NP-MRD: Showing NP-Card for (2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid (NP0211937)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 10:25:19 UTC

Updated at

2022-09-05 10:25:20 UTC

NP-MRD ID

NP0211937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid

Description

Theopederin B belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring. (2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid is found in Theonella swinhoei. (2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid was first documented in 2005 (PMID: 15958059). Based on a literature review very few articles have been published on Theopederin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212252D          

 40 42  0  0  1  0            999 V2000
    0.6804   -5.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -3.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0980   -2.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -3.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5223    2.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5269   -2.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572   -3.3762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8697   -3.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -4.1515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3054   -4.7835    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  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 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  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 35 34  1  1  0  0  0
 12 35  1  0  0  0  0
 16 35  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END

     RDKit          3D

 87 89  0  0  0  0  0  0  0  0999 V2000
   -7.7998    1.5276    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4863    1.5380    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5261    0.7717    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    0.4774    0.5257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5480   -0.3581   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1456   -1.5400   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364   -0.2306    1.3938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8407    0.5139    2.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9640   -0.4707    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318    0.6977    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701   -1.5612    0.3963 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -2.6713    0.0188 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9009   -2.9935   -1.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -4.3337   -1.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5687   -4.6568   -0.6635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116   -3.5229   -0.5625 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6623   -3.6640    0.0796 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4289   -4.4816   -0.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7153   -5.7020   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540   -2.3192    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -2.2557   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115   -2.3551    1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3812   -1.1335    0.1362 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7957   -0.3039   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0965    1.0154   -1.1242 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137    1.7147   -2.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073    1.8334    0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767    2.2180    0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3540    3.0371   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    3.3554    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    2.9275    1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6338    4.1115   -0.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8914    4.3856    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381   -1.3288    0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736   -2.5602    0.3871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6616    1.5970   -0.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4197    2.6724   -0.3023 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3292    3.8336    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8828    2.3652   -0.6331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6415    3.6242   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4271    2.1009   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2805    0.9233    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3342    1.3896    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0576   -0.1250    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2862   -2.0695   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6221   -2.2518    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150   -1.3629    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6289   -1.1887    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5024    1.3773    2.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442    1.1843    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436   -3.6254    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -5.0224   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -4.4517   -2.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205   -3.0204   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822   -4.2365    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -6.2656    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -5.5896    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657   -6.2545   -0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423   -2.1959   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2186   -1.4945   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088   -3.2431   -0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3871   -3.2802    1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -2.3363    2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3972   -1.4383    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5368   -0.4430    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -0.1283   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578   -0.8357   -2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889    0.8398   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042    2.6269   -2.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578    2.8000   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633    1.3963    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191    1.3611    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671    2.8152    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5316    2.4947   -1.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8234    3.9833   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7405    4.0706   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9538    3.9577    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9257    5.5014    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -2.8861    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0193    3.0973   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    4.6709    0.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8041    3.6538    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    4.1821    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9087    1.7546   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0731    4.0871    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5217    3.3681   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0362    4.3342   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 39  1  0
 39 40  1  0
 39 37  1  0
 37 38  1  0
 37 36  1  0
  4  5  1  6
  5  6  1  0
 12 35  1  0
 35 34  1  0
 34 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 23 20  1  0
 20 21  1  0
 20 22  1  0
 20 17  1  0
 35 16  1  0
 36  4  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 17 55  1  1
 16 54  1  6
 14 52  1  0
 14 53  1  0
 12 51  1  1
 10 50  1  0
  7 48  1  1
  8 49  1  0
  3 43  1  0
  3 44  1  0
  1 41  1  0
  1 42  1  0
 39 84  1  6
 40 85  1  0
 40 86  1  0
 40 87  1  0
 37 80  1  6
 38 81  1  0
 38 82  1  0
 38 83  1  0
  6 45  1  0
  6 46  1  0
  6 47  1  0
 35 79  1  1
 23 65  1  1
 24 66  1  0
 24 67  1  0
 25 68  1  6
 26 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 33 76  1  0
 33 77  1  0
 33 78  1  0
 21 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
M  END


  Mrv1652309052212252D          

 40 42  0  0  1  0            999 V2000
    0.6804   -5.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -3.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0980   -2.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -3.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5223    2.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5269   -2.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572   -3.3762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8697   -3.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -4.1515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3054   -4.7835    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  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 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  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 35 34  1  1  0  0  0
 12 35  1  0  0  0  0
 16 35  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0211937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H]2OCO[C@H](N=C(O)[C@@H](O)[C@]3(CC(=C)[C@@H](C)[C@@H](C)O3)OC)[C@@H]2O[C@H](C[C@H](O)CCCC(=O)OC)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H47NO11/c1-15-13-28(36-8,40-17(3)16(15)2)23(32)25(33)29-26-22-21(37-14-38-26)24(35-7)27(4,5)19(39-22)12-18(30)10-9-11-20(31)34-6/h16-19,21-24,26,30,32H,1,9-14H2,2-8H3,(H,29,33)/t16-,17-,18-,19-,21+,22-,23-,24-,26+,28-/m1/s1

> <INCHI_KEY>
HNGPDWRIFRLACY-HRALQUFGSA-N

> <FORMULA>
C28H47NO11

> <MOLECULAR_WEIGHT>
573.68

> <EXACT_MASS>
573.314911337

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.52927260442996

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(4S,4aR,6R,8S,8aR)-6-[(2R)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid

> <JCHEM_LOGP>
2.4159949536666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.502052166796481

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8658060806142793

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5467594728338052

> <JCHEM_POLAR_SURFACE_AREA>
154.73

> <JCHEM_REFRACTIVITY>
141.55849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(4S,4aR,6R,8S,8aR)-6-[(2R)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic 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       1.270  -9.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.797  -8.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.807  -6.837   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.183  -5.123   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.173  -6.302   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.344   5.030   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.324   5.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.708   4.487   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.850  -5.123   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.840  -6.302   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.357  -6.035   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.313  -7.749   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.303  -8.929   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   36                                             
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   23   35                                                       
CONECT   35   34   12   16                                                  
CONECT   36    4   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇NO₁₁

Average Mass

573.6800 Da

Monoisotopic Mass

573.31491 Da

IUPAC Name

(2R)-N-[(4S,4aR,6R,8S,8aR)-6-[(2R)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid

Traditional Name

(2R)-N-[(4S,4aR,6R,8S,8aR)-6-[(2R)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H]2OCO[C@H](N=C(O)[C@@H](O)[C@]3(CC(=C)[C@@H](C)[C@@H](C)O3)OC)[C@@H]2O[C@H](C[C@H](O)CCCC(=O)OC)C1(C)C

InChI Identifier

InChI=1S/C28H47NO11/c1-15-13-28(36-8,40-17(3)16(15)2)23(32)25(33)29-26-22-21(37-14-38-26)24(35-7)27(4,5)19(39-22)12-18(30)10-9-11-20(31)34-6/h16-19,21-24,26,30,32H,1,9-14H2,2-8H3,(H,29,33)/t16-,17-,18-,19-,21+,22-,23-,24-,26+,28-/m1/s1

InChI Key

HNGPDWRIFRLACY-HRALQUFGSA-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
Theonella swinhoei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranodioxins

Sub Class

Not Available

Direct Parent

Pyranodioxins

Alternative Parents

Substituents

Pyranodioxin
Ketal
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Meta-dioxane
Methyl ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.42	ChemAxon
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	154.73 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	141.56 m³·mol⁻¹	ChemAxon
Polarizability	61.53 Å³	ChemAxon
Number of Rings	3	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

134820451

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee KH, Nishimura S, Matsunaga S, Fusetani N, Horinouchi S, Yoshida M: Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products. Cancer Sci. 2005 Jun;96(6):357-64. doi: 10.1111/j.1349-7006.2005.00055.x. [PubMed:15958059 ]
LOTUS database [Link]

Showing NP-Card for (2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid (NP0211937)

MOL for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

3D MOL for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

3D SDF for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

3D-SDF for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

PDB for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

3D PDB for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

SMILES for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

INCHI for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

Structure for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)

3D Structure for NP0211937 ((2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2r)-2-hydroxy-6-methoxy-6-oxohexyl]-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid)