NP-MRD: Showing NP-Card for Picrioside A (NP0063923)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 08:14:33 UTC

Updated at

2022-04-28 08:14:33 UTC

NP-MRD ID

NP0063923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Picrioside A

Description

(3AR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Picrioside A is found in Picris hieracioides and Picris hieracioides L.var.japonica Regel . Based on a literature review very few articles have been published on (3aR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210142D          

 49 54  0  0  1  0            999 V2000
    3.6753    6.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609    5.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    6.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497    6.8279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4145    7.5095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2372    7.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7983    6.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6122    7.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    6.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132    5.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    4.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    7.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8047    7.8887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1737    8.6266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7193    9.3151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0883   10.0530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9118   10.1023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3663    9.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9973    8.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1898    9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5589   10.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2808   10.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338   10.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8957    9.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    8.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309    8.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693    9.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016    8.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001    8.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339    6.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196    6.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    5.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    6.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4976    7.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    5.7837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3526    5.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    4.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5149    4.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    4.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    5.4529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5149    5.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    5.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4295    5.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1995    3.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1995    6.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985    3.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    3.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    4.9154    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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  1  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  1  0  0  0
  6 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  1  0  0  0
 28 29  2  0  0  0  0
  4 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
 35 33  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 35 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  2  0  0  0  0
 42 46  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  0  0  0  0
  2 49  1  0  0  0  0
M  END

     RDKit          3D

 91 96  0  0  0  0  0  0  0  0999 V2000
   -3.4235    2.9541   -1.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5642    1.6478   -0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    0.7966   -1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -0.4468   -1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    1.3068   -1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1314    0.5615   -2.3056 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1294    0.7368   -3.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695   -0.4501   -4.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2566   -1.2675   -5.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0443   -0.8911   -3.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576   -2.0565   -4.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3177   -2.8046   -5.2832 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -2.1177   -3.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676   -1.1069   -2.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2337   -0.9022   -1.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952   -0.9581   -0.5271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119   -0.7652    0.3160 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3173   -1.8926    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8656   -1.7464    2.2618 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3791   -1.5007    2.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9994   -2.5817    1.5775 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758   -0.7878    3.1719 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1708    0.0197    3.7627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2512    0.1558    2.4319 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0953   -0.5675    2.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901    0.4963    1.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0468    1.3950    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8800   -0.2708   -2.8087 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1738   -0.1383   -1.5268 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5407   -1.2848   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.8308    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691   -1.5497    1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    0.6002   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1259    1.4260    0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    0.8789   -1.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8110    1.0522   -0.4549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8862    2.0915   -0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2698    1.5607   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5423    1.2453    1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6138    1.9935    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8588    1.7890    1.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9030    0.3467    1.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1289   -0.0210    3.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9615    0.4913    3.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888   -1.1109    3.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702   -1.3805    2.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4291   -2.4369    2.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7967   -0.4885    1.3081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6400    0.2834    0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031    3.3592   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    3.6833   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3806   -0.5056   -2.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7845    0.9251   -4.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482    1.6019   -3.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410   -1.1562   -6.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -0.7927   -5.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471   -2.2976   -5.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660   -2.8687   -3.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0332   -1.6652   -2.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213    0.0779   -2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783   -0.6099   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7928   -2.7680    2.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6272   -0.5387    1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8036   -1.4408    3.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8320   -2.2158    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6613   -1.3017    4.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611    0.9358    3.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208    1.0706    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.0092    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8603    0.9818    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2175    2.3278    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1259    0.7475   -3.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111    0.1685   -0.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1819    1.1628    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    2.4748    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083    1.9210   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272    0.3095   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7191    2.8155    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8460    2.6999   -1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4050    0.5946   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9888    2.2974   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4004    3.0939    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6784    2.0532    2.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7026    1.6375    0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1435   -1.5909    4.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -2.4065    3.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7868   -2.2972    1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8621   -3.4549    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2061   -1.1055    0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -0.3944    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453    1.0065    1.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
 47 46  1  0
 46 45  2  0
 45 43  1  0
 43 44  2  0
 43 42  1  0
 42 39  2  0
 39 40  1  0
 40 41  1  0
 39 38  1  0
 38 37  1  0
 37 36  1  0
 36 49  1  0
 49 48  1  0
 36  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  3
 33 35  1  0
 28 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 48 46  1  0
 35  6  1  0
 26 17  1  0
 48 42  1  0
 11 10  1  0
 35 29  1  0
 47 86  1  0
 47 87  1  0
 47 88  1  0
 45 85  1  0
 40 82  1  0
 40 83  1  0
 41 84  1  0
 38 80  1  0
 38 81  1  0
 37 78  1  0
 37 79  1  0
 36 77  1  6
 49 90  1  0
 49 91  1  0
 48 89  1  6
  1 50  1  0
  1 51  1  0
  6 52  1  6
  7 53  1  0
  7 54  1  0
  9 55  1  0
  9 56  1  0
  9 57  1  0
 28 72  1  6
 29 73  1  1
 34 74  1  0
 34 75  1  0
 35 76  1  1
 15 59  1  0
 15 60  1  0
 17 61  1  6
 19 62  1  1
 20 63  1  0
 20 64  1  0
 21 65  1  0
 22 66  1  1
 23 67  1  0
 24 68  1  1
 25 69  1  0
 26 70  1  1
 27 71  1  0
 13 58  1  0
M  END


  Mrv1652304282210142D          

 49 54  0  0  1  0            999 V2000
    3.6753    6.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609    5.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    6.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497    6.8279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4145    7.5095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2372    7.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7983    6.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6122    7.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    6.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132    5.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5484    4.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    7.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8047    7.8887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1737    8.6266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7193    9.3151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0883   10.0530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9118   10.1023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3663    9.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9973    8.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1898    9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5589   10.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2808   10.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338   10.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8957    9.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    8.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309    8.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693    9.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1016    8.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001    8.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339    6.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196    6.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9210    5.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    6.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4976    7.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    5.7837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3526    5.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    4.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5149    4.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    4.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599    5.4529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5149    5.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    5.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4295    5.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1995    3.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1995    6.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985    3.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4868    3.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    4.9154    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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  1  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  1  0  0  0
  6 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  1  0  0  0
 28 29  2  0  0  0  0
  4 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
 35 33  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 35 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  2  0  0  0  0
 42 46  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  0  0  0  0
  2 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(CO)CC[C@H](C[C@@H]12)C(=C)C(=O)O[C@H]1CC(C)=C2[C@@H]([C@@H]3OC(=O)C(=C)[C@H]13)C(CO[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H42O13/c1-14-7-22(39)28-19(11-37)6-5-18(9-21(14)28)16(3)34(44)47-24-8-15(2)26-23(40)10-20(29(26)33-27(24)17(4)35(45)49-33)13-46-36-32(43)31(42)30(41)25(12-38)48-36/h7,10,18,21,24-25,27,29-33,36-38,41-43H,3-6,8-9,11-13H2,1-2H3/t18-,21+,24+,25+,27-,29+,30-,31+,32+,33-,36-/m1/s1

> <INCHI_KEY>
HCKRLHVPHIPBKX-XMJXEVTPSA-N

> <FORMULA>
C36H42O13

> <MOLECULAR_WEIGHT>
682.719

> <EXACT_MASS>
682.262541412

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
70.30074956268862

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.7696549820000007

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.811359478566562

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.131879138160684

> <JCHEM_PKA_STRONGEST_BASIC>
-2.757661475778284

> <JCHEM_POLAR_SURFACE_AREA>
206.35

> <JCHEM_REFRACTIVITY>
173.05730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.861  11.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.527  10.711   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.093  11.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.639  12.745   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.507  14.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.043  14.133   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.090  13.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.609  13.256   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.319  11.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.238  10.792   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.490   9.273   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.298  14.634   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.835  14.726   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.524  16.103   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.676  17.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.365  18.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.902  18.858   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.750  17.572   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.062  16.195   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.288  17.665   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      15.977  19.042   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.591  20.235   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.516  20.051   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.139  17.296   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.408  15.629   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.098  16.438   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.983  17.974   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.923  15.443   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.427  15.808   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.117  12.975   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.157  11.771   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.719  10.337   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.366  12.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.929  13.434   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.326  10.796   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.658   9.409   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.326   8.021   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.828   7.679   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.032   8.639   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.032  10.179   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.828  11.139   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.496  10.655   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.402   9.409   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.496   8.163   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.972   6.698   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -5.972  12.119   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -3.171   6.177   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -4.642   5.723   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.642   9.175   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3   49                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    6   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    5   29                                                  
CONECT   29   28                                                            
CONECT   30    4   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   47                                                  
CONECT   39   38   40   44                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   35                                                       
CONECT   42   40   43   46                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39   45                                                  
CONECT   45   44                                                            
CONECT   46   42                                                            
CONECT   47   38   48                                                       
CONECT   48   47                                                            
CONECT   49    2                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,9as,9BS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-[(3as,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoic acid	Generator

Chemical Formula

C₃₆H₄₂O₁₃

Average Mass

682.7190 Da

Monoisotopic Mass

682.26254 Da

IUPAC Name

(3aR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate

Traditional Name

(3aR,4S,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-9-({[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(CO)CC[C@H](C[C@@H]12)C(=C)C(=O)O[C@H]1CC(C)=C2[C@@H]([C@@H]3OC(=O)C(=C)[C@H]13)C(CO[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)=CC2=O

InChI Identifier

InChI=1S/C36H42O13/c1-14-7-22(39)28-19(11-37)6-5-18(9-21(14)28)16(3)34(44)47-24-8-15(2)26-23(40)10-20(29(26)33-27(24)17(4)35(45)49-33)13-46-36-32(43)31(42)30(41)25(12-38)48-36/h7,10,18,21,24-25,27,29-33,36-38,41-43H,3-6,8-9,11-13H2,1-2H3/t18-,21+,24+,25+,27-,29+,30-,31+,32+,33-,36-/m1/s1

InChI Key

HCKRLHVPHIPBKX-XMJXEVTPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Picris hieracioides	Plant	KNApSAcK
Picris hieracioides L.var.japonica Regel	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Sesquiterpenoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen 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	0.39	ALOGPS
logP	0.77	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	206.35 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	173.06 m³·mol⁻¹	ChemAxon
Polarizability	70.3 Å³	ChemAxon
Number of Rings	6	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

162992028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Picrioside A (NP0063923)

MOL for NP0063923 (Picrioside A)

3D MOL for NP0063923 (Picrioside A)

3D SDF for NP0063923 (Picrioside A)

3D-SDF for NP0063923 (Picrioside A)

PDB for NP0063923 (Picrioside A)

3D PDB for NP0063923 (Picrioside A)

SMILES for NP0063923 (Picrioside A)

INCHI for NP0063923 (Picrioside A)

Structure for NP0063923 (Picrioside A)

3D Structure for NP0063923 (Picrioside A)