NP-MRD: Showing NP-Card for 14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione (NP0317856)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 17:59:14 UTC

Updated at

2022-09-11 17:59:14 UTC

NP-MRD ID

NP0317856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione

Description

14,15,18-Trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]Tricosane-5,19,21-trione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione is found in Schisandra propinqua. 14,15,18-Trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]Tricosane-5,19,21-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514332D          

 41 47  0  0  0  0            999 V2000
    7.1435    3.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729    2.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    1.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2006    2.3522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899    3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401    3.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211    0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    1.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5082    1.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099    0.7290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396   -0.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652   -1.5122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6295   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6622   -1.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9017    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6178   -0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6231    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1701   -1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -2.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902   -1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3031    1.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    2.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    1.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067    1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    2.5758    0.0000 O   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
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
    5.3249    3.7286    1.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1396    2.2527    1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0510    1.5362    1.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3405    0.1361    0.9690 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6046   -0.4024   -0.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1751   -0.5015   -0.2610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8745   -1.9539   -0.6939 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7385   -2.8778    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6553   -1.9536   -1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197   -2.8461   -2.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4776   -0.9862   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7907   -0.6753    0.0041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1167   -1.2921    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2908   -0.5579   -0.1806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2535   -0.2504   -1.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -0.9650   -2.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977   -0.8018   -3.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7009   -2.0449   -1.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5494   -1.3711   -0.0546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6022   -0.4887    0.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1365    0.6926    0.5989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7097    0.7503    2.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7697    1.8325   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3749    3.0832    0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6509    0.6867    0.5922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0124    1.8789   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    1.6501   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    0.7736    0.3740 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5821    1.1528    0.6179 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1805    1.8519   -0.4087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538   -0.1943    0.8316 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7700   -0.2096    2.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868   -1.1250    0.8843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1074   -2.3081   -1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -2.8738   -2.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993   -1.7914   -0.4947 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5120   -1.6900   -1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890   -2.4783    0.6861 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151    0.1167    0.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2203    1.3792    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4156    1.6758    0.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    4.1058    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1617    3.9251    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022    4.2576    1.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336    2.0672    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3142   -0.5035    1.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0077    0.1992   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    0.0967   -1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008   -3.7838    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -2.4333    1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -3.3515    0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.1199   -2.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -1.4935   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -2.3521    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -1.3117    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1366   -2.9742   -1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7734   -2.1477   -1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5191   -2.1658    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9818    0.2993    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8681    1.7992    2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6466    0.1800    2.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8702    1.7679    0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6560    1.7430   -1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3533    3.7779   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271    0.5934    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861    2.2519   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.7034    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    2.6685   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565    1.3514   -1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    0.8127    1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    1.8062    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615    1.9562   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764   -0.5654    2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323   -0.6719   -1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746   -1.9084   -0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -2.4267   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2347   -2.6917    0.9558 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
  4 39  1  0
 39 40  1  0
 40 41  2  0
  4  5  1  0
  5  6  1  0
  6 31  1  0
 31 32  1  1
 31 33  1  0
 33 12  1  0
 12 11  1  6
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  1  1
  7 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 36 38  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  6
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 40  2  1  0
 36  5  1  0
 19 14  1  0
  7  6  1  0
 25 14  1  0
 29 31  1  0
 28 12  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  3 45  1  0
  4 46  1  1
  5 47  1  6
  6 48  1  6
 32 73  1  0
 11 52  1  0
 11 53  1  0
  8 49  1  0
  8 50  1  0
  8 51  1  0
 37 74  1  0
 37 75  1  0
 37 76  1  0
 38 77  1  0
 13 54  1  0
 13 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  1
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  1
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  1
 29 71  1  1
 30 72  1  0
M  END


  Mrv1533004161514332D          

 41 47  0  0  0  0            999 V2000
    7.1435    3.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729    2.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4675    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    1.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2006    2.3522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899    3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401    3.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211    0.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    1.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5082    1.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099    0.7290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7516    0.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396   -0.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652   -1.5122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6295   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124   -0.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6622   -1.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9017    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6178   -0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6231    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1701   -1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -2.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902   -1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3031    1.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    2.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    1.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473    1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993    1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067    1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    2.5758    0.0000 O   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
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(OC1=O)C1C2C3(O)OC4(CC(=O)C2(C)C(=O)C1(C)O)CC12OC(=O)CC1OC(C)(CO)C2CCC4C3O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O12/c1-12-7-14(38-22(12)34)19-20-25(3,23(35)26(19,4)36)16(31)9-27-10-28-15(6-5-13(27)21(33)29(20,37)41-27)24(2,11-30)39-17(28)8-18(32)40-28/h7,13-15,17,19-21,30,33,36-37H,5-6,8-11H2,1-4H3

> <INCHI_KEY>
WCKMMTKBFVRBSL-UHFFFAOYSA-N

> <FORMULA>
C29H36O12

> <MOLECULAR_WEIGHT>
576.595

> <EXACT_MASS>
576.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.96473047582219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.007614195000001045

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.042554715712075

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.815053364697361

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0783025260919077

> <JCHEM_POLAR_SURFACE_AREA>
186.11999999999998

> <JCHEM_REFRACTIVITY>
135.66449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2H-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      13.334   6.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.083   5.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.073   3.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.605   3.139   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.708   4.391   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.621   5.631   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.155   7.098   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.119   1.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.652   1.211   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.432   2.277   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.415   3.462   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.365   1.361   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.136   0.749   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.844  -0.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.354  -1.301   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.588  -2.823   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.642  -0.329   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.892  -1.848   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.103  -0.814   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.569  -2.282   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.016   0.426   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.353  -0.339   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.363   1.173   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.864  -0.196   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.246  -0.168   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.037  -1.604   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.184  -2.891   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.682  -4.349   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.728  -2.397   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.769  -0.835   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.398   0.198   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.200   1.610   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.262   2.095   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.566   3.106   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.547   4.171   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.707   1.367   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.192   2.829   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.635   3.273   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.852   2.363   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.173   3.269   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.223   4.808   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   21                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12   40                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   24   39                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26   30   36                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34   36                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   32   25   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   13   40                                                  
CONECT   40   39   10   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₂

Average Mass

576.5950 Da

Monoisotopic Mass

576.22068 Da

IUPAC Name

14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione

Traditional Name

14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2H-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(OC1=O)C1C2C3(O)OC4(CC(=O)C2(C)C(=O)C1(C)O)CC12OC(=O)CC1OC(C)(CO)C2CCC4C3O

InChI Identifier

InChI=1S/C29H36O12/c1-12-7-14(38-22(12)34)19-20-25(3,23(35)26(19,4)36)16(31)9-27-10-28-15(6-5-13(27)21(33)29(20,37)41-27)24(2,11-30)39-17(28)8-18(32)40-28/h7,13-15,17,19-21,30,33,36-37H,5-6,8-11H2,1-4H3

InChI Key

WCKMMTKBFVRBSL-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
Schisandra propinqua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
11-noriridane monoterpenoid
Monoterpenoid
Furofuran
Oxepane
Acyloin
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Ketone
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	0.21	ALOGPS
logP	-0.0076	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.82	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	186.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.66 m³·mol⁻¹	ChemAxon
Polarizability	57.96 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

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

75254169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione (NP0317856)

MOL for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

3D MOL for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

3D SDF for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

3D-SDF for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

PDB for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

3D PDB for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

SMILES for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

INCHI for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

Structure for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)

3D Structure for NP0317856 (14,15,18-trihydroxy-9-(hydroxymethyl)-9,18,20-trimethyl-17-(4-methyl-5-oxo-2h-furan-2-yl)-4,8,23-trioxahexacyclo[13.7.1.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁶,²⁰]tricosane-5,19,21-trione)