NP-MRD: Showing NP-Card for Holantosine A (NP0067697)

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Record Information

Version

2.0

Created at

2022-04-28 12:32:15 UTC

Updated at

2022-04-28 12:32:16 UTC

NP-MRD ID

NP0067697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Holantosine A

Description

(1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icosane-2,6-diol belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Holantosine A is found in Holarrhena antidysenterica . Based on a literature review very few articles have been published on (1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icosane-2,6-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214322D          

 35 40  0  0  1  0            999 V2000
    3.6048   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.3119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7791    1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602    1.1719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4637    0.5131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7860   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    0.6137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3226    1.3732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8191    2.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6380    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037    1.4738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0072    0.8150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3294    0.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729    1.0836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7584    1.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    2.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694    0.4248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7963   -0.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    0.0325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287    2.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202    0.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -0.5482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0613   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836   -1.4082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8870   -2.0671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0682   -1.9665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7459   -1.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -2.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093   -2.8265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  1  0  0  0
 18 21  1  6  0  0  0
 18 22  1  1  0  0  0
 11 23  1  1  0  0  0
  5 24  1  6  0  0  0
  2 25  1  1  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 29 33  1  6  0  0  0
 28 34  1  1  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 82 87  0  0  0  0  0  0  0  0999 V2000
    7.3649    1.9387    2.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6785    0.9526    1.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0968    1.4716    0.1738 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6036    1.2956    0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047   -0.1372   -0.1204 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8438   -0.2004   -0.4160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500   -0.9732    0.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2220   -0.0531    1.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2533   -0.9185    1.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -1.4894    0.9755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5181   -2.5499    1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050   -2.0696   -0.2203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3285   -1.3551   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007   -1.2977   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940   -1.1883   -0.5015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -0.4809    0.4443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4142    0.3072    1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1394    1.3904    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378    0.7944   -0.2567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3991    1.7085   -1.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7614    1.5362   -1.7036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3165    1.7604   -0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2475    3.2094   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6429    1.3437   -0.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5009    0.8792    0.4349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0722   -0.4941    0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -1.4341    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -0.5933   -0.6740 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2729   -0.7032   -2.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710   -2.1606   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8790   -0.6851   -1.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -0.6258   -1.0474 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8855   -1.3149   -2.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487    0.8388   -1.0979 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9368    1.4394   -2.2096 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6589    2.7381    2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347    2.4138    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8487    1.5634    2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302    2.5544    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008    1.5922    1.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697    1.9978   -0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864   -0.7245    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8976   -1.3432    1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    0.7244    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.4868    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -0.4511    2.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -1.7743    2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -2.9563    2.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -3.4509    1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435   -2.1739    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985   -3.1095   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239   -1.9940   -2.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -0.3770   -1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0132   -0.3547   -2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -2.1736   -2.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7308   -2.2728   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5501    2.1120    1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0663    1.7695    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9278   -0.6165   -0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4071   -0.7770    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3472   -2.2545   -0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -1.8947    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4473   -1.6443   -2.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929   -2.2923   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -3.1041    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -1.1215   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8575   -0.8182   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0436    0.9229   -2.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
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 17 18  1  0
 19 18  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 22 25  1  0
 25 26  1  0
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 28 29  1  6
 12 30  1  0
  5 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34  3  1  0
 30  7  1  0
 16 10  1  0
 25 19  1  0
 28 15  1  0
 28 19  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  6
  4 40  1  0
  4 41  1  0
  5 42  1  1
  7 43  1  1
  8 44  1  0
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  9 46  1  0
  9 47  1  0
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 11 50  1  0
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 16 57  1  6
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 18 60  1  0
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 23 64  1  0
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 25 68  1  1
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 26 70  1  0
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 32 76  1  1
 33 77  1  0
 33 78  1  0
 33 79  1  0
 34 80  1  6
 35 81  1  0
 35 82  1  0
M  END


  Mrv1652304282214322D          

 35 40  0  0  1  0            999 V2000
    3.6048   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.3119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7791    1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602    1.1719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4637    0.5131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7860   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    0.6137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3226    1.3732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8191    2.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6380    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037    1.4738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0072    0.8150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1483   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9952    0.0325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9671   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202    0.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -0.5482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.3836   -1.4082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8870   -2.0671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0682   -1.9665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7459   -1.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -2.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093   -2.8265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247   -2.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  1  0  0  0
 18 21  1  6  0  0  0
 18 22  1  1  0  0  0
 11 23  1  1  0  0  0
  5 24  1  6  0  0  0
  2 25  1  1  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 29 33  1  6  0  0  0
 28 34  1  1  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H](O[C@H]2CC[C@]3(C)[C@@H](CC[C@H]4[C@H]3CC[C@]35CO[C@@](C)(O)[C@H]3CC[C@]45O)C2)O[C@@H](C)[C@H]1N

> <INCHI_IDENTIFIER>
InChI=1S/C28H47NO6/c1-16-24(29)21(32-4)14-23(34-16)35-18-7-10-25(2)17(13-18)5-6-20-19(25)8-11-27-15-33-26(3,30)22(27)9-12-28(20,27)31/h16-24,30-31H,5-15,29H2,1-4H3/t16-,17-,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-,28-/m0/s1

> <INCHI_KEY>
XPLAXRSHXHPUNS-FQLCGZSCSA-N

> <FORMULA>
C28H47NO6

> <MOLECULAR_WEIGHT>
493.685

> <EXACT_MASS>
493.340338237

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.22558017415332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icosane-2,6-diol

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.6448936303333332

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.097250925899164

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.047333564008957

> <JCHEM_PKA_STRONGEST_BASIC>
9.132847583106575

> <JCHEM_POLAR_SURFACE_AREA>
103.4

> <JCHEM_REFRACTIVITY>
131.1062

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icosane-2,6-diol

> <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       6.729  -0.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.656   0.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.054   2.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.526   2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.599   0.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.200  -0.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.070   1.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.469   2.563   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.396   3.793   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   3.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.940   2.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.013   1.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.615   0.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.143  -0.084   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.443   2.023   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.416   3.563   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.057   4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.370   0.793   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.486  -0.469   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.014  -0.018   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.698   1.572   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.724   0.061   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.734   4.071   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.672  -0.272   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.184   0.394   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.786  -1.023   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.314  -1.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.916  -2.629   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.989  -3.859   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.461  -3.671   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.859  -2.253   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.534  -4.901   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      11.591  -5.276   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      13.445  -2.817   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.046  -4.234   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   24                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   23                                             
CONECT   12   11   13   15   20                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   21   22                                             
CONECT   19   18   20                                                       
CONECT   20   19   12                                                       
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23   11                                                            
CONECT   24    5                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇NO₆

Average Mass

493.6850 Da

Monoisotopic Mass

493.34034 Da

IUPAC Name

(1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icosane-2,6-diol

Traditional Name

(1S,2S,5S,6R,9R,12R,13R,16S,18S)-16-{[(2S,4R,5R,6S)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-6,13-dimethyl-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icosane-2,6-diol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H](O[C@H]2CC[C@]3(C)[C@@H](CC[C@H]4[C@H]3CC[C@]35CO[C@@](C)(O)[C@H]3CC[C@]45O)C2)O[C@@H](C)[C@H]1N

InChI Identifier

InChI=1S/C28H47NO6/c1-16-24(29)21(32-4)14-23(34-16)35-18-7-10-25(2)17(13-18)5-6-20-19(25)8-11-27-15-33-26(3,30)22(27)9-12-28(20,27)31/h16-24,30-31H,5-15,29H2,1-4H3/t16-,17-,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-,28-/m0/s1

InChI Key

XPLAXRSHXHPUNS-FQLCGZSCSA-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
Holarrhena pubescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
20-hydroxysteroid
Aminoglycoside core
Hydroxysteroid
14-hydroxysteroid
Amino saccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.25	ALOGPS
logP	2.64	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.11 m³·mol⁻¹	ChemAxon
Polarizability	56.23 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162911608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Holantosine A (NP0067697)

MOL for NP0067697 (Holantosine A)

3D MOL for NP0067697 (Holantosine A)

3D SDF for NP0067697 (Holantosine A)

3D-SDF for NP0067697 (Holantosine A)

PDB for NP0067697 (Holantosine A)

3D PDB for NP0067697 (Holantosine A)

SMILES for NP0067697 (Holantosine A)

INCHI for NP0067697 (Holantosine A)

Structure for NP0067697 (Holantosine A)

3D Structure for NP0067697 (Holantosine A)