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    4.4977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1561    5.2990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7519    5.8696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5440    5.6389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7403    4.8376    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1444    4.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5323    4.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282    5.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398    6.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    6.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    5.5297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    2.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2219    1.8525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8517    1.3196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7907    0.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727    0.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    0.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4118   -0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -2.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -1.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -3.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9109   -3.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -2.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    2.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5088    3.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180    3.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  4 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 20 34  1  6  0  0  0
 19 34  1  0  0  0  0
 19 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1)C(=O)O[C@@H]1[C@@H]2O[C@]2(CO)[C@@H]2[C@@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O13/c1-31-12-3-2-9(6-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10-,13+,14+,15+,16-,17+,18-,19-,21-,22-,23+/m0/s1

> <INCHI_KEY>
DSVKJARKMOAAKJ-DGHUALLOSA-N

> <FORMULA>
C23H28O13

> <MOLECULAR_WEIGHT>
512.464

> <EXACT_MASS>
512.152990962

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.683445540773405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-1.3977403483333328

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.204173680192747

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5964585226654

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601929344

> <JCHEM_POLAR_SURFACE_AREA>
197.13

> <JCHEM_REFRACTIVITY>
115.45759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.490   3.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.378   2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.899   3.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.533   4.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.645   5.835   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.124   5.404   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.279   7.331   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.391   8.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.025   9.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.137  10.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.615  10.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.982   9.030   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.870   7.965   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.460   8.600   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.573   9.665   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.728  11.591   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.771  12.452   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.546  10.322   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.997   4.883   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.414   3.458   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.590   2.463   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.476   0.927   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.749   0.061   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.136   0.730   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.635  -1.475   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.908  -2.341   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.795  -3.877   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.408  -4.546   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.135  -3.680   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.248  -2.144   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.294  -6.082   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.567  -6.949   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.068  -4.744   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.529   4.675   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.950   6.423   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.407   7.151   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    4   20   34   35                                             
CONECT   20   19   21   34                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28   32                                                       
CONECT   32   31                                                            
CONECT   33   27                                                            
CONECT   34   20   19                                                       
CONECT   35   19   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4S,5S,6S,10S)-2-(Hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0,]dec-7-en-5-yl 3-hydroxy-4-methoxybenzoic acid	Generator

Chemical Formula

C₂₃H₂₈O₁₃

Average Mass

512.4640 Da

Monoisotopic Mass

512.15299 Da

IUPAC Name

(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate

Traditional Name

(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-5-yl 3-hydroxy-4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C(=O)O[C@@H]1[C@@H]2O[C@]2(CO)[C@@H]2[C@@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H28O13/c1-31-12-3-2-9(6-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10-,13+,14+,15+,16-,17+,18-,19-,21-,22-,23+/m0/s1

InChI Key

DSVKJARKMOAAKJ-DGHUALLOSA-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
Veronica turrilliana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
M-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
O-glycosyl compound
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	-0.36	ALOGPS
logP	-1.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	115.46 m³·mol⁻¹	ChemAxon
Polarizability	49.68 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

163030616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isovanilloylcatalpol (NP0073889)

MOL for NP0073889 (Isovanilloylcatalpol)

3D MOL for NP0073889 (Isovanilloylcatalpol)

3D SDF for NP0073889 (Isovanilloylcatalpol)

3D-SDF for NP0073889 (Isovanilloylcatalpol)

PDB for NP0073889 (Isovanilloylcatalpol)

3D PDB for NP0073889 (Isovanilloylcatalpol)

SMILES for NP0073889 (Isovanilloylcatalpol)

INCHI for NP0073889 (Isovanilloylcatalpol)

Structure for NP0073889 (Isovanilloylcatalpol)

3D Structure for NP0073889 (Isovanilloylcatalpol)