NP-MRD: Showing NP-Card for 5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid (NP0235619)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 18:19:00 UTC

Updated at

2022-09-06 18:19:00 UTC

NP-MRD ID

NP0235619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid

Description

5-{[3-(Hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid 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. 5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid is found in Scorzonera pseudodivaricata. 5-{[3-(Hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500252D          

 41 43  0  0  0  0            999 V2000
   -4.0954   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    2.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -2.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 22 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 20 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END

     RDKit          3D

 77 79  0  0  0  0  0  0  0  0999 V2000
   -3.5345    3.1309   -3.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9869    2.9711   -3.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968    1.9388   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228    2.3802   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336    1.3876    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8992    0.0585   -0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3559   -0.2687   -1.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -0.9870    0.6044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091   -2.2429    0.4061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3694   -2.4546    1.4243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4485   -1.4216    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -1.5953    1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352   -0.4608    0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855   -0.5971    0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9383    0.6132    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4454    0.6597   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453   -0.2304   -1.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254    1.7544   -1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6807    1.6082   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413    2.6232   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5117    2.4056   -2.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4093    3.3489   -2.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5084    4.5779   -1.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4272    5.5393   -2.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580    4.8159   -0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7448    3.8559   -0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -1.8589    0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.8721    0.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578   -2.9883    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -4.3379    1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187   -5.3058    1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -4.6019    1.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -2.7904    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -2.1751    2.6438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9155   -3.0627    3.0593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8768   -2.3015    3.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4931   -1.2645    3.3110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7102   -3.7652    2.0289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6285   -5.1603    2.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051   -3.4091    0.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5604   -3.3702   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    2.1479   -3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    3.7591   -4.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306    3.6470   -2.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6136    2.6490   -4.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3659    3.9189   -2.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1966    1.8596   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    0.9527   -2.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329    2.3818   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5990    3.3936   -0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5065    1.3150    0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8509    1.8036    0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0391   -2.3400   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9803   -3.4689    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.4895    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753    0.6143    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317    1.5230    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    2.7599   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4255    1.6232   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9941    0.5674   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4723    1.8306    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4413    1.4576   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1052    3.1931   -3.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0352    5.3063   -3.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7301    5.7796   -0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074    4.1157    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615   -2.6382    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606   -4.9867    1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -3.6892    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4017   -3.8026    3.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609   -1.9130    4.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566   -3.0015    4.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2978   -0.4075    3.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8048   -3.5492    2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4537   -5.5757    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -4.2908    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0884   -2.5724    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 40  1  0
 40 41  1  0
 40 38  1  0
 38 39  1  0
 38 35  1  0
 35 36  1  0
 36 37  1  0
 35 34  1  0
 34 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 14 27  2  0
 27 28  1  0
 27 29  1  0
 29 33  2  0
 29 30  1  0
 30 32  1  0
 30 31  2  0
 10  9  1  0
 33 12  1  0
 26 20  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  2 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  0
  4 50  1  0
  5 51  1  0
  5 52  1  0
  9 53  1  6
 40 76  1  6
 41 77  1  0
 38 74  1  1
 39 75  1  0
 35 70  1  1
 36 71  1  0
 36 72  1  0
 37 73  1  0
 10 54  1  1
 13 55  1  0
 15 56  1  0
 15 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 21 62  1  0
 22 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 28 67  1  0
 33 69  1  0
 32 68  1  0
M  END


  Mrv1533004171500252D          

 41 43  0  0  0  0            999 V2000
   -4.0954   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -6.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    2.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    2.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -1.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -2.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 22 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 20 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)OC1C(O)C(O)C(CO)OC1OC1=CC(CC(=O)CCC2=CC=C(O)C=C2)=C(O)C(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O12/c1-2-3-4-5-23(33)41-27-26(36)25(35)22(15-30)40-29(27)39-20-13-17(24(34)21(14-20)28(37)38)12-19(32)11-8-16-6-9-18(31)10-7-16/h6-7,9-10,13-14,22,25-27,29-31,34-36H,2-5,8,11-12,15H2,1H3,(H,37,38)

> <INCHI_KEY>
HZXRJYJZHWLQDS-UHFFFAOYSA-N

> <FORMULA>
C29H36O12

> <MOLECULAR_WEIGHT>
576.595

> <EXACT_MASS>
576.220676599

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
59.82272339409889

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
3.8237142146666665

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.504966999889824

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.475196271973361

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810929895521605

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
143.1643

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -7.645 -10.574   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.105 -10.574   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.795  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.025  -7.906   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.485  -7.906   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.715  -6.573   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.715  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.825  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.595 -10.574   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.825 -11.907   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.135 -10.574   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.905 -11.907   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.905  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.445  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.215 -10.574   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.135  -7.906   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.595  -7.906   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.825  -6.573   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.595  -5.239   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.825  -3.905   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.595  -2.572   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.825  -1.238   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.715  -1.238   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.485  -2.572   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.485   0.096   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.025   0.096   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.795   1.429   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   1.429   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.105   2.763   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335   4.097   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.105   5.430   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.795   4.097   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.025   2.763   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.135  -2.572   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.905  -1.238   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.905  -3.905   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.135  -5.239   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.445  -3.905   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.215  -5.239   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.215  -2.572   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
CONECT   35   22   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37   20                                                       
CONECT   39   37   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
5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoate	Generator

Chemical Formula

C₂₉H₃₆O₁₂

Average Mass

576.5950 Da

Monoisotopic Mass

576.22068 Da

IUPAC Name

5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid

Traditional Name

5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)OC1C(O)C(O)C(CO)OC1OC1=CC(CC(=O)CCC2=CC=C(O)C=C2)=C(O)C(=C1)C(O)=O

InChI Identifier

InChI=1S/C29H36O12/c1-2-3-4-5-23(33)41-27-26(36)25(35)22(15-30)40-29(27)39-20-13-17(24(34)21(14-20)28(37)38)12-19(32)11-8-16-6-9-18(31)10-7-16/h6-7,9-10,13-14,22,25-27,29-31,34-36H,2-5,8,11-12,15H2,1H3,(H,37,38)

InChI Key

HZXRJYJZHWLQDS-UHFFFAOYSA-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
Scorzonera pseudodivaricata	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
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Salicylic acid or derivatives
Hydroxybenzoic acid
Salicylic acid
4-alkoxyphenol
Benzoic acid
Benzoic acid or derivatives
Benzoyl
Phenoxy compound
Phenol ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Benzenoid
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.4	ALOGPS
logP	3.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	143.16 m³·mol⁻¹	ChemAxon
Polarizability	59.82 Å³	ChemAxon
Number of Rings	3	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

73316178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid (NP0235619)

MOL for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

3D MOL for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

3D SDF for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

3D-SDF for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

PDB for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

3D PDB for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

SMILES for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

INCHI for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

Structure for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)

3D Structure for NP0235619 (5-{[3-(hexanoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxy-3-[4-(4-hydroxyphenyl)-2-oxobutyl]benzoic acid)