NP-MRD: Showing NP-Card for (1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate (NP0328169)

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Record Information

Version

2.0

Created at

2022-09-12 11:23:59 UTC

Updated at

2022-09-12 11:23:59 UTC

NP-MRD ID

NP0328169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate

Description

Ipomoeassin C belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate is found in Ipomoea squamosa. Based on a literature review very few articles have been published on ipomoeassin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213242D          

 58 61  0  0  1  0            999 V2000
    4.0792    4.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733    4.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4640    4.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2581    4.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606    3.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8513    2.8796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    3.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    2.4324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8539    1.8565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6480    2.0801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.0569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0624    0.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0378   -0.3185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6285   -0.8944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4252   -1.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -1.9176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4277   -2.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0184   -3.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8150   -4.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462   -1.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -1.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.8608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2731   -1.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142   -0.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -0.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0892    0.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833    0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867    1.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959    2.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8808    1.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    1.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    1.4092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8564    0.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690    2.2087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8783    2.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    3.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8758    3.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909    4.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    4.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    5.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095    5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    5.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221    6.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    6.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070    6.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4227   -0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6260    0.1288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4201    0.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0353    0.7047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2387    1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0328    1.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2362    2.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6235    1.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2412    0.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1018    1.2942    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  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  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 11 36  1  6  0  0  0
 35 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
 14 49  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
 52 57  1  0  0  0  0
 13 57  1  0  0  0  0
 57 58  1  6  0  0  0
M  END

     RDKit          3D

116119  0  0  0  0  0  0  0  0999 V2000
    5.4503   -2.3635   -4.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5774   -1.3220   -5.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6549   -0.7264   -4.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012    0.3174   -5.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4506   -1.0550   -3.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.9227   -2.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794   -0.4314   -2.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976   -0.7656   -1.0640 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9123   -1.4118   -0.9270 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9524   -2.7052   -1.4969 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.5865    0.5520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3197   -2.4271    0.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -2.2753    0.0068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2132   -1.0710    0.5067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3158   -0.9041   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959    0.3703   -0.7966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7599    0.7493   -2.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1889    0.1296   -3.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -1.3496   -3.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9861    0.7234   -0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    2.2036   -0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8354    2.5852    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6782    4.1037    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2365    4.4489    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558    5.4202   -0.0765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1966    5.3631   -1.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1705    5.3022   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928    6.2881   -0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    4.0634    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    4.1706   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9345    4.0512    1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297    5.0796    1.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016    2.9616    1.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5030    1.7075    1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603    0.7020    0.6314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5360   -0.3802    1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    0.4266   -0.1386 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5639    0.2595    0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375    1.1130    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5955    2.0532   -0.4119 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8864    0.9762    1.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9657    0.0037    2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1327   -0.2558    2.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0914   -1.3199    3.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1590   -1.6127    4.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798   -0.8382    4.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3862    0.2185    3.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798    0.4937    2.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166   -1.1375    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5192   -3.5129    1.7249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0210   -4.6884    2.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8919   -6.7932    3.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5536   -3.0252   -0.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0728   -1.9402   -3.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -1.0447   -6.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273    1.2350   -4.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147    0.6320   -6.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8051   -0.0918   -5.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -1.5643   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1435   -0.7848   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -3.2054   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6727   -2.0752    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -2.1571   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -0.1787    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157    1.0584    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599    0.6915   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9374    1.8642   -2.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2255    0.4327   -3.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8113    2.6261   -1.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8895    2.3063    0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6065    3.5457    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2245    4.9361    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    6.4549    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    4.7356   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    3.1921   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    3.9730    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122213242D          

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 13 57  1  0  0  0  0
 57 58  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0328169

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H]1CCCCC[C@H](O)C(=O)CCC(=O)OC[C@@H]2O[C@@H](O[C@H]3[C@H](O)[C@H](OC(C)=O)[C@H](C)O[C@@H]3O1)[C@H](O)[C@@H](OC(=O)C(\C)=C/C)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C42H58O16/c1-6-14-28-17-12-9-13-18-29(44)30(45)20-22-32(46)51-23-31-37(56-33(47)21-19-27-15-10-8-11-16-27)38(57-40(50)24(3)7-2)35(49)41(55-31)58-39-34(48)36(53-26(5)43)25(4)52-42(39)54-28/h7-8,10-11,15-16,19,21,25,28-29,31,34-39,41-42,44,48-49H,6,9,12-14,17-18,20,22-23H2,1-5H3/b21-19+,24-7-/t25-,28-,29-,31-,34+,35+,36+,37+,38+,39-,41-,42+/m0/s1

> <INCHI_KEY>
RTVXDHYKIASJTP-MUDHPVDRSA-N

> <FORMULA>
C42H58O16

> <MOLECULAR_WEIGHT>
818.91

> <EXACT_MASS>
818.372485788

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
84.81147815417337

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4R,5S,6S,8S,10S,16S,23S,24R,25R,26R)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
5.788106437666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.910909352733821

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.211753592443538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4943672998562727

> <JCHEM_POLAR_SURFACE_AREA>
219.87999999999994

> <JCHEM_REFRACTIVITY>
204.02439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4R,5S,6S,8S,10S,16S,23S,24R,25R,26R)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.614   8.600   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.097   9.018   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.199   7.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.682   8.360   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.820   6.450   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.923   5.375   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.337   6.033   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.958   4.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.061   3.465   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.543   3.883   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.681   1.973   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.450   1.460   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.404  -0.595   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.507  -1.670   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.127  -3.162   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.645  -3.579   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.265  -5.072   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.368  -6.147   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.988  -7.639   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.542  -2.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.060  -2.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.957  -1.847   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.475  -2.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.372  -1.189   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.890  -1.607   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.510  -3.099   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.213  -0.532   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.696  -0.949   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.166   0.961   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.649   1.378   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.028   2.871   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.926   3.946   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.511   3.288   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.613   2.213   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.096   2.631   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.199   1.555   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.475   4.123   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.373   5.198   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.752   6.690   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.235   7.108   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.650   7.765   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.029   9.258   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.927  10.333   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.444   9.916   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.342  10.991   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.721  12.483   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.204  12.900   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.306  11.825   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      11.989  -1.252   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      12.369   0.240   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      13.851   0.658   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.266   1.315   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      11.646   2.808   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      13.128   3.225   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.508   4.718   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      14.231   2.150   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       9.784   0.898   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       9.523   2.416   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   37                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   57                                                  
CONECT   14   13   15   49                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   11                                                       
CONECT   37   35    8   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   43                                                       
CONECT   49   14   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
CONECT   57   52   13   58                                                  
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₅₈O₁₆

Average Mass

818.9100 Da

Monoisotopic Mass

818.37249 Da

IUPAC Name

(1S,3S,4R,5S,6S,8S,10S,16S,23S,24R,25R,26R)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2Z)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC[C@H]1CCCCC[C@H](O)C(=O)CCC(=O)OC[C@@H]2O[C@@H](O[C@H]3[C@H](O)[C@H](OC(C)=O)[C@H](C)O[C@@H]3O1)[C@H](O)[C@@H](OC(=O)C(\C)=C/C)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C42H58O16/c1-6-14-28-17-12-9-13-18-29(44)30(45)20-22-32(46)51-23-31-37(56-33(47)21-19-27-15-10-8-11-16-27)38(57-40(50)24(3)7-2)35(49)41(55-31)58-39-34(48)36(53-26(5)43)25(4)52-42(39)54-28/h7-8,10-11,15-16,19,21,25,28-29,31,34-39,41-42,44,48-49H,6,9,12-14,17-18,20,22-23H2,1-5H3/b21-19+,24-7-/t25-,28-,29-,31-,34+,35+,36+,37+,38+,39-,41-,42+/m0/s1

InChI Key

RTVXDHYKIASJTP-MUDHPVDRSA-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
Ipomoea squamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Tetracarboxylic acid or derivatives
Macrolide
Cinnamic acid ester
Cinnamic acid or derivatives
Alkyl glycoside
Disaccharide
Styrene
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.79	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	219.88 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	204.02 m³·mol⁻¹	ChemAxon
Polarizability	84.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042623

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

102397822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate (NP0328169)

MOL for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

PDB for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

Structure for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0328169 ((1s,3s,4r,5s,6s,8s,10s,16s,23s,24r,25r,26r)-5-(acetyloxy)-4,16,26-trihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2z)-2-methylbut-2-enoate)