NP-MRD: Showing NP-Card for (2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0274093)

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Record Information

Version

2.0

Created at

2022-09-08 21:21:04 UTC

Updated at

2022-09-08 21:21:04 UTC

NP-MRD ID

NP0274093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

Description

Ligustrin C belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate is found in Ligustrum ovalifolium. Based on a literature review very few articles have been published on Ligustrin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082223212D          

 59 64  0  0  1  0            999 V2000
    4.2868  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -15.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1473  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -16.0875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5762  -15.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -16.5000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1473  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -17.3250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762  -18.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -16.5000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2907  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -17.7375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.4341  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4308  -16.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9611  -17.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -18.5625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7197  -19.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -19.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -19.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -20.6250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.7197  -21.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -21.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -22.2750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.4341  -23.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -21.8625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.8631  -22.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -21.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.8631  -20.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -17.7375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9552  -18.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9956  -16.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6083  -16.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  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
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 44 43  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  6  0  0  0
 40 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 32 55  1  0  0  0  0
 27 55  1  0  0  0  0
 55 56  1  6  0  0  0
 24 57  1  0  0  0  0
 19 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
M  END

     RDKit          3D

145150  0  0  0  0  0  0  0  0999 V2000
   16.7866   -0.7885    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7042   -1.1693    0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3308   -1.0511    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0508    0.3665    1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1207    1.3607    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1491    1.1180   -1.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7161    1.1380   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8317    0.9064   -1.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3562    0.9165   -1.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0059   -0.1462   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961   -0.0715   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559    1.2275    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392    1.4318    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    0.5838    1.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895   -0.8662    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1346   -1.1386    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -1.3820   -0.6860 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463   -1.1245    0.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -1.3645   -0.6449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1178   -2.6205   -0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -2.4608   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980   -1.2449    0.0759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5539   -1.4242    1.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759   -0.0562   -0.6208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6953    1.2110    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1917    1.3804   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878    0.1632    0.2195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1988    0.2170    1.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -1.1280   -0.2463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2192   -2.2854    0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6264   -1.9215    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2055   -0.7565    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5762   -0.3761    0.3820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5278   -1.4391    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2880   -2.0729   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5892   -3.2840   -0.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5764   -2.6527    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7238   -1.1813   -1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6640   -0.1876   -1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1901    0.5594   -0.5961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3577    1.2710   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3603    2.5396    0.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4895    0.6251    0.3511 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6060    1.2590    0.9136 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.9550    0.8396    2.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6656    1.8649    2.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.6337    3.1013    2.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3741    0.2010   -2.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    1.0495   -0.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5953   -1.1783    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7362   -1.2439    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9376    0.3252    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9124   -2.2321   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8113   -0.5368   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2566   -1.6994    1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5963   -1.4183    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8920    0.6299    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1411    0.4445    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0169    2.4066    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1445    1.3405   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4127    0.2309   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2629    2.0052   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5893    0.3604    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5117    2.1629   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0327    1.6309   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0466   -0.1020   -2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7851    1.4002    1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4774    2.0980   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6470    2.5495    1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1767    1.4596   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4593    0.8278    2.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993    1.0085    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -1.5410    1.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1222   -1.1646    2.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6556   -1.5423   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3915   -3.1568    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -3.3655   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082223212D          

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M  END
> <DATABASE_ID>
NP0274093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C51H86O8/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-41(53)58-40-26-27-48(6)38(47(40,4)5)25-28-50(8)39(48)24-23-35-36-33-46(2,3)29-31-51(36,32-30-49(35,50)7)45(56)59-44-43(55)42(54)37(52)34-57-44/h23,36-40,42-44,52,54-55H,9-22,24-34H2,1-8H3/t36-,37-,38-,39+,40-,42-,43+,44-,48-,49+,50+,51-/m0/s1

> <INCHI_KEY>
WGBZLFHDGZSXIP-LHVWMRNKSA-N

> <FORMULA>
C51H86O8

> <MOLECULAR_WEIGHT>
827.241

> <EXACT_MASS>
826.632269729

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
145

> <JCHEM_AVERAGE_POLARIZABILITY>
102.56057964558562

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <JCHEM_LOGP>
11.878154184333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.398466509761196

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.230696701263165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526600778472554

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000002

> <JCHEM_REFRACTIVITY>
233.68460000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002 -27.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336 -28.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669 -27.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -28.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337 -27.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.670 -28.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.005 -28.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.339 -27.720   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.673 -28.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.006 -27.720   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.340 -28.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.674 -27.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.007 -28.490   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.007 -30.030   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      29.341 -27.720   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      30.675 -28.490   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.008 -27.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.342 -28.490   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.342 -30.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.676 -29.260   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.008 -30.800   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.008 -32.340   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      33.342 -33.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      34.676 -32.340   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.676 -33.880   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.676 -30.800   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.009 -30.030   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.343 -30.800   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      37.343 -32.340   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      38.677 -33.110   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      40.010 -32.340   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      41.344 -33.110   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      41.871 -31.663   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      42.861 -33.377   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      41.344 -34.650   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      40.010 -35.420   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      38.677 -34.650   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      38.677 -36.190   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      37.343 -36.960   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      40.010 -36.960   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      40.010 -38.500   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      38.677 -39.270   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      38.677 -40.810   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      40.010 -41.580   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      40.010 -43.120   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      41.344 -40.810   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      42.678 -41.580   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      41.344 -39.270   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      42.678 -38.500   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      37.343 -35.420   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      36.009 -34.650   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      36.009 -33.110   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      35.383 -34.517   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      30.675 -30.030   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      29.859 -31.336   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      29.136 -30.084   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   57                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25   57                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   55                                             
CONECT   28   27                                                            
CONECT   29   27   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   55                                                  
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33   41   53                                             
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   51                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51                                                            
CONECT   53   40   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   32   27   56                                             
CONECT   56   55                                                            
CONECT   57   24   19   58   59                                             
CONECT   58   57                                                            
CONECT   59   57                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₈₆O₈

Average Mass

827.2410 Da

Monoisotopic Mass

826.63227 Da

IUPAC Name

(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)C1(C)C

InChI Identifier

InChI=1S/C51H86O8/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-41(53)58-40-26-27-48(6)38(47(40,4)5)25-28-50(8)39(48)24-23-35-36-33-46(2,3)29-31-51(36,32-30-49(35,50)7)45(56)59-44-43(55)42(54)37(52)34-57-44/h23,36-40,42-44,52,54-55H,9-22,24-34H2,1-8H3/t36-,37-,38-,39+,40-,42-,43+,44-,48-,49+,50+,51-/m0/s1

InChI Key

WGBZLFHDGZSXIP-LHVWMRNKSA-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
Ligustrum ovalifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	11.88	ChemAxon
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	233.68 m³·mol⁻¹	ChemAxon
Polarizability	102.56 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	Yes	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

101938476

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0274093)

MOL for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D MOL for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D SDF for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D-SDF for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

PDB for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D PDB for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

SMILES for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

INCHI for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

Structure for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D Structure for NP0274093 ((2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl (4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(hexadecanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)