NP-MRD: Showing NP-Card for 5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one (NP0288739)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 18:34:28 UTC

Updated at

2022-09-09 18:34:28 UTC

NP-MRD ID

NP0288739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one

Description

Agavoside A, also known as agaveside a, 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. Agavoside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, agavoside a has been detected, but not quantified in, green vegetables. 5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one is found in Tribulus terrestris. This could make agavoside a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241218242D          

 42 48  0  0  0  0            999 V2000
    3.5989    0.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989    1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655    2.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221    2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864    2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5466    2.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203    0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412   -0.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412   -1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328   -1.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -1.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020   -1.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742    0.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    1.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342    1.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1107    0.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -0.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342    1.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    1.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -1.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -0.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573    0.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823    0.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8617   -1.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823   -0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -0.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -1.9278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 30  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 29  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 24  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  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
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 31  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
 21 27  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 28  2  0  0  0  0
 26 27  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 38  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 40  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 42  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 94100  0  0  0  0  0  0  0  0999 V2000
   -9.5171   -0.8565    1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7774   -1.4568    0.7600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5423   -2.1883    1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143   -2.0812    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1665   -0.6022   -0.0831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2857    0.1804   -0.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4682   -0.5102   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3485   -0.5971   -1.2347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630    0.3126   -1.0222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0311    0.0540   -1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141    0.7714   -0.6482 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7541    0.2050   -0.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6547   -1.2713   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595   -1.6817   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316   -0.6051   -0.3906 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1491   -1.0551   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0459    0.0888   -0.7093 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9862   -0.4412   -1.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   -0.1968   -1.0344 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8971    0.6470   -1.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0204    1.1313   -1.2639 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4719    2.3701   -1.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3903    3.2797   -1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0288    0.0335   -1.2195 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2178    0.4137   -0.5974 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4556   -1.1169   -0.4396 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6448   -0.9202    0.9369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0438   -1.4557   -0.7784 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9213   -2.3784   -1.8047 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521    1.1922   -1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181    1.7565   -0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316    0.6624    0.3728 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1524    0.6816    1.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0311    0.9335    0.4786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5289    0.5975    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9775    0.1891    1.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581   -0.6281    2.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    0.7721    0.6851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1235    2.1963    1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9846   -0.0784    0.4264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2560   -0.1069    1.0608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8793    1.0978    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0434   -1.6929    2.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3033   -0.1710    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8437   -0.4140    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4502   -2.2547    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7381   -3.2741    1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620   -1.8072    2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9581   -2.4419   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838   -2.6073    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5418   -1.0354   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2860    0.2572   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6826    1.3693   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208    0.5032   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580   -1.0319   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0259    1.8202   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585    0.4836   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9447   -1.7113   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.7426    0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -2.5599   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221   -2.0682    0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -0.3659   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2679   -1.9416   -0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350   -1.4215    0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5566    0.5643    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    0.3628   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7480    1.4247   -0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2860    2.8658   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7842    2.1700   -2.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7436    3.0320   -1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3092   -0.2611   -2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4885    1.3308   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887   -2.0181   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8272    0.0365    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5900   -1.9367    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1718   -3.0254   -1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    0.9256   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036    2.0199   -1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3923    2.1626   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600    2.5889    0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4559    1.1020    2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0284    1.3952    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4232   -0.3246    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    2.0265    0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5428    1.4946    2.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0258   -0.2752    2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0502    2.6223    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008    2.8345    0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483    2.3981    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182   -1.1426    0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2933   -0.9131    1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8241    0.7693    2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2818    1.7836    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3040    1.6313    2.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 41  1  0
 41 40  1  0
 40  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
  9  8  1  0
  5  8  1  6
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2  7  1  0
  7  6  1  0
  5 41  1  0
  6  5  1  0
 38 40  1  0
 28 19  1  0
 38 11  1  0
 34 12  1  0
 32 15  1  0
 42 92  1  0
 42 93  1  0
 42 94  1  0
 41 91  1  1
 40 90  1  6
  9 53  1  1
 10 54  1  0
 10 55  1  0
 11 56  1  6
 12 57  1  6
 13 58  1  0
 13 59  1  0
 14 60  1  0
 14 61  1  0
 15 62  1  6
 16 63  1  0
 16 64  1  0
 17 65  1  1
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  6
 35 85  1  0
 35 86  1  0
 39 87  1  0
 39 88  1  0
 39 89  1  0
 19 66  1  1
 21 67  1  1
 22 68  1  0
 22 69  1  0
 23 70  1  0
 24 71  1  6
 25 72  1  0
 26 73  1  6
 27 74  1  0
 28 75  1  1
 29 76  1  0
  4 49  1  0
  4 50  1  0
  3 47  1  0
  3 48  1  0
  2 46  1  6
  1 43  1  0
  1 44  1  0
  1 45  1  0
  7 51  1  0
  7 52  1  0
M  END


  Mrv0541 02241218242D          

 42 48  0  0  0  0            999 V2000
    3.5989    0.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989    1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655    2.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9221    2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5864    2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5466    2.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    1.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203    0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412   -0.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412   -1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328   -1.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -1.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020   -1.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742    0.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    1.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342    1.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1107    0.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -0.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342    1.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    1.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -1.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -0.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573    0.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823    0.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8617   -1.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823   -0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -0.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -1.9278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 30  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 29  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 24  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  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
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 31  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
 21 27  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 28  2  0  0  0  0
 26 27  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 38  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 40  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 42  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(CCC5(C)C4CC(=O)C23C)OC2OC(CO)C(O)C(O)C2O)OC11CCC(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O9/c1-16-7-10-33(39-15-16)17(2)26-23(42-33)12-22-20-6-5-18-11-19(40-30-29(38)28(37)27(36)24(14-34)41-30)8-9-31(18,3)21(20)13-25(35)32(22,26)4/h16-24,26-30,34,36-38H,5-15H2,1-4H3

> <INCHI_KEY>
NVCUAFIUMZCPGV-UHFFFAOYSA-N

> <FORMULA>
C33H52O9

> <MOLECULAR_WEIGHT>
592.7606

> <EXACT_MASS>
592.361133262

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
67.29705270290992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.894765928333333

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.20009577112403

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210576079649119

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083541525649

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
152.52239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one

> <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  O   UNK     0       6.718   0.851   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.718   2.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.538   3.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.776   4.838   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.188   4.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.428   5.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.754   4.317   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   2.856   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.348   1.601   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.265   0.363   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.369  -0.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.903  -0.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.570  -1.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.570  -2.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.248  -3.514   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.072  -2.751   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.423  -3.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.737  -2.772   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.737  -1.254   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.423  -0.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.072  -1.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.072   0.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.036   2.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.903   1.113   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.557   1.891   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.207   1.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.240  -0.435   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.557   3.413   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.362   2.692   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.125   1.778   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.093  -3.555   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.407  -2.795   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.407  -1.277   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.760  -0.494   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.760   1.023   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.114   1.804   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -7.760  -5.139   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.760  -3.576   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.075  -2.818   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.114  -1.277   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -10.428  -0.517   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -10.428  -3.598   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    8   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    2    7    9                                                  
CONECT    9    8   10   24                                                  
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20   22   27                                             
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24    9   12   23   25                                             
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   13   21   26                                                  
CONECT   28   25                                                            
CONECT   29    5   30                                                       
CONECT   30    2   29                                                       
CONECT   31   18   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   32   37   39                                                  
CONECT   39   38   40   42                                                  
CONECT   40   34   39   41                                                  
CONECT   41   40                                                            
CONECT   42   39                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Agaveside a	HMDB
Agavosid a	HMDB

Chemical Formula

C₃₃H₅₂O₉

Average Mass

592.7606 Da

Monoisotopic Mass

592.36113 Da

IUPAC Name

5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one

Traditional Name

5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CCC5CC(CCC5(C)C4CC(=O)C23C)OC2OC(CO)C(O)C(O)C2O)OC11CCC(C)CO1

InChI Identifier

InChI=1S/C33H52O9/c1-16-7-10-33(39-15-16)17(2)26-23(42-33)12-22-20-6-5-18-11-19(40-30-29(38)28(37)27(36)24(14-34)41-30)8-9-31(18,3)21(20)13-25(35)32(22,26)4/h16-24,26-30,34,36-38H,5-15H2,1-4H3

InChI Key

NVCUAFIUMZCPGV-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
Tribulus terrestris	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

Substituents

Steroidal saponin
Triterpenoid
Spirostane skeleton
12-oxosteroid
Oxosteroid
Glycosyl compound
O-glycosyl compound
Ketal
Monosaccharide
Oxane
Tetrahydrofuran
Secondary alcohol
Ketone
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.98	ALOGPS
logP	2.89	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	152.52 m³·mol⁻¹	ChemAxon
Polarizability	67.3 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034391

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012777

KNApSAcK ID

C00003562

Chemspider ID

3680898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4483033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one (NP0288739)

MOL for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

3D MOL for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

3D SDF for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

3D-SDF for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

PDB for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

3D PDB for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

SMILES for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

INCHI for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

Structure for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)

3D Structure for NP0288739 (5,7',9',13'-tetramethyl-16'-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-10'-one)