NP-MRD: Showing NP-Card for 19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid (NP0204089)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 23:42:01 UTC

Updated at

2022-09-04 23:42:02 UTC

NP-MRD ID

NP0204089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

Description

19-Ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid is found in Simira rubescens and Stenostomum acreanum. Based on a literature review very few articles have been published on 19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201422D          

 38 43  0  0  0  0            999 V2000
    4.1805   -2.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -2.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662   -3.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444   -3.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165   -4.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -3.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -3.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106   -2.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -1.8688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999   -2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -1.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  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  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 27 35  1  0  0  0  0
 30 35  1  0  0  0  0
 28 36  1  0  0  0  0
 21 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 19 38  1  0  0  0  0
  3 38  1  0  0  0  0
M  END

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
    1.4839    2.8781    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166    2.0850   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636    0.6191   -0.1050 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8184    0.2032    0.7635 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0656    0.5100    0.2789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8402   -0.6105    0.0107 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0683   -0.6410   -1.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9523   -1.5295   -1.8386 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1835   -2.6868   -2.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -2.1843   -3.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9915   -1.9932   -0.8603 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4071   -3.0243   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294   -0.8065    0.0159 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4431   -0.9766    0.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0913   -0.4949    0.8350 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2723    0.7364    1.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    0.6125    2.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    0.1866    2.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -0.0119    1.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317   -0.4795    2.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -1.1338    1.6748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1918   -0.8640    2.0750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3867   -1.2310    3.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605   -1.7323    4.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6621   -0.9962    4.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068    0.5960    1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.8290    0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703    0.0276   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    0.5014   -1.6230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667    1.5619   -1.7380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5120    2.4019   -2.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3976    3.4515   -2.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9658    3.6699   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6344    2.8464   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7479    1.8053   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449   -1.1338    0.2765 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1872   -1.1134   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487    0.1935    0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2582    2.4647    0.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    3.9754    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471    2.5683   -0.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.1822   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.9365    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2418   -1.5062    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4924   -1.0346   -2.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046   -3.3916   -2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176   -3.2522   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -2.8067   -3.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8765   -2.3678   -1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1765   -3.6282    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5135    0.0473   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274   -0.6114    0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386   -1.2578    1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951    1.5007    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    0.0035    3.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649   -1.2588    3.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920    0.3538    3.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8652   -1.4900    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4775   -1.4890    3.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5828    0.7866    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066    1.2956    2.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    0.0705   -2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    2.2600   -3.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6681    4.1149   -3.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6580    4.5049   -1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0611    2.9987    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -2.0983   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -1.9632    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0508   -1.0932   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4086    0.9866    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 28 36  1  0
 36 37  1  0
 37 38  1  0
 38  3  1  0
  3  2  1  0
  2  1  2  3
 22 23  1  0
 23 25  1  0
 23 24  2  0
  6 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  8  1  0
  3  4  1  0
 38 19  1  0
 36 21  1  0
 35 27  1  0
 35 30  1  0
 10 48  1  0
  9 46  1  0
  9 47  1  0
  8 45  1  6
  6 44  1  1
  4 43  1  1
 18 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  6
 26 60  1  0
 26 61  1  0
 29 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
 34 66  1  0
 36 67  1  6
 37 68  1  0
 37 69  1  0
 38 70  1  1
  3 42  1  6
  2 41  1  0
  1 39  1  0
  1 40  1  0
 25 59  1  0
 15 53  1  1
 16 54  1  0
 13 51  1  6
 14 52  1  0
 11 49  1  6
 12 50  1  0
M  END


  Mrv1652309052201422D          

 38 43  0  0  0  0            999 V2000
    4.1805   -2.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -2.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662   -3.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444   -3.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165   -4.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271   -4.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -3.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -3.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106   -2.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -1.8688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999   -2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -1.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  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  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 27 35  1  0  0  0  0
 30 35  1  0  0  0  0
 28 36  1  0  0  0  0
 21 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 19 38  1  0  0  0  0
  3 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C3CN4C(CC5=C(NC6=CC=CC=C56)C4CC3C2C=C)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O9/c1-2-13-15-7-18-21-16(14-5-3-4-6-17(14)28-21)8-19(25(34)35)29(18)9-12(15)11-36-26(13)38-27-24(33)23(32)22(31)20(10-30)37-27/h2-6,11,13,15,18-20,22-24,26-28,30-33H,1,7-10H2,(H,34,35)

> <INCHI_KEY>
YWKCKNNZOGDZTJ-UHFFFAOYSA-N

> <FORMULA>
C27H32N2O9

> <MOLECULAR_WEIGHT>
528.558

> <EXACT_MASS>
528.210780618

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.30589647105294

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

> <JCHEM_LOGP>
-2.1492335390486126

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.206668760770395

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.556176363704151

> <JCHEM_PKA_STRONGEST_BASIC>
6.847090887702533

> <JCHEM_POLAR_SURFACE_AREA>
164.94

> <JCHEM_REFRACTIVITY>
132.84949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.804  -4.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.265  -5.248   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.752  -5.535   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.244  -6.989   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.269  -7.276   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.777  -8.730   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.291  -9.017   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.275  -6.109   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.788  -6.396   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.767  -4.655   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.772  -3.488   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.747  -4.368   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.255  -2.914   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.762  -7.869   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.295 -12.249   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.300 -13.416   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.782 -12.536   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   38                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   36                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   27   30                                                  
CONECT   36   28   21   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   19    3                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
19-Ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8,15-pentaene-12-carboxylate	Generator

Chemical Formula

C₂₇H₃₂N₂O₉

Average Mass

528.5580 Da

Monoisotopic Mass

528.21078 Da

IUPAC Name

19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

Traditional Name

19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=C3CN4C(CC5=C(NC6=CC=CC=C56)C4CC3C2C=C)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H32N2O9/c1-2-13-15-7-18-21-16(14-5-3-4-6-17(14)28-21)8-19(25(34)35)29(18)9-12(15)11-36-26(13)38-27-24(33)23(32)22(31)20(10-30)37-27/h2-6,11,13,15,18-20,22-24,26-28,30-33H,1,7-10H2,(H,34,35)

InChI Key

YWKCKNNZOGDZTJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Simira rubescens	LOTUS Database	35616633
Stenostomum acreanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Aralkylamine
Monosaccharide
Oxane
Piperidine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Amino acid
Azacycle
Polyol
Oxacycle
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Amine
Alcohol
Organic nitrogen compound
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	-2.1	ChemAxon
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	6.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.85 m³·mol⁻¹	ChemAxon
Polarizability	55.31 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

85110573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid (NP0204089)

MOL for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

3D MOL for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

3D SDF for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

3D-SDF for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

PDB for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

3D PDB for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

SMILES for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

INCHI for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

Structure for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)

3D Structure for NP0204089 (19-ethenyl-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaene-12-carboxylic acid)