NP-MRD: Showing NP-Card for 2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0218967)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 19:48:06 UTC

Updated at

2022-09-05 19:48:06 UTC

NP-MRD ID

NP0218967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(3B,5b,22a,25R)-Furostane-22-methoxy-3,26-diol 3-[glucosyl-(1->2)-glucoside] 26-glucoside belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative (3b,5b,22a,25R)-Furostane-22-methoxy-3,26-diol 3-[glucosyl-(1->2)-glucoside] 26-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3b,5b,22a,25R)-furostane-22-methoxy-3,26-diol 3-[glucosyl-(1->2)-glucoside] 26-glucoside has been detected, but not quantified in, green vegetables. 2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Anemarrhena asphodeloides and Asparagus africanus. This could make (3b,5b,22a,25R)-furostane-22-methoxy-3,26-diol 3-[glucosyl-(1->2)-glucoside] 26-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211482D          

 65 72  0  0  0  0            999 V2000
   -4.0605    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0605    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    2.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    2.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7658    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    2.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    2.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    3.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7658    3.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    3.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    4.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054    3.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    3.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    3.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5009    3.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1491    3.4653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    4.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    4.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    4.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473    3.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1648    2.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630    2.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5438    2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3263    3.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    3.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3106    4.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9070    4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3419    2.6217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1804    1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5996    0.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106   -0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -1.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651   -1.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -2.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6262   -1.7313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6262   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3419   -0.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591   -2.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504   -3.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -2.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504   -1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -4.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -3.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -1.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558   -0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 22  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
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 19 31  1  0  0  0  0
 20 24  1  0  0  0  0
 21 44  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 29 33  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 42  1  0  0  0  0
 36 37  1  0  0  0  0
 36 41  1  0  0  0  0
 37 38  1  0  0  0  0
 37 40  1  0  0  0  0
 38 39  1  0  0  0  0
 42 43  1  0  0  0  0
 44 45  1  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 53  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 48 49  1  0  0  0  0
 48 51  1  0  0  0  0
 49 50  1  0  0  0  0
 50 55  1  0  0  0  0
 53 54  1  0  0  0  0
 55 56  1  0  0  0  0
 55 60  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 61  1  0  0  0  0
 58 59  1  0  0  0  0
 58 63  1  0  0  0  0
 59 60  1  0  0  0  0
 59 64  1  0  0  0  0
 60 65  1  0  0  0  0
 61 62  1  0  0  0  0
M  END


  Mrv0541 02241211482D          

 65 72  0  0  0  0            999 V2000
   -4.0605    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0605    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    1.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    2.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    2.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7658    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855    2.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    2.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    3.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7658    3.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948    3.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    4.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054    3.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    3.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    3.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5009    3.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1491    3.4653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453    4.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    4.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    4.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9473    3.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1648    2.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630    2.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5438    2.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3263    3.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281    3.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3106    4.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9070    4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3419    2.6217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1804    1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5996    0.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106   -0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9106   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -1.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651   -1.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1950   -2.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6262   -1.7313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6262   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3419   -0.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591   -2.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504   -3.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -2.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504   -1.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3531   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -4.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -3.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149   -1.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558   -0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 22  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
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 19 31  1  0  0  0  0
 20 24  1  0  0  0  0
 21 44  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 29 33  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 42  1  0  0  0  0
 36 37  1  0  0  0  0
 36 41  1  0  0  0  0
 37 38  1  0  0  0  0
 37 40  1  0  0  0  0
 38 39  1  0  0  0  0
 42 43  1  0  0  0  0
 44 45  1  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 53  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 48 49  1  0  0  0  0
 48 51  1  0  0  0  0
 49 50  1  0  0  0  0
 50 55  1  0  0  0  0
 53 54  1  0  0  0  0
 55 56  1  0  0  0  0
 55 60  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 61  1  0  0  0  0
 58 59  1  0  0  0  0
 58 63  1  0  0  0  0
 59 60  1  0  0  0  0
 59 64  1  0  0  0  0
 60 65  1  0  0  0  0
 61 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(CCC(C)COC2OC(CO)C(O)C(O)C2O)OC2CC3C4CCC5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C46H78O19/c1-20(19-59-41-38(56)35(53)32(50)28(16-47)61-41)8-13-46(58-5)21(2)31-27(65-46)15-26-24-7-6-22-14-23(9-11-44(22,3)25(24)10-12-45(26,31)4)60-43-40(37(55)34(52)30(18-49)63-43)64-42-39(57)36(54)33(51)29(17-48)62-42/h20-43,47-57H,6-19H2,1-5H3

> <INCHI_KEY>
FDASUPFDHLZNSK-UHFFFAOYSA-N

> <FORMULA>
C46H78O19

> <MOLECULAR_WEIGHT>
935.1001

> <EXACT_MASS>
934.513730314

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
100.50137273995252

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.4981990703333292

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.313559223824825

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.847561668842067

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483772987566265

> <JCHEM_POLAR_SURFACE_AREA>
296.36999999999995

> <JCHEM_REFRACTIVITY>
224.9171000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.580   2.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.580   0.624   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.246  -0.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.916   0.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.916   2.166   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.246   2.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.582  -0.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.252   0.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.252   2.166   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.582   2.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.924   2.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.924   4.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.252   5.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.582   4.467   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.533   2.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.429   3.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.533   4.938   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.878   4.172   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.878   5.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.429   6.165   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.895  -0.146   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.916   3.702   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.924   6.019   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.608   7.591   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.117   6.409   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.404   5.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.991   6.584   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.402   5.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.612   6.469   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.991   8.187   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.878   7.591   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.543   8.362   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.102   6.070   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.508   4.583   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.998   4.190   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.082   5.284   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.676   6.769   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.186   7.160   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.780   8.647   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      14.760   7.863   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      15.572   4.894   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      13.403   2.702   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      12.319   1.608   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -10.231  -0.917   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -11.564  -0.146   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0     -12.900  -0.917   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -12.900  -2.461   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -11.564  -3.234   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -10.231  -2.461   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -8.895  -3.229   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -11.564  -4.776   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -14.236  -3.232   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -14.236  -0.146   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -15.572  -0.917   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -7.559  -4.000   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -7.577  -5.541   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -6.254  -6.330   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -4.913  -5.541   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -4.913  -4.000   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -6.254  -3.214   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -6.259  -7.871   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -4.926  -8.647   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -3.574  -6.307   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -3.574  -3.234   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -6.264  -1.672   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   12   16   20                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20   25   31                                             
CONECT   20   17   19   24                                                  
CONECT   21    2   44                                                       
CONECT   22    5                                                            
CONECT   23   12                                                            
CONECT   24   20                                                            
CONECT   25   19   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   33                                                       
CONECT   30   27                                                            
CONECT   31   19   32                                                       
CONECT   32   31                                                            
CONECT   33   29   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   42                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   40                                                  
CONECT   38   33   37   39                                                  
CONECT   39   38                                                            
CONECT   40   37                                                            
CONECT   41   36                                                            
CONECT   42   35   43                                                       
CONECT   43   42                                                            
CONECT   44   21   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   53                                                  
CONECT   47   46   48   52                                                  
CONECT   48   47   49   51                                                  
CONECT   49   44   48   50                                                  
CONECT   50   49   55                                                       
CONECT   51   48                                                            
CONECT   52   47                                                            
CONECT   53   46   54                                                       
CONECT   54   53                                                            
CONECT   55   50   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   61                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60   64                                                  
CONECT   60   55   59   65                                                  
CONECT   61   57   62                                                       
CONECT   62   61                                                            
CONECT   63   58                                                            
CONECT   64   59                                                            
CONECT   65   60                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₇₈O₁₉

Average Mass

935.1001 Da

Monoisotopic Mass

934.51373 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1(CCC(C)COC2OC(CO)C(O)C(O)C2O)OC2CC3C4CCC5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C46H78O19/c1-20(19-59-41-38(56)35(53)32(50)28(16-47)61-41)8-13-46(58-5)21(2)31-27(65-46)15-26-24-7-6-22-14-23(9-11-44(22,3)25(24)10-12-45(26,31)4)60-43-40(37(55)34(52)30(18-49)63-43)64-42-39(57)36(54)33(51)29(17-48)62-42/h20-43,47-57H,6-19H2,1-5H3

InChI Key

FDASUPFDHLZNSK-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
Anemarrhena asphodeloides	LOTUS Database	35616633
Asparagus africanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Not Available

Substituents

Not Available

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	-0.02	ALOGPS
logP	-0.5	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	296.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	224.92 m³·mol⁻¹	ChemAxon
Polarizability	100.5 Å³	ChemAxon
Number of Rings	8	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

HMDB0034375

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012749

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

74029732

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0218967)

MOL for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0218967 (2-[4-(16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)