NP-MRD: Showing NP-Card for [3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate (NP0307381)

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Record Information

Version

2.0

Created at

2022-09-11 00:28:29 UTC

Updated at

2022-09-11 00:28:29 UTC

NP-MRD ID

NP0307381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate

Description

[3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate 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. [3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate is found in Viburnum phlebotrichum. [3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522502D          

 31 32  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
    7.0969    2.2468    0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752    2.2685    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980    1.0007    1.1535 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3235    0.1362    1.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    1.2260    1.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.3102   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -1.0623    0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.6717   -1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8251   -2.0542   -1.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693   -2.6634   -3.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859   -1.9366   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.4568    0.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -2.3568   -1.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436   -2.2629   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -0.9205   -0.4159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5786   -1.0553    0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    0.1514    0.5600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4542    0.2404    0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6360    0.3946    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7721    0.4522   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0422    0.6052    0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1685    0.7044    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4218    0.8603    2.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0651    0.6512    2.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7966    0.4965    2.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    1.3652    0.0955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3926    1.7536    0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480    1.2709   -1.3426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8703    2.1160   -1.5979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6435   -0.1477   -1.7041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6093   -0.2766   -2.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5934    3.1636   -0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5331    1.3134   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5549    3.2149    1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0258    0.7890    2.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8235   -0.5268    2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8644   -0.4683    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    1.9537    2.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1885    0.9477   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427    0.1413   -0.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -1.6910    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299   -0.9960    0.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317   -1.8310   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7910   -3.0414   -3.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5143   -1.9027   -3.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617   -3.4944   -2.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -2.8866    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -2.7657   -1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -0.3693    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    0.2286    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6966    0.3753   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9202    0.6478   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5456    0.9352    3.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1642    0.7293    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9321    0.4561    2.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461    2.2173    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    1.2991    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783    1.6141   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682    3.0560   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.6472   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    0.1228   -3.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  3  1  0
  3  4  1  0
  3  5  1  1
  3  2  1  0
  2  1  2  3
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 17 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 15  1  0
 25 19  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
  8 43  1  0
  7 41  1  0
  7 42  1  0
  6 39  1  0
  6 40  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  2 34  1  0
  1 32  1  0
  1 33  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 17 50  1  1
 20 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  6
 27 57  1  0
 28 58  1  6
 29 59  1  0
 30 60  1  6
 31 61  1  0
M  END


  Mrv1533004171522502D          

 31 32  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=CCCC(C)(O)C=C)C(=O)OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O9/c1-4-22(3,28)11-5-6-13(2)20(27)29-12-16-17(24)18(25)19(26)21(31-16)30-15-9-7-14(23)8-10-15/h4,6-10,16-19,21,23-26,28H,1,5,11-12H2,2-3H3

> <INCHI_KEY>
ROOOAGWFZPFECL-UHFFFAOYSA-N

> <FORMULA>
C22H30O9

> <MOLECULAR_WEIGHT>
438.473

> <EXACT_MASS>
438.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.66469272351911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.8350365889999996

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.203338126616542

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.820462392018811

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2852411901931382

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
110.59580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate

> <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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.104   5.596   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.564   8.264   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   15   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoic acid	Generator

Chemical Formula

C₂₂H₃₀O₉

Average Mass

438.4730 Da

Monoisotopic Mass

438.18898 Da

IUPAC Name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate

Traditional Name

[3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate

CAS Registry Number

Not Available

SMILES

CC(=CCCC(C)(O)C=C)C(=O)OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H30O9/c1-4-22(3,28)11-5-6-13(2)20(27)29-12-16-17(24)18(25)19(26)21(31-16)30-15-9-7-14(23)8-10-15/h4,6-10,16-19,21,23-26,28H,1,5,11-12H2,2-3H3

InChI Key

ROOOAGWFZPFECL-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
Viburnum phlebotrichum	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
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
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	1.39	ALOGPS
logP	1.84	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	110.6 m³·mol⁻¹	ChemAxon
Polarizability	45.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate (NP0307381)

MOL for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

3D MOL for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

3D SDF for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

3D-SDF for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

PDB for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

3D PDB for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

SMILES for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

INCHI for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

Structure for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)

3D Structure for NP0307381 ([3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl 6-hydroxy-2,6-dimethylocta-2,7-dienoate)