NP-MRD: Showing NP-Card for Loxothyrin A (NP0076797)

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Record Information

Version

2.0

Created at

2022-04-28 21:59:20 UTC

Updated at

2022-04-28 21:59:20 UTC

NP-MRD ID

NP0076797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Loxothyrin A

Description

[(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-5-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Loxothyrin A is found in Isodon japonicus, Isodon loxothyrsa and Isodon loxothyrsus. Based on a literature review very few articles have been published on [(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-5-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223592D          

 33 36  0  0  1  0            999 V2000
    1.1824    0.9298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4671    0.4053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6130   -0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -0.9396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742   -0.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476    0.5781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1308    1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9190    1.6261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5240    1.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3408    0.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526    0.0173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3694   -0.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -1.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032    2.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584    2.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687    2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5396    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499    1.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5258    1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    2.7478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939   -0.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    1.5898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3084    2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067    1.8062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3545    2.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  1  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
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  1  0  0  0
  9 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 23  1  6  0  0  0
 23 24  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 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
 30 31  1  0  0  0  0
  1 31  1  0  0  0  0
 31 32  1  1  0  0  0
 29 33  1  6  0  0  0
  2 33  1  6  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
   -4.3001    0.6639    1.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577    0.2290    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1842   -1.0860   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5789   -2.1546    0.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -0.6902   -1.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2082    0.1127   -1.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6524    1.1196   -0.9883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5194    2.0999   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954    1.3948   -1.2281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2332    2.3312   -1.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    0.1956   -0.3634 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0862   -0.4545   -0.0776 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6959   -0.5466   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1601   -1.4291   -2.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549   -1.4684   -2.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1582   -2.2089   -2.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -1.8635    0.4289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3713   -2.9094   -0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641   -3.9705    0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882   -5.0130   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422   -4.0586    1.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -2.2864    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -1.3924    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581    0.0866    1.1502 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5842    0.3766    2.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2242    0.9146    0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    2.2810    0.5962 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    3.1677   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0239    4.6160    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730    2.6542   -0.8764 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    0.2721    1.0044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4501    1.6289    1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683    1.9705    2.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6872    1.6364    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3563   -0.0234    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858   -0.5954   -2.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006    0.3839   -2.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6134    1.5706   -1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350    2.8823   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4106    2.5600    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    1.1109   -2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    3.2689   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    0.4810    0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    0.4076   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824   -1.0348   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -1.9182    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504   -5.0044   -1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188   -6.0291   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -4.8012   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9387   -2.7177   -0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -3.2314    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055   -1.4336    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591   -1.8068    2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -0.4488    3.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526    0.4035    2.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668    1.2939    2.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    0.5602    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1602    0.6358   -0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7246    4.8000    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3381    5.1788   -0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0592    5.0702    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -0.2674    1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    2.4859    1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  2  0
 28 27  1  0
 27 26  1  0
 24 26  1  6
 24 25  1  0
 24 23  1  0
 23 22  1  0
 22 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  2  0
  5 15  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 12 31  1  0
 31 32  1  0
 32 33  2  0
 31 24  1  0
 11 12  1  0
 11  5  1  0
  3  5  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 26 57  1  0
 26 58  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 23 52  1  0
 23 53  1  0
 22 50  1  0
 22 51  1  0
 17 46  1  1
 20 47  1  0
 20 48  1  0
 20 49  1  0
 13 44  1  0
 13 45  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  6
  8 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  0
 11 43  1  1
  1 34  1  0
  1 35  1  0
 31 62  1  1
 32 63  1  0
M  END


  Mrv1652304282223592D          

 33 36  0  0  1  0            999 V2000
    1.1824    0.9298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4671    0.4053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6130   -0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -0.9396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742   -0.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476    0.5781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1308    1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9190    1.6261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5240    1.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3408    0.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526    0.0173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3694   -0.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -1.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032    2.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584    2.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2687    2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5396    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499    1.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5258    1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    2.7478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939   -0.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191    0.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    1.5898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3084    2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067    1.8062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3545    2.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  1  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
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  1  0  0  0
  9 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 23  1  6  0  0  0
 23 24  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 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
 30 31  1  0  0  0  0
  1 31  1  0  0  0  0
 31 32  1  1  0  0  0
 29 33  1  6  0  0  0
  2 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]1(C)CC[C@H](OC(C)=O)[C@]2(COC(=O)[C@]34C[C@H](C[C@@H](O)[C@H]23)C(=C)C4=O)[C@@H]1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O9/c1-12-15-7-16(28)19-23(8-15,20(12)29)21(30)32-11-24(19)17(9-25)22(4,10-31-13(2)26)6-5-18(24)33-14(3)27/h9,15-19,28H,1,5-8,10-11H2,2-4H3/t15-,16+,17+,18-,19-,22-,23+,24-/m0/s1

> <INCHI_KEY>
DESXTEYYECQGPC-QVCHTXSKSA-N

> <FORMULA>
C24H30O9

> <MOLECULAR_WEIGHT>
462.495

> <EXACT_MASS>
462.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.23500175565978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-yl]methyl acetate

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.33892060233333354

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.981086089607583

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.078751775554558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8657558036132134

> <JCHEM_POLAR_SURFACE_AREA>
133.26999999999998

> <JCHEM_REFRACTIVITY>
112.14489999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.207   1.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.872   0.757   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.144  -0.795   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.061  -1.754   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.565  -1.395   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.805  -0.464   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.635   1.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.977   2.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.449   3.035   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.578   1.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.236   0.487   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.765   0.032   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.423  -1.469   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.552  -2.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.024  -2.062   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.210  -4.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.046   4.522   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.456   4.201   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.968   3.911   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.474   2.457   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.987   2.167   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.467   1.291   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.848   3.628   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.190   5.129   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.750   0.351   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.295  -1.090   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.670   1.689   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.209   1.728   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.690   2.968   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.576   3.970   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.066   3.372   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.528   4.840   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.196   1.905   0.000  0.00  0.00           C+0
CONECT    1    2    7   31                                                  
CONECT    2    1    3   25   33                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8   12                                             
CONECT    8    7    9   23                                                  
CONECT    9    8   10   17   18                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    8   24                                                       
CONECT   24   23                                                            
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30    1   32                                                  
CONECT   32   31                                                            
CONECT   33   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
[(1S,1'r,2S,5R,6R,6'r,7'r,9'r)-2-(Acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0,]dodecane]-5-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₉

Average Mass

462.4950 Da

Monoisotopic Mass

462.18898 Da

IUPAC Name

[(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-yl]methyl acetate

Traditional Name

(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]1(C)CC[C@H](OC(C)=O)[C@]2(COC(=O)[C@]34C[C@H](C[C@@H](O)[C@H]23)C(=C)C4=O)[C@@H]1C=O

InChI Identifier

InChI=1S/C24H30O9/c1-12-15-7-16(28)19-23(8-15,20(12)29)21(30)32-11-24(19)17(9-25)22(4,10-31-13(2)26)6-5-18(24)33-14(3)27/h9,15-19,28H,1,5-8,10-11H2,2-4H3/t15-,16+,17+,18-,19-,22-,23+,24-/m0/s1

InChI Key

DESXTEYYECQGPC-QVCHTXSKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Isodon japonicus	Plant	KNApSAcK
Isodon loxothyrsa	Plant	KNApSAcK
Isodon loxothyrsus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Kaurane diterpenoid
Diterpenoid
Diterpene lactone
Tricarboxylic acid or derivatives
Delta_valerolactone
Delta valerolactone
Oxane
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1	ALOGPS
logP	0.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.08	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	133.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.14 m³·mol⁻¹	ChemAxon
Polarizability	46.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163012346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Loxothyrin A (NP0076797)

MOL for NP0076797 (Loxothyrin A)

3D MOL for NP0076797 (Loxothyrin A)

3D SDF for NP0076797 (Loxothyrin A)

3D-SDF for NP0076797 (Loxothyrin A)

PDB for NP0076797 (Loxothyrin A)

3D PDB for NP0076797 (Loxothyrin A)

SMILES for NP0076797 (Loxothyrin A)

INCHI for NP0076797 (Loxothyrin A)

Structure for NP0076797 (Loxothyrin A)

3D Structure for NP0076797 (Loxothyrin A)