NP-MRD: Showing NP-Card for 7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate (NP0310621)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 06:04:17 UTC

Updated at

2022-09-11 06:04:18 UTC

NP-MRD ID

NP0310621

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

Description

Aurovertin B belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. Each ATP synthase complex has three beta subunits, and aurovertins are believed to bind with varying affinity to two subunits on sites in a cleft between the nucleotide-binding and C-terminal domains, thus preventing closure of the catalytic interfaces necessary for the cyclic interconversion of catalytic sites. It is known for its ability to inhibit oxidative phosphorylation. Aurovertin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Aurovertin B is a potentially toxic compound. Aurovertin B is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. F1F0-ATP synthase is responsible for the terminal step of oxidative phosphorylation. They do this by inhibiting the proton-pumping F1F0-ATP synthase by binding to beta-subunits in its F1 catalytic sector. 7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate is found in Calcarisporium arbuscula. Aurovertins are a mixed, noncompetitive inhibitors of both ATP hydrolysis and synthesis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212482D          

 33 35  0  0  0  0            999 V2000
    1.1313   -2.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9528   -2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897    0.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9892   -0.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070   -1.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -2.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5777   -3.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8280   -3.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6339   -4.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8842   -4.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6901   -5.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3848   -6.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5789   -6.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0233   -6.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -5.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7463   -6.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9966   -6.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2457   -4.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    0.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694   -0.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    0.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    0.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414    0.3436    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
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
  8 27  1  0  0  0  0
  6 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -7.4049   -1.0202   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3056   -1.8591   -1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -1.2367   -1.0132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8708   -0.0654   -1.7658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    0.6387   -1.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6545    2.0168   -1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152   -0.1031   -1.4078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4922    0.8704   -1.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -1.2324   -0.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9262   -1.0034    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2022   -0.9506   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -0.7233    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.6712   -0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -0.4474    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9976   -0.3949   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2410   -0.1687    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2826   -0.0170    1.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392    0.1887    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4236    0.3272    3.2944 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6419    0.2549    1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6370    0.0997    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8057    0.1532   -0.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0728    0.3646   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4144   -0.1121   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3576   -0.2845   -2.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.5448    0.4491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3937   -0.9589    0.3406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2693   -1.2941    1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1345    0.5550    0.2615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1214    1.3267    0.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0543    2.2507    1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861    3.0543    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    2.3887    2.2937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2990   -1.1359   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1966    0.0705   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8037   -1.3612    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2223   -2.8431   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5026   -2.1366   -2.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858   -1.9697   -1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    2.7738   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5499    2.3640   -2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127    2.0876   -2.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5269   -0.4013   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4497    1.2407   -0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0545   -2.1403   -1.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8898   -0.8754    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.0765   -1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4932   -0.5959    1.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5786   -0.7964   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740   -0.3216    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247   -0.5256   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5696    0.4271    1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9926    1.1043    0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4753   -0.6132    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7777    0.7338   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5501    0.3168   -2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2191   -1.3534   -2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3018    0.0724   -2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143   -1.3755    2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9716   -0.4497    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7641   -2.2565    1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    0.7869    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0828    4.0732    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2410    3.1043    3.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1655    2.6711    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 27  1  0
 27 28  1  1
 27 26  1  0
 26  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 24  2  0
 24 25  1  0
 24 21  1  0
 21 22  1  0
 22 23  1  0
 21 20  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
  9  7  1  0
  7  8  1  0
 27  3  1  0
 17 16  1  0
  7  5  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  6
  6 40  1  0
  6 41  1  0
  6 42  1  0
 29 62  1  1
 32 63  1  0
 32 64  1  0
 32 65  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
  9 45  1  6
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 20 52  1  0
  7 43  1  6
  8 44  1  0
M  END


  Mrv0541 02241212482D          

 33 35  0  0  0  0            999 V2000
    1.1313   -2.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9528   -2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897    0.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9892   -0.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070   -1.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -2.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5777   -3.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8280   -3.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6339   -4.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8842   -4.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6901   -5.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3848   -6.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5789   -6.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0233   -6.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -5.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7463   -6.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9966   -6.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2457   -4.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    0.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694   -0.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    0.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    0.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414    0.3436    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
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
  8 27  1  0  0  0  0
  6 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC2(C)C(OC(C)=O)C1(C)OC(C=CC=CC=CC1=C(C)C(OC)=CC(=O)O1)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3

> <INCHI_KEY>
QXCOFYWOWZJFEA-UHFFFAOYSA-N

> <FORMULA>
C25H32O8

> <MOLECULAR_WEIGHT>
460.5168

> <EXACT_MASS>
460.209718

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
50.315505038682275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-ethyl-4-hydroxy-3-[6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
2.5531159653333333

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.9124340730191

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7119013364614455

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000001

> <JCHEM_REFRACTIVITY>
125.5026

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.112  -5.548   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.779  -3.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.979  -1.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.167   0.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.223  -3.066   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.008  -1.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.713  -1.011   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.053  -3.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -4.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.041  -5.484   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.545  -5.813   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.012  -7.281   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.517  -7.610   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.984  -9.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.488  -9.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.955 -10.873   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.918 -12.012   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.414 -11.683   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.377 -12.821   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.947 -10.215   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      14.460 -11.202   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.927 -12.670   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.525  -8.268   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.498   0.035   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.503  -1.704   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.320   1.730   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.866   1.567   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.492   0.161   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.771   2.813   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.944   0.641   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   10   33                                             
CONECT    5    4    6   29                                                  
CONECT    6    5    7    8   28                                             
CONECT    7    6    3                                                       
CONECT    8    6    9   27                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17                                                       
CONECT   24   19   25                                                       
CONECT   25   24                                                            
CONECT   26   18                                                            
CONECT   27    8                                                            
CONECT   28    6                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₈

Average Mass

460.5168 Da

Monoisotopic Mass

460.20972 Da

IUPAC Name

7-ethyl-4-hydroxy-3-[6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

Traditional Name

7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

CAS Registry Number

Not Available

SMILES

CCC1OC2(C)C(OC(C)=O)C1(C)OC(C=CC=CC=CC1=C(C)C(OC)=CC(=O)O1)C2O

InChI Identifier

InChI=1S/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3

InChI Key

QXCOFYWOWZJFEA-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
Calcarisporium arbuscula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
1,4-dioxepane
Alkyl aryl ether
Pyranone
Dioxepane
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Monocarboxylic acid or derivatives
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.02	ALOGPS
logP	2.55	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.5 m³·mol⁻¹	ChemAxon
Polarizability	50.32 Å³	ChemAxon
Number of Rings	3	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

2261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate (NP0310621)

MOL for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D MOL for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D SDF for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D-SDF for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

PDB for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D PDB for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

SMILES for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

INCHI for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

Structure for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)

3D Structure for NP0310621 (7-ethyl-4-hydroxy-3-[6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate)