NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate (NP0330578)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 16:03:40 UTC

Updated at

2022-09-12 16:03:40 UTC

NP-MRD ID

NP0330578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

Description

(2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. (2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate is found in Mostuea brunonis. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218032D          

 39 44  0  0  1  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  1  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  2  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  2  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  2  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  1  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  2  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  1  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
    0.1337   -0.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -1.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -0.1574    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
    3.6304   -6.0907    0.0000 O   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
    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  2  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  1  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  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
 37 29  1  1  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  6  0  0  0
 22 39  1  0  0  0  0
  3 39  1  0  0  0  0
M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
    0.8235    3.1612   -1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031    1.8608   -1.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1645    1.2086   -0.8475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4948    0.6886   -1.2743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2343    0.1131   -0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139    0.7126    0.0204 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5103    1.2103    1.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499    1.9137    1.5336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3896    1.4422    2.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6306    1.5637    3.9272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6214    1.9858    0.4142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3301    3.0940   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971    0.7332   -0.3713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0169    0.1067   -0.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.2129   -0.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4498   -1.0992   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5204   -2.4719   -0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434   -3.4539   -2.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344   -2.8490    0.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -0.1345   -2.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162   -1.1936   -2.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -1.1277   -1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4526   -2.2470   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1452   -3.4030   -1.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -1.9019   -0.5173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -2.9195    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -2.4137    1.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356   -1.1214    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210   -0.2463   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2290    0.8188   -0.1651 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3304    0.6516    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4713    1.4196    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4830    0.9980    1.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862   -0.2081    2.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2529   -1.0029    2.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2286   -0.5714    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950   -0.5225   -0.6324 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0605    0.4285   -0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534    0.0097   -0.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6079    3.7199   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    3.6354   -2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    1.3016   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    1.8808    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    1.5799   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303    1.5976   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463    2.9756    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7445    0.4168    2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3123    2.0863    2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2702    0.6706    4.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6277    2.2378    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0345    3.2437   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7550    1.0178   -1.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7158    0.7030    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8004   -0.7263    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2451   -3.6220   -2.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7147   -2.9907   -3.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8792   -4.3905   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -2.0763   -2.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480   -3.5496   -0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7883   -3.6573    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -2.2684    2.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -3.1997    1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    1.6648   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5697    2.3753    0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3439    1.6226    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1418   -0.6083    2.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1484   -1.9623    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -0.3351   -1.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2241    0.5565    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355    1.4256   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032   -0.3454    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 20  1  0
 20 21  1  0
 21 22  2  0
 22 39  1  0
 39 38  1  0
 38 37  1  0
 37 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 25 23  1  0
 23 24  2  0
 39  3  1  0
  3  2  1  0
  2  1  2  3
  6 15  1  0
  3  4  1  0
 23 22  1  0
 29 37  1  0
 36 31  1  0
 36 28  1  0
 18 55  1  0
 18 56  1  0
 18 57  1  0
 15 54  1  1
 13 52  1  6
 14 53  1  0
 11 50  1  1
 12 51  1  0
  8 46  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  0
  6 45  1  6
  4 44  1  6
 21 58  1  0
 39 71  1  1
 38 69  1  0
 38 70  1  0
 37 68  1  6
 26 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 30 63  1  0
 32 64  1  0
 33 65  1  0
 34 66  1  0
 35 67  1  0
  3 43  1  1
  2 42  1  0
  1 40  1  0
  1 41  1  0
M  END


  Mrv1652309122218032D          

 39 44  0  0  1  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  1  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  2  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  2  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  2  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  1  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  2  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  1  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
    0.1337   -0.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -1.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -0.1574    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
    3.6304   -6.0907    0.0000 O   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
    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  2  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  1  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  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
 37 29  1  1  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  6  0  0  0
 22 39  1  0  0  0  0
  3 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1OC=C2[C@@H](C[C@@H]3N(CCC4=C3NC3=CC=CC=C43)C2=O)[C@H]1C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N2O9/c1-3-14-17-10-20-22-16(15-6-4-5-7-19(15)29-22)8-9-30(20)26(35)18(17)12-36-27(14)39-28-25(37-13(2)32)24(34)23(33)21(11-31)38-28/h3-7,12,14,17,20-21,23-25,27-29,31,33-34H,1,8-11H2,2H3/t14-,17+,20+,21-,23-,24+,25-,27+,28+/m1/s1

> <INCHI_KEY>
TXCIKXPZPJSBMS-PQZOUNHZSA-N

> <FORMULA>
C28H32N2O9

> <MOLECULAR_WEIGHT>
540.569

> <EXACT_MASS>
540.210780618

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.559392892051996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_LOGP>
0.41600461866666816

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.996011047191292

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.694475962311724

> <JCHEM_PKA_STRONGEST_BASIC>
0.048948129744745716

> <JCHEM_POLAR_SURFACE_AREA>
150.78000000000003

> <JCHEM_REFRACTIVITY>
136.0024

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  C   UNK     0       0.249  -1.748   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.264  -2.035   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.757  -0.294   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.762  -7.869   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.777 -11.369   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   39  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   39                                                  
CONECT    4    3    5   20                                                  
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   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   39                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   28   31                                                  
CONECT   37   29   25   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   22    3                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₂N₂O₉

Average Mass

540.5690 Da

Monoisotopic Mass

540.21078 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(1S,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1OC=C2[C@@H](C[C@@H]3N(CCC4=C3NC3=CC=CC=C43)C2=O)[C@H]1C=C

InChI Identifier

InChI=1S/C28H32N2O9/c1-3-14-17-10-20-22-16(15-6-4-5-7-19(15)29-22)8-9-30(20)26(35)18(17)12-36-27(14)39-28-25(37-13(2)32)24(34)23(33)21(11-31)38-28/h3-7,12,14,17,20-21,23-25,27-29,31,33-34H,1,8-11H2,2H3/t14-,17+,20+,21-,23-,24+,25-,27+,28+/m1/s1

InChI Key

TXCIKXPZPJSBMS-PQZOUNHZSA-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
Mostuea brunonis	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
3-alkylindole
Indole
Delta-lactam
Piperidinone
Monosaccharide
Oxane
Piperidine
Benzenoid
Pyrrole
Vinylogous ester
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Lactam
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen 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	0.42	ChemAxon
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	0.049	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136 m³·mol⁻¹	ChemAxon
Polarizability	56.56 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

9015474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10840175

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate (NP0330578)

MOL for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D MOL for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D SDF for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D-SDF for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

PDB for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D PDB for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

SMILES for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

INCHI for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

Structure for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D Structure for NP0330578 ((2s,3r,4s,5s,6r)-2-{[(1s,18s,19r,20s)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-18-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)