NP-MRD: Showing NP-Card for 4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one (NP0272145)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 18:39:50 UTC

Updated at

2022-09-08 18:39:50 UTC

NP-MRD ID

NP0272145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

Description

4,5,7,8,17-Pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-14-en-9-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one is found in Eurycoma longifolia. 4,5,7,8,17-Pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadec-14-en-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500152D          

 40 45  0  0  0  0            999 V2000
    4.2776   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153   -0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7343    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0339    1.3579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432    2.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334    2.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427    3.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7623    2.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7716    3.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4720    2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911    2.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627    1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725    0.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    0.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441   -1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647    0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    0.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    1.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    1.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504    0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -0.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 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  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 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
 38 39  1  0  0  0  0
 23 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 19 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -5.3130   -0.9183    2.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4303   -0.9098    1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462   -2.1060    1.6352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0535   -2.9273    0.6590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1369   -1.5993    1.2928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2515   -2.6477    1.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7876   -0.7205    2.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510    0.5257    2.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8480    0.5098    0.5902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5389    1.7289   -0.1489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8593    1.6205   -1.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696    0.2717   -1.9351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3079    0.3575   -2.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.7359   -4.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389    0.1118   -2.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088   -0.2652   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4693    0.3214   -0.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4637   -0.5832   -0.3197 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5172   -0.3389   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093    0.4561   -0.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5786    0.7746   -1.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5372    1.5884   -1.0589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1879   -0.0352    0.5654 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6444    1.0973    1.2798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2290   -0.7532    1.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5177   -0.5650    2.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8289   -0.3215    1.1278 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7192    1.0300    1.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1352   -0.0753   -0.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5250   -0.7120    1.0271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683   -0.6537   -0.7785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8195   -2.0160   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.7705    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7001    2.5149   -0.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6793    2.6083    0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356    3.7035    0.8490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623    1.4070    1.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4424    1.2086    1.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408    0.2402    0.8223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9505   -0.1460   -0.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0108   -0.1193    2.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804   -1.7734    3.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4960   -2.6118    2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4633   -3.7605    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877   -2.9737    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055    1.2534    2.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755    0.8311    2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701    2.3685    0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    2.2602   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914    2.0721   -2.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489   -0.1940   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713    0.0352   -4.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751    0.6335   -4.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802    1.7977   -4.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084    0.2008   -3.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -1.3675   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -1.6342   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449    1.4500   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1160    1.4213   -2.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0267   -0.1396   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1245    2.4746   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -0.6579    0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5515    0.9534    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439   -1.8559    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098   -0.5945    2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -0.9447    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772    1.1416    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258    1.0106   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8408   -0.1126    1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0935   -2.6188   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631   -1.9095   -2.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -2.6092   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681   -1.2661   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863    1.5422    2.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6822    1.4995    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411    0.4502   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  6
 31 33  1  0
 33  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  6
 39  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 12 13  1  0
 27 18  1  0
 12 31  1  0
  9 33  1  0
 39  9  1  0
  3  5  1  0
 14 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  6
 18 57  1  1
 20 58  1  1
 21 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  6
 24 63  1  0
 25 64  1  6
 26 65  1  0
 27 66  1  1
 28 67  1  0
 29 68  1  1
 30 69  1  0
 32 70  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  6
  6 45  1  0
  8 46  1  0
  8 47  1  0
 10 48  1  1
 11 49  1  0
 11 50  1  0
 12 51  1  6
 37 74  1  1
 38 75  1  0
 40 76  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  1
  4 44  1  0
M  END


  Mrv1533004201500152D          

 40 45  0  0  0  0            999 V2000
    4.2776   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153   -0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7343    0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0339    1.3579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432    2.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3334    2.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427    3.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7623    2.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7716    3.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4720    2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911    2.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627    1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725    0.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055    0.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    0.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441   -1.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -1.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647    0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    0.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    1.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710    2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5522    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    1.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2504    0.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -0.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 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  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 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
 38 39  1  0  0  0  0
 23 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 19 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(OC2OC(CO)C(O)C(O)C2O)C(O)C2(C)C3C4(O)OCC33C(CC12)OC(=O)C(O)C3(O)C(=C)C4O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O14/c1-8-4-11(38-21-16(30)15(29)14(28)12(6-27)39-21)18(32)23(3)10(8)5-13-24-7-37-26(36,22(23)24)17(31)9(2)25(24,35)19(33)20(34)40-13/h4,10-19,21-22,27-33,35-36H,2,5-7H2,1,3H3

> <INCHI_KEY>
XWUBEYICEUBFTO-UHFFFAOYSA-N

> <FORMULA>
C26H36O14

> <MOLECULAR_WEIGHT>
572.56

> <EXACT_MASS>
572.210505839

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.35291891564217

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

> <ALOGPS_LOGP>
-1.38

> <JCHEM_LOGP>
-4.201925043999998

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.46749050078348

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.70989604077283

> <JCHEM_PKA_STRONGEST_BASIC>
-3.387262392617761

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
128.39489999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       7.985  -4.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -2.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.344  -2.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.362  -0.545   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.704   0.210   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.721   1.750   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.397   2.535   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.414   4.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.089   4.860   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.106   6.399   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.756   4.830   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.774   6.369   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.081   4.045   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.423   4.799   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.064   2.505   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.389   1.720   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.037   0.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.054   1.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.695  -0.515   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.642   1.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.677  -2.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.309  -2.744   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.010  -1.911   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.753  -2.841   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.352  -2.213   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.087  -3.091   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.253  -0.685   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.121   0.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.560   0.152   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.136   0.738   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.225   1.645   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.756   2.107   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.348   2.670   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.119   4.193   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.764   2.002   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.098   3.505   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.230   2.007   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.067   0.438   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.149  -0.303   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.141   0.224   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   40                                             
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   39                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   39                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37   40                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   23   29   40                                             
CONECT   40   39   19   35                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₄

Average Mass

572.5600 Da

Monoisotopic Mass

572.21051 Da

IUPAC Name

4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

Traditional Name

4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

CAS Registry Number

Not Available

SMILES

CC1=CC(OC2OC(CO)C(O)C(O)C2O)C(O)C2(C)C3C4(O)OCC33C(CC12)OC(=O)C(O)C3(O)C(=C)C4O

InChI Identifier

InChI=1S/C26H36O14/c1-8-4-11(38-21-16(30)15(29)14(28)12(6-27)39-21)18(32)23(3)10(8)5-13-24-7-37-26(36,22(23)24)17(31)9(2)25(24,35)19(33)20(34)40-13/h4,10-19,21-22,27-33,35-36H,2,5-7H2,1,3H3

InChI Key

XWUBEYICEUBFTO-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
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Para-dioxane
Gamma butyrolactone
Tetrahydrofuran
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-4.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.71	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	128.39 m³·mol⁻¹	ChemAxon
Polarizability	55.35 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14396861

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one (NP0272145)

MOL for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D MOL for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D SDF for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D-SDF for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

PDB for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D PDB for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

SMILES for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

INCHI for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

Structure for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D Structure for NP0272145 (4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)