NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate (NP0294761)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 03:27:21 UTC

Updated at

2022-09-10 03:27:22 UTC

NP-MRD ID

NP0294761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

Description

3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate is found in Baccharis sagittalis and Casearia sylvestris. 3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502252D          

 35 37  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    1.4289   -1.6500    0.0000 C   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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    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
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   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
    0.7145   -5.3625    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
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    3.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    3.6134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    2.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5493    2.9137    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 26  1  0  0  0  0
  2 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  4  0  0  0
 32 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 77 79  0  0  0  0  0  0  0  0999 V2000
    3.7028   -2.5962    0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.7668    0.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4231   -2.5739   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518   -2.0235    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073   -0.6366    0.6884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0769   -0.8130    2.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2849   -0.0211    0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -0.7570    0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582   -1.9205    0.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7734   -0.1596    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097   -0.8259    0.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2166    1.0992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3045    0.9969    0.6278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1321    1.7523    1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3728    2.0006    2.7599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0956    0.8295   -0.6754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0622   -0.1472   -0.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0949    0.2838   -1.6915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6931    0.1371   -2.9433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6091   -1.0335   -1.1607 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6861   -1.9234   -1.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684    1.1929   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274    2.1286   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    1.1612   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    0.2442    0.3659 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5330   -0.3913    0.1939 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6566   -0.5597   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012    0.5812    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7909    0.6728    1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729    0.7556    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251    1.8535    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7610    2.1825   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187    3.3360   -1.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2522   -0.3434   -0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642   -1.5201   -0.0339 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4313   -2.3399    1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4194   -3.6667    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -2.7190   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1505   -1.7999    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7616   -2.7467   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187   -3.6051    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4961   -2.6992    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -2.0487   -0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.1923    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -1.8691    2.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -0.3998    2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7878   -1.8402    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4348    1.6586    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0796    1.2266    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4017    2.7293    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9667    2.8997    2.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5099    1.7809   -1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7915   -0.1396   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891    1.0199   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5568   -0.7879   -3.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -1.5013   -1.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2767   -2.8295   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428    1.6472   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002    2.7843   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619    2.6465    0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4296    0.6669   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    1.7837   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629    0.9910    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -1.4388   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9934    0.3065   -1.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -0.8385   -1.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.7090    1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0727    1.6389    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202    1.6149    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522   -0.1045    1.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3585    2.6579    0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6681    2.3912   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145    1.4379   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2612    3.1149   -2.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -0.6145   -1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1978   -0.1660   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6960   -1.2377    0.9158 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  1
  5 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 25 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 34  1  0
 34 35  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 26  2  1  0
  7  5  1  0
 20 11  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  6 44  1  0
  6 45  1  0
  6 46  1  0
 25 63  1  1
 24 61  1  0
 24 62  1  0
 23 59  1  0
 23 60  1  0
 22 58  1  0
 11 47  1  1
 13 48  1  6
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  6
 17 53  1  0
 18 54  1  6
 19 55  1  0
 20 56  1  6
 21 57  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 34 75  1  0
 34 76  1  0
 35 77  1  0
 31 71  1  0
 32 72  1  0
 32 73  1  0
 33 74  1  0
M  END


  Mrv1533004241502252D          

 35 37  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    1.4289   -1.6500    0.0000 C   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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    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
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   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
    0.7145   -5.3625    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
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    3.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    3.6134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    2.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5493    2.9137    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 26  1  0  0  0  0
  2 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  4  0  0  0
 32 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(CCC=C2C(=O)OC2OC(CO)C(O)C(O)C2O)C1(C)CCC(CO)=CCO

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O9/c1-15-7-10-26(3)17(23(33)35-24-22(32)21(31)20(30)18(14-29)34-24)5-4-6-19(26)25(15,2)11-8-16(13-28)9-12-27/h5,9,15,18-22,24,27-32H,4,6-8,10-14H2,1-3H3

> <INCHI_KEY>
LSHAKRWABGHINZ-UHFFFAOYSA-N

> <FORMULA>
C26H42O9

> <MOLECULAR_WEIGHT>
498.613

> <EXACT_MASS>
498.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.071571152495196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
0.9775634583333321

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.188678662240875

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195076028212664

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5275413289946

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
129.04940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.093   2.666   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.630   4.025   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.186   5.331   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.537   6.691   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.076   6.745   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.169   4.079   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.892   5.439   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26    7    2   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   30   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid	Generator

Chemical Formula

C₂₆H₄₂O₉

Average Mass

498.6130 Da

Monoisotopic Mass

498.28288 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCC=C2C(=O)OC2OC(CO)C(O)C(O)C2O)C1(C)CCC(CO)=CCO

InChI Identifier

InChI=1S/C26H42O9/c1-15-7-10-26(3)17(23(33)35-24-22(32)21(31)20(30)18(14-29)34-24)5-4-6-19(26)25(15,2)11-8-16(13-28)9-12-27/h5,9,15,18-22,24,27-32H,4,6-8,10-14H2,1-3H3

InChI Key

LSHAKRWABGHINZ-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
Baccharis sagittalis	LOTUS Database	35616633
Casearia sylvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Clerodane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Fatty alcohol
Fatty acyl
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Oxacycle
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.47	ALOGPS
logP	0.98	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	54.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

75032936

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-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate (NP0294761)

MOL for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D MOL for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D SDF for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D-SDF for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

PDB for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D PDB for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

SMILES for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

INCHI for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

Structure for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D Structure for NP0294761 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-[5-hydroxy-3-(hydroxymethyl)pent-3-en-1-yl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)