NP-MRD: Showing NP-Card for (2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate (NP0142467)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-01 21:01:08 UTC

Updated at

2022-09-01 21:01:09 UTC

NP-MRD ID

NP0142467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate

Description

Nigroside II 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. (2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate is found in Verbascum nigrum. Based on a literature review very few articles have been published on Nigroside II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012223012D          

 44 48  0  0  1  0            999 V2000
   -1.8342   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -5.1170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -5.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049   -6.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8118   -6.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -5.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089   -5.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  1  0  0  0
  6 28  1  0  0  0  0
 11 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
  2 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
    2.6052   -3.8674   -2.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396   -4.2582   -0.7683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1011   -3.4510   -0.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -2.1441   -0.0644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4083   -1.4539    0.4006 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0586   -0.3617   -0.3925 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1978    0.8479    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    1.3441    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1255    2.5641    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    2.2383    2.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898    0.5454    0.2251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0230    1.4764   -0.4529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2754    1.0067   -0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3165    1.6813   -0.1078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0897    0.9006    0.7176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7499   -0.1205    0.0971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1061   -1.4656    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1710   -1.6258    1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9350    0.0355   -1.3744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0713   -0.7106   -1.7544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2984    1.4924   -1.6405 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5647    1.6085   -2.9953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1076    2.3264   -1.2318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5034    3.6318   -0.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135    2.0204   -1.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256    1.0559   -2.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -0.0922   -2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -0.3561   -0.7593 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5836   -2.0845    1.0051 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7456   -1.5315    0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -0.3897    0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7304    0.1150    1.9670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4885    0.2527    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741    1.3342    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1482    2.0489    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8996    1.6699   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0283    2.3901   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4251    3.5185   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6647    3.9040    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564    3.1933    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -3.5131    1.4519 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7547   -3.5892    2.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862   -4.2746    0.2142 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7075   -5.5608    0.5131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961   -3.0859   -2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487   -3.6042   -2.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851   -4.7814   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -5.2883   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -1.6280   -0.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088   -0.2234   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1646    1.2774    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333    3.3926    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628    2.9568    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792    2.8751    2.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.1079    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    2.3639    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9580    2.5484    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7807   -0.1765    0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5996   -2.2829   -0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278   -1.3634    0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886   -1.6724    2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780   -0.2991   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6644   -0.8572   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1758    1.7303   -1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2678    2.3004   -3.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    2.4424   -2.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7851    3.9738   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    1.2504   -3.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4180   -0.8625   -2.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254   -1.4430   -0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -1.4826    1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0041   -0.1588   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243    1.7141    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6496    0.8008   -1.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5817    2.0411   -1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3030    4.0687   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9838    4.8052    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9990    3.5461    2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8431   -3.9351    1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -4.0224    3.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030   -3.6530   -0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2280   -5.5114    1.3584 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  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 28  1  0
 28 27  1  0
 27 26  2  0
 26 25  1  0
 25 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  4 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 29 41  1  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43  2  1  0
 28  6  1  0
 23 14  1  0
 40 35  1  0
 12 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  6
  4 49  1  6
  6 50  1  6
  7 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 11 55  1  1
 28 70  1  1
 27 69  1  0
 26 68  1  0
 12 56  1  1
 14 57  1  1
 16 58  1  1
 17 59  1  0
 17 60  1  0
 18 61  1  0
 19 62  1  6
 20 63  1  0
 21 64  1  1
 22 65  1  0
 23 66  1  6
 24 67  1  0
 29 71  1  1
 33 72  1  0
 34 73  1  0
 36 74  1  0
 37 75  1  0
 38 76  1  0
 39 77  1  0
 40 78  1  0
 41 79  1  1
 42 80  1  0
 43 81  1  6
 44 82  1  0
M  END


  Mrv1652309012223012D          

 44 48  0  0  1  0            999 V2000
   -1.8342   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710   -5.1170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -5.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049   -6.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8118   -6.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -5.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089   -5.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  1  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  1  0  0  0
  6 28  1  0  0  0  0
 11 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
  2 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0142467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2C=C(CO)[C@@H]3[C@H]2C=CO[C@H]3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O14/c1-14-22(34)25(37)27(43-20(33)8-7-15-5-3-2-4-6-15)30(40-14)41-18-11-16(12-31)21-17(18)9-10-39-28(21)44-29-26(38)24(36)23(35)19(13-32)42-29/h2-11,14,17-19,21-32,34-38H,12-13H2,1H3/b8-7+/t14-,17-,18+,19+,21+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1

> <INCHI_KEY>
CZZDQOSBWQATCP-JXXSAGFBSA-N

> <FORMULA>
C30H38O14

> <MOLECULAR_WEIGHT>
622.62

> <EXACT_MASS>
622.226155904

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
62.64305831928388

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R,6S)-2-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.8719048633333342

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.716562751504874

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.094641586784908

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7415130639193954

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
149.61409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R,6S)-2-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.424  -2.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925   7.167   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.253  -9.552   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.760 -10.192   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.267 -10.512   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.742 -11.977   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.249 -12.297   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.279 -11.153   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.803  -9.688   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.297  -9.368   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.315  -7.583   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.376  -5.294   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    6   11                                                  
CONECT   29    4   30   41                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   29   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    2   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₁₄

Average Mass

622.6200 Da

Monoisotopic Mass

622.22616 Da

IUPAC Name

(2R,3R,4R,5R,6S)-2-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2E)-3-phenylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2C=C(CO)[C@@H]3[C@H]2C=CO[C@H]3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H38O14/c1-14-22(34)25(37)27(43-20(33)8-7-15-5-3-2-4-6-15)30(40-14)41-18-11-16(12-31)21-17(18)9-10-39-28(21)44-29-26(38)24(36)23(35)19(13-32)42-29/h2-11,14,17-19,21-32,34-38H,12-13H2,1H3/b8-7+/t14-,17-,18+,19+,21+,22-,23+,24-,25+,26+,27+,28-,29-,30-/m0/s1

InChI Key

CZZDQOSBWQATCP-JXXSAGFBSA-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
Verbascum nigrum	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
Cinnamic acid or derivatives
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Aromatic monoterpenoid
Monoterpenoid
Bicyclic monoterpenoid
Styrene
Fatty acid ester
Benzenoid
Oxane
Monosaccharide
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.2	ALOGPS
logP	-0.87	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	149.61 m³·mol⁻¹	ChemAxon
Polarizability	62.64 Å³	ChemAxon
Number of Rings	5	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

10211952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21591415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate (NP0142467)

MOL for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0142467 ((2r,3r,4r,5r,6s)-2-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl (2e)-3-phenylprop-2-enoate)