NP-MRD: Showing NP-Card for 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate (NP0278308)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-09 03:16:58 UTC

Updated at

2022-09-09 03:16:58 UTC

NP-MRD ID

NP0278308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate

Description

AC1L903B belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate is found in Quassia undulata. AC1L903B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503092D          

 35 39  0  0  0  0            999 V2000
    1.2460   -4.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888   -3.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238   -3.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7159   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -2.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -2.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8015   -2.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1486   -1.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -1.5220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473   -1.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    0.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714    2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    1.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    1.0746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2229   -0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    0.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580    0.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    0.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3143    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -0.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7342    0.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -1.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  8 35  1  0  0  0  0
 26 35  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    7.2805    1.0695    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    0.6447   -0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9131    0.6603    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8399    1.0919    1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869    0.2556   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7143   -0.1229   -1.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4594    0.2537    0.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -0.1314   -0.5636 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6646   -1.3374    0.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6728   -1.4387    1.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -0.5064    2.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667   -2.5881    2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -3.5918    1.0145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9699   -4.6383    1.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -2.7941    0.2209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2692   -2.2482    1.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6945   -1.6435   -0.5296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4762   -2.2126   -1.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949   -0.4858   -0.4609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8008   -0.6207   -1.3919 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3673   -1.8714   -1.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -0.2787   -2.6215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305    0.7077   -2.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578    0.8178   -0.9518 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3690    1.0740   -0.7036 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6515    1.9394    0.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    2.3220    1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    2.6318    2.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6918    2.3747    0.9295 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0690    3.7250    1.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    1.9727   -0.4865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3685    1.7730   -0.8233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3115    2.4774    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219    0.3589   -0.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9652    0.2244   -1.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4565    0.3563    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1384    2.0739    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1225    1.0300   -0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1144    0.3223   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8273    1.1434    1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2424    0.3339    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2879    2.0606    1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5505   -0.4140   -1.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3128   -2.2060   -0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    0.2950    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371   -1.0591    3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2247   -0.0579    3.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1135   -2.8011    3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274   -3.9294    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -5.1609    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677   -3.5117   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -2.9049    1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561   -1.6574   -2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149   -3.2186   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -2.4506   -2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9979   -0.3757    0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3700   -1.8381   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.6534   -2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    0.5831   -3.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    1.6705   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    1.8054    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983    4.3200    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    2.8386   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    2.2365   -1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542    2.2790   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2878    2.0063    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1941    3.5598    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891    0.0387    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    1.1143   -1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 24 23  1  6
 24 19  1  0
 19 17  1  0
 17 18  1  6
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  1  0
 24 25  1  0
  9 17  1  0
 24 31  1  0
 19 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  6
 25 60  1  6
 29 61  1  1
 30 62  1  0
 31 63  1  6
 32 64  1  6
 33 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  1
 35 69  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 19 56  1  1
 18 53  1  0
 18 54  1  0
 18 55  1  0
 15 51  1  6
 16 52  1  0
 13 49  1  6
 14 50  1  0
 12 48  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
  9 44  1  6
M  END


  Mrv1533004241503092D          

 35 39  0  0  0  0            999 V2000
    1.2460   -4.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2888   -3.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238   -3.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7159   -3.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -2.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745   -2.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8015   -2.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1486   -1.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -1.5220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -1.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0473   -1.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    0.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938    1.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714    2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    1.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    1.0746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    0.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2229   -0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    0.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580    0.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    0.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3143    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -0.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7342    0.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0062   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -1.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  8 35  1  0  0  0  0
 26 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1C2OC(=O)C(O)C3C(C)C(O)C4(O)OCC23C4C2(C)C(O)C(O)C=C(C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O10/c1-6-9(2)20(30)34-16-13-10(3)7-12(26)18(29)23(13,5)22-24-8-33-25(22,32)17(28)11(4)14(24)15(27)21(31)35-19(16)24/h6-7,11-19,22,26-29,32H,8H2,1-5H3

> <INCHI_KEY>
OMOJVYZMOHWBDG-UHFFFAOYSA-N

> <FORMULA>
C25H34O10

> <MOLECULAR_WEIGHT>
494.537

> <EXACT_MASS>
494.215197295

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.57237274562247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
-0.17587884466666664

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.388251729158426

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.883576647514971

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3190270896253775

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
120.25230000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.326  -8.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.406  -7.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.778  -6.520   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.070  -7.358   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.858  -4.982   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.566  -4.144   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.230  -4.282   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.310  -2.744   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.011  -1.911   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.754  -2.841   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.353  -2.213   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.088  -3.091   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.253  -0.684   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.121   0.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.560   0.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.224   1.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.755   2.108   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.348   2.670   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.120   4.193   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.764   2.001   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.099   3.504   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.229   2.006   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.068   0.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.149  -0.303   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.140   0.223   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.695  -0.515   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.642   1.024   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.037   0.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.053   1.780   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.362  -0.545   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.704   0.211   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.345  -2.085   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.003  -2.840   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.986  -4.380   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.678  -2.055   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   25                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    9   15   25                                             
CONECT   25   24   20   26                                                  
CONECT   26   25   27   28   35                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    8   26                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₁₀

Average Mass

494.5370 Da

Monoisotopic Mass

494.21520 Da

IUPAC Name

4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate

Traditional Name

4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C2OC(=O)C(O)C3C(C)C(O)C4(O)OCC23C4C2(C)C(O)C(O)C=C(C)C12

InChI Identifier

InChI=1S/C25H34O10/c1-6-9(2)20(30)34-16-13-10(3)7-12(26)18(29)23(13,5)22-24-8-33-25(22,32)17(28)11(4)14(24)15(27)21(31)35-19(16)24/h6-7,11-19,22,26-29,32H,8H2,1-5H3

InChI Key

OMOJVYZMOHWBDG-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
Quassia undulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Pyran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.67	ALOGPS
logP	-0.18	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.25 m³·mol⁻¹	ChemAxon
Polarizability	49.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

435724

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate (NP0278308)

MOL for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

3D MOL for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

3D SDF for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

3D-SDF for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

PDB for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

3D PDB for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

SMILES for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

INCHI for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

Structure for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)

3D Structure for NP0278308 (4,5,8,16,17-pentahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-12-yl 2-methylbut-2-enoate)