NP-MRD: Showing NP-Card for methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0243665)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 04:15:58 UTC

Updated at

2022-09-07 04:15:58 UTC

NP-MRD ID

NP0243665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

MEGxp0_001174 belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Duranta erecta. Based on a literature review very few articles have been published on MEGxp0_001174.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206152D          

 43 46  0  0  1  0            999 V2000
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6551   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4801   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6551    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    0.0000 O   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  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  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
 31 40  1  0  0  0  0
 25 41  1  0  0  0  0
 21 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
M  END

     RDKit          3D

 79 82  0  0  0  0  0  0  0  0999 V2000
   -3.5682   -1.1821   -6.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161   -0.5744   -5.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599   -1.1729   -4.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -2.2830   -4.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974   -0.5548   -2.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    0.5901   -2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315    1.1996   -1.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    0.3236   -0.2051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0852   -0.1183    0.1015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829    0.3470    1.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6765   -0.6485    2.2661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9043   -1.2337    2.3203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0640   -2.3919    1.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966   -2.0120    0.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0780   -0.3094    2.2896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9799   -0.5384    3.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5394    1.1064    2.4156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5174    2.0554    2.5760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6463    1.3231    1.2283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2139    2.6602    1.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8289   -0.7822   -0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6723   -1.2844   -1.7877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0690   -2.6378   -1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -1.1670   -2.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236   -0.2609   -1.1453 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7169   -0.4367   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    0.4710   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044    1.6255   -0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744    0.1426   -0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438    1.0102   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3846    0.7076    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8096   -0.5371    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1233   -0.7345    1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0278    0.3143    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3321    0.1531    1.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8780   -1.0550    2.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6048    1.5458    0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4755    2.6232    0.9382 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0441    3.8992    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3149    1.7217    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711   -0.4315    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3841    0.7759    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0449   -1.5058    0.8542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6293   -1.4667   -6.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947   -2.0592   -6.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150   -0.4606   -7.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768    1.1077   -3.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506    0.9463    0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6450    0.9772    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528   -1.7522    3.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0706   -2.8482    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3448   -3.2080    1.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245   -2.5091   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6419   -0.3959    1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8349   -0.1274    3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8630    1.1006    3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0638    2.1107    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770    1.2237    0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3033    2.7517    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186   -1.6390    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302   -2.8831   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -0.7240   -3.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824   -2.1711   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.8053   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2560   -0.8809    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8123    2.0250   -0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1153   -1.3477    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4629   -1.7022    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8083   -0.9295    2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1286   -1.6407    2.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1562   -1.6410    1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1938    4.2163    1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8433    4.6371    0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7614    3.9017   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0180    2.7238    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5872    1.7334    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9173    0.6193    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    0.8539    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984   -2.0904    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 41  1  0
 41 42  1  0
 41 43  1  1
 41 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  1
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 34 37  1  0
 37 38  1  0
 38 39  1  0
 37 40  2  0
 22  5  1  0
 40 31  1  0
 19 10  1  0
 22 21  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  6 47  1  0
  8 48  1  1
 10 49  1  1
 12 50  1  1
 13 51  1  0
 13 52  1  0
 14 53  1  0
 15 54  1  6
 16 55  1  0
 17 56  1  1
 18 57  1  0
 19 58  1  6
 20 59  1  0
 21 60  1  1
 42 76  1  0
 42 77  1  0
 42 78  1  0
 43 79  1  0
 25 64  1  6
 24 62  1  0
 24 63  1  0
 23 61  1  0
 29 65  1  0
 30 66  1  0
 32 67  1  0
 33 68  1  0
 36 69  1  0
 36 70  1  0
 36 71  1  0
 39 72  1  0
 39 73  1  0
 39 74  1  0
 40 75  1  0
M  END


  Mrv1652309072206152D          

 43 46  0  0  1  0            999 V2000
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6551   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4801   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6551    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    0.0000 O   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  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  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
 31 40  1  0  0  0  0
 25 41  1  0  0  0  0
 21 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0243665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@](C)(O)[C@H](C[C@]12O)OC(=O)\C=C\C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O15/c1-27(35)18(42-19(30)8-6-13-5-7-15(37-2)16(9-13)38-3)10-28(36)14(24(34)39-4)12-40-26(23(27)28)43-25-22(33)21(32)20(31)17(11-29)41-25/h5-9,12,17-18,20-23,25-26,29,31-33,35-36H,10-11H2,1-4H3/b8-6+/t17-,18+,20-,21+,22-,23-,25+,26+,27+,28+/m1/s1

> <INCHI_KEY>
FQNAUMYJWYEZSE-WZSBKURHSA-N

> <FORMULA>
C28H36O15

> <MOLECULAR_WEIGHT>
612.581

> <EXACT_MASS>
612.205420459

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
60.4152828362527

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aR,6S,7R,7aS)-6-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
-1.3081179640000011

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.886652622782577

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.153334749669705

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847602351753

> <JCHEM_POLAR_SURFACE_AREA>
220.12999999999997

> <JCHEM_REFRACTIVITY>
142.46629999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aR,6S,7R,7aS)-6-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.789  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.877  -1.897   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.203  -1.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.743  -1.897   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.513  -3.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.053  -3.231   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.823  -1.897   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.363  -1.897   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -9.133  -0.564   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.053  -0.564   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.823   0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.053   2.104   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.513  -0.564   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.627  -1.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   41                                                  
CONECT   22   21    5   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   41                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   31                                                       
CONECT   41   25   21   42   43                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₁₅

Average Mass

612.5810 Da

Monoisotopic Mass

612.20542 Da

IUPAC Name

methyl (1S,4aR,6S,7R,7aS)-6-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@](C)(O)[C@H](C[C@]12O)OC(=O)\C=C\C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C28H36O15/c1-27(35)18(42-19(30)8-6-13-5-7-15(37-2)16(9-13)38-3)10-28(36)14(24(34)39-4)12-40-26(23(27)28)43-25-22(33)21(32)20(31)17(11-29)41-25/h5-9,12,17-18,20-23,25-26,29,31-33,35-36H,10-11H2,1-4H3/b8-6+/t17-,18+,20-,21+,22-,23-,25+,26+,27+,28+/m1/s1

InChI Key

FQNAUMYJWYEZSE-WZSBKURHSA-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
Duranta erecta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Cinnamic acid ester
Hexose monosaccharide
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Bicyclic monoterpenoid
Aromatic monoterpenoid
Monoterpenoid
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenol ether
Styrene
Phenoxy compound
Methoxybenzene
Fatty acid ester
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Ether
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.3	ChemAxon
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	220.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142.47 m³·mol⁻¹	ChemAxon
Polarizability	60.42 Å³	ChemAxon
Number of Rings	4	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

23551052

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23844064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0243665)

MOL for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0243665 (methyl (1s,4ar,6s,7r,7as)-6-{[(2e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy}-4a,7-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)