NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0154618)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 11:33:52 UTC

Updated at

2022-09-02 11:33:53 UTC

NP-MRD ID

NP0154618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Description

[(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate 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,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Campsis grandiflora. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213332D          

 41 43  0  0  1  0            999 V2000
    8.2802    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   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
    4.7079    2.0625    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   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
    2.5645   -1.6500    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
    1.7798   -0.2549    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    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0654    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    1.8336    0.0000 O   0  0  0  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
    3.9934    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 26 23  1  1  0  0  0
 10 26  1  0  0  0  0
 16 26  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

     RDKit          3D

 75 77  0  0  0  0  0  0  0  0999 V2000
    3.4035   -2.3026   -3.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6576   -1.0406   -3.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -1.1334   -3.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    0.1582   -3.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7178    1.4039   -2.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786    1.3931   -1.3981 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0757    0.5186   -1.3437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517    0.1789   -0.1018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3993   -0.8016   -0.3722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -0.5057    0.0479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0376   -1.4841    1.0120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3237   -2.7543    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -2.8695   -0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4017   -4.1982   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854   -5.2441   -0.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5919   -1.6355   -1.1701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8867   -1.2663   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327    0.1312    0.0478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7879    0.8928    0.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2037    1.4327    1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4735    2.2162    1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167    1.2390    2.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6456    0.6968   -0.9226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9935    1.9171   -0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1712    0.9685   -2.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730   -0.4773   -1.0907 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7114   -0.3549    0.6957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3566   -0.8333    1.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6601   -2.1394    2.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -2.7403    3.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -2.8584    1.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    0.8077    0.9210 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6002    0.3447    1.8448 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001    0.8572    3.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8151    0.3038    4.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    1.8157    3.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065    1.1870   -0.4125 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9940    2.3473   -0.4536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3063    2.3589   -0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284    3.6378   -0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7602    1.2535   -1.3091 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7497   -2.9787   -4.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889   -2.0837   -4.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023   -2.8489   -2.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9202    1.6037   -3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.1950   -2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534    2.4388   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0328    1.0064    0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576    0.4768    0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.6731    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180   -4.2686   -1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223   -1.8959   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -1.9434    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7406   -1.3413   -1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1308    0.0465    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2257    1.6070    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3061    3.1516    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8478    2.4063    2.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9515    2.0780   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0929    1.9981    0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5700    2.8090   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018    1.5241   -2.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -0.3569   -2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2265   -1.1179    0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.1746    4.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -3.7923    3.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814   -2.7671    4.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    1.6607    1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213    0.6231    3.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.7834    4.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6834    0.7633    5.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202    0.3493   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6640    4.3723   -1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9755    4.0370    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1174    3.4578   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 23 25  1  6
 23 26  1  0
  8 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 37  6  1  0
 26 10  1  0
 26 16  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  1
  8 48  1  1
 10 49  1  1
 12 50  1  0
 14 51  1  0
 16 52  1  6
 17 53  1  0
 17 54  1  0
 18 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 24 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  6
 27 64  1  6
 30 65  1  0
 30 66  1  0
 30 67  1  0
 32 68  1  1
 35 69  1  0
 35 70  1  0
 35 71  1  0
 37 72  1  6
 40 73  1  0
 40 74  1  0
 40 75  1  0
M  END


  Mrv1652309022213332D          

 41 43  0  0  1  0            999 V2000
    8.2802    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   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
    4.7079    2.0625    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   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
    2.5645   -1.6500    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
    1.7798   -0.2549    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    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0654    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    1.8336    0.0000 O   0  0  0  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
    3.9934    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 26 23  1  1  0  0  0
 10 26  1  0  0  0  0
 16 26  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0154618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C(C=O)[C@H]3C[C@H](OC(C)=O)[C@](C)(O)[C@@H]23)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O15/c1-11(28)34-10-18-21(37-13(3)30)22(38-14(4)31)23(39-15(5)32)25(40-18)41-24-20-17(16(8-27)9-35-24)7-19(26(20,6)33)36-12(2)29/h8-9,17-25,33H,7,10H2,1-6H3/t17-,18-,19+,20-,21-,22+,23-,24+,25+,26+/m1/s1

> <INCHI_KEY>
QTUVOXCKBFYKTE-YQWDYXRPSA-N

> <FORMULA>
C26H34O15

> <MOLECULAR_WEIGHT>
586.543

> <EXACT_MASS>
586.189770395

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.82145953942811

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
-1.0675826683333338

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.62924747507314

> <JCHEM_PKA_STRONGEST_BASIC>
-3.398367154403009

> <JCHEM_POLAR_SURFACE_AREA>
196.48999999999998

> <JCHEM_REFRACTIVITY>
128.70470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      15.456   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.123   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.123   2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.787  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.877   3.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.989   2.786   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.949   3.423   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.453   6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.454   9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.121   8.470   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.454  10.780   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.455   8.470   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.122   9.240   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.789   9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   10   16                                                  
CONECT   27    8   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32    6   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6S)-6-{[(1S,4as,6S,7R,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₅

Average Mass

586.5430 Da

Monoisotopic Mass

586.18977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C(C=O)[C@H]3C[C@H](OC(C)=O)[C@](C)(O)[C@@H]23)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C26H34O15/c1-11(28)34-10-18-21(37-13(3)30)22(38-14(4)31)23(39-15(5)32)25(40-18)41-24-20-17(16(8-27)9-35-24)7-19(26(20,6)33)36-12(2)29/h8-9,17-25,33H,7,10H2,1-6H3/t17-,18-,19+,20-,21-,22+,23-,24+,25+,26+/m1/s1

InChI Key

QTUVOXCKBFYKTE-YQWDYXRPSA-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
Campsis grandiflora	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
Pentacarboxylic acid or derivatives
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Cyclic alcohol
Vinylogous ester
Tertiary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aldehyde
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	0.74	ALOGPS
logP	-1.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	196.49 Å²	ChemAxon
Rotatable Bond Count	14	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

10218881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21594951

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,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0154618)

MOL for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D MOL for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D SDF for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

PDB for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D PDB for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

SMILES for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

INCHI for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

Structure for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D Structure for NP0154618 ([(2r,3r,4s,5r,6s)-6-{[(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-formyl-7-hydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)