NP-MRD: Showing NP-Card for 2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0286340)

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Record Information

Version

2.0

Created at

2022-09-09 14:52:17 UTC

Updated at

2022-09-09 14:52:17 UTC

NP-MRD ID

NP0286340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-[(3-Hydroxy-6-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-2-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Buddleja japonica, Buddleja officinalis, Bupleurum rigidum, Clinopodium chinense, Clinopodium gracile, Clinopodium micranthum and Verbascum densiflorum. 2-[(3-Hydroxy-6-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-2-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151516342D          

 66 74  0  0  0  0            999 V2000
    5.5779   -3.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0082   -2.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -1.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0442   -0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6499   -0.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -0.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060    0.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5684    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282   -0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520   -0.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0698   -0.7035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114   -1.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -1.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1472    1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803    1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183    1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8690   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2994   -0.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1241   -0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5545    0.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792    0.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8096    1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4152    1.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736   -0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5983   -0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3432   -1.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7376   -1.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5185   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5840   -1.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2633   -1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4825   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0521   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4464   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0161   -4.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913   -4.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2712   -3.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6655   -4.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7016   -3.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5263   -3.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3072   -2.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691   -2.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8330   -2.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2273   -3.1584    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  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 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  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 29  1  0  0  0  0
 22 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 14 33  1  0  0  0  0
 19 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 41 50  1  0  0  0  0
 50 51  1  0  0  0  0
 39 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 56 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 54 63  1  0  0  0  0
 63 64  1  0  0  0  0
 52 65  1  0  0  0  0
  2 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

     RDKit          3D

144152  0  0  0  0  0  0  0  0999 V2000
   -3.4473    1.9124   -3.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740    0.8309   -3.1958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3954    0.1699   -2.2463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0316    1.0713   -1.1875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0394    0.3867   -0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558    0.8729   -0.8650 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2127   -0.1646   -1.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2004   -0.5384   -1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6723   -0.6342   -0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8478   -1.6779    0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4405    0.7664    0.2720 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0914    0.9447    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832    1.0028    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9627   -0.3994    0.8946 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7394   -1.2878    2.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1566   -0.8325   -0.2933 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6092   -2.1877   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9040   -2.3747   -0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847   -1.2104   -0.6891 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6630   -0.4956   -1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500   -0.0883   -2.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7551   -0.1761   -1.1216 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1915   -0.1567   -1.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7242   -1.3829   -2.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1837   -2.6588   -1.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6021   -2.8772   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7347   -3.8319   -2.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6786   -2.6069   -1.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2437   -1.5119   -0.6213 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3483    0.9796   -0.2606 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2957    1.3221    0.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4280   -0.4350    0.5306 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2082   -0.8502    1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802    1.3185    0.2508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6142    1.2782    1.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038    2.8482    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3051    1.1698    0.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0195    2.0576    2.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5984    3.1220    2.7369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8521    4.2463    1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6895    3.7759    0.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8093    3.5994    3.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8849    2.6602    4.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3811    3.8106    3.5484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1534    4.9704    2.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255    2.6294    2.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6766    1.5134    3.5887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4511    0.7707   -1.1484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1506   -0.5507   -1.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0315   -1.4033   -0.5975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7012   -2.2759   -1.4486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8975   -2.5878   -0.7891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8665   -3.3464   -1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4152   -4.5575   -2.0965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6755   -3.2901    0.5077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8598   -3.1360    1.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5592   -2.7650    1.3455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9976   -3.8118    2.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -2.1834    0.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6462   -3.2513    0.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4553    1.3637   -2.5360 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3455    2.7486   -2.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4428    2.8844   -3.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    2.1619   -4.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    1.6841   -4.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915    0.0614   -3.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    1.9137   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004151516342D          

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 61 63  1  0  0  0  0
 54 63  1  0  0  0  0
 63 64  1  0  0  0  0
 52 65  1  0  0  0  0
  2 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2CCC3(C)C(CCC4(C)C3C=CC35OCC6(CCC(C)(C)CC36)C(O)CC45C)C2(C)CO)C(OC2OC(CO)C(O)C(O)C2O)C(OC2OC(CO)C(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C48H78O18/c1-22-30(53)37(65-39-35(58)33(56)31(54)23(18-49)62-39)38(66-40-36(59)34(57)32(55)24(19-50)63-40)41(61-22)64-29-10-11-43(4)25(44(29,5)20-51)8-12-45(6)26(43)9-13-48-27-16-42(2,3)14-15-47(27,21-60-48)28(52)17-46(45,48)7/h9,13,22-41,49-59H,8,10-12,14-21H2,1-7H3

> <INCHI_KEY>
IRJDRINEGANBIK-UHFFFAOYSA-N

> <FORMULA>
C48H78O18

> <MOLECULAR_WEIGHT>
943.134

> <EXACT_MASS>
942.518815672

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
144

> <JCHEM_AVERAGE_POLARIZABILITY>
100.51364713050842

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
-0.3748866943333336

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.377810229291555

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884381477008967

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083576691054

> <JCHEM_POLAR_SURFACE_AREA>
287.14

> <JCHEM_REFRACTIVITY>
230.72200000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      10.412  -5.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.215  -4.504   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.479  -3.152   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.283  -1.838   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.546  -0.485   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.007  -0.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.204  -1.760   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.664  -1.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.928  -0.369   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.125  -1.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.731   0.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.995   2.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.456   2.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.652   1.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.928   2.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.388  -0.330   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.599  -1.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.057  -1.655   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.217  -0.323   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.130  -1.313   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.488  -0.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.066   1.132   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.371   0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.315  -1.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.955  -1.946   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.077  -3.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.901  -3.161   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.350  -1.129   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.295   0.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.275   2.539   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.057   3.866   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.331   2.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.082   1.089   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.991   2.626   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.271   0.906   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.597   1.689   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.363   2.444   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.741   3.132   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.822  -1.877   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.625  -0.563   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      15.165  -0.602   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      15.968   0.712   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      17.508   0.674   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.311   1.987   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      17.575   3.340   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      18.244  -0.679   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      19.784  -0.718   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      17.441  -1.993   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      18.177  -3.346   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      15.901  -1.954   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      16.023  -3.489   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      13.558  -3.229   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      15.098  -3.268   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      15.834  -4.621   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      15.031  -5.935   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      15.767  -7.287   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      14.963  -8.601   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      13.424  -8.562   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      17.306  -7.326   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      18.042  -8.679   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      18.110  -6.012   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      19.649  -6.051   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      17.373  -4.660   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      18.796  -4.069   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      12.755  -4.543   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      13.491  -5.896   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   65                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   29   33                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29   30                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   19   22                                                  
CONECT   30   22   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   14   19   34                                             
CONECT   34   33                                                            
CONECT   35   11    6   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39    4   40   52                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   50                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   43   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   41   51                                                  
CONECT   51   50                                                            
CONECT   52   39   53   65                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   63                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   59                                                  
CONECT   57   56   58                                                       
CONECT   58   57                                                            
CONECT   59   56   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   54   64                                                  
CONECT   64   63                                                            
CONECT   65   52    2   66                                                  
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  148    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₇₈O₁₈

Average Mass

943.1340 Da

Monoisotopic Mass

942.51882 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2CCC3(C)C(CCC4(C)C3C=CC35OCC6(CCC(C)(C)CC36)C(O)CC45C)C2(C)CO)C(OC2OC(CO)C(O)C(O)C2O)C(OC2OC(CO)C(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C48H78O18/c1-22-30(53)37(65-39-35(58)33(56)31(54)23(18-49)62-39)38(66-40-36(59)34(57)32(55)24(19-50)63-40)41(61-22)64-29-10-11-43(4)25(44(29,5)20-51)8-12-45(6)26(43)9-13-48-27-16-42(2,3)14-15-47(27,21-60-48)28(52)17-46(45,48)7/h9,13,22-41,49-59H,8,10-12,14-21H2,1-7H3

InChI Key

IRJDRINEGANBIK-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
Buddleja japonica	LOTUS Database	35616633
Buddleja officinalis	LOTUS Database	35616633
Bupleurum rigidum	LOTUS Database	35616633
Clinopodium chinense	LOTUS Database	35616633
Clinopodium gracile	LOTUS Database	35616633
Clinopodium micranthum	LOTUS Database	35616633
Verbascum densiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxepane
Oxane
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Ether
Dialkyl ether
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	0.84	ALOGPS
logP	-0.37	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	287.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	230.72 m³·mol⁻¹	ChemAxon
Polarizability	100.51 Å³	ChemAxon
Number of Rings	9	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

78178010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

MOL for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0286340 (2-[(5-hydroxy-2-{[2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol)