NP-MRD: Showing NP-Card for 7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate (NP0186445)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 02:17:52 UTC

Updated at

2022-09-04 02:17:53 UTC

NP-MRD ID

NP0186445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate

Description

7,8-Dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate 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. 7,8-Dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518032D          

 35 37  0  0  0  0            999 V2000
    1.1380    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5505    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    7.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809    1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2404    0.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    1.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430   -1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1574   -2.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8272   -1.6429    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 23 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
   10.0277   -1.5112   -2.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6460   -1.5998   -2.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7328   -1.1751   -1.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0911   -0.5618   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1059   -0.1525    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757    0.4191    1.1723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8554   -0.3374   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323   -0.9321   -1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878   -1.0926   -1.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826   -0.7418   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -0.7972   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -0.4466    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -0.4491    0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -0.1168    1.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.0928    1.9392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1109   -0.8824    1.0624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4713   -0.6951    0.9633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2425   -2.0041    0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0650    0.1081    2.1398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7970   -0.3996    3.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4294    1.4308    1.7989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0255    2.5575    2.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7226    1.5566    0.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8256    0.2943   -0.1198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1599    0.1013   -0.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9901    0.1768   -1.3666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2168   -1.1617   -2.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4183    1.1386   -2.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9421    1.3426    1.9574 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2840    2.0563    0.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022    3.1052    1.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    3.7858   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453    3.4638    2.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3730   -1.3442   -2.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925   -2.0400   -3.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5288   -2.5010   -2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3839   -1.0938   -3.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3451   -0.8792   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1312   -0.3698   -0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -1.4826   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984   -0.3596    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -1.1310   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6528   -0.1219    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -0.7363   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    0.1512    2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5983   -0.4628    3.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2353   -1.8213    0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3706   -2.4228    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128   -2.7298    0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1603    0.1456    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4243   -1.1379    3.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675    3.4106    2.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0065    2.8853    2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760    2.1497    3.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7153    0.8841   -0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326    0.3141   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3926   -1.8727   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -1.0286   -3.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.6095   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6965    1.8000   -2.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    1.7844    2.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5939    4.4409   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.3396    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5153    3.0862   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0482   -2.6172   -3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7748   -2.7546   -3.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -1.2621   -4.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 26 28  1  0
 21 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
  8 34  2  0
 34 35  1  0
 34  3  1  0
 29 15  1  0
 24 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  1
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
 26 56  1  1
 27 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  1  1
 32 62  1  0
 32 63  1  0
 32 64  1  0
 35 65  1  0
 35 66  1  0
 35 67  1  0
M  END


  Mrv1533004231518032D          

 35 37  0  0  0  0            999 V2000
    1.1380    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5505    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    7.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809    1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2404    0.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    1.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444   -0.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430   -1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1574   -2.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8272   -1.6429    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  8  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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 23 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)OC(C=CC=CC=CC2OC3(C)C(O)C(C)(OC3(O)C(C)O)C2OC(C)=O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O10/c1-14-17(33-20(28)13-19(14)31-6)11-9-7-8-10-12-18-21(32-16(3)27)23(4)22(29)24(5,34-18)25(30,35-23)15(2)26/h7-13,15,18,21-22,26,29-30H,1-6H3

> <INCHI_KEY>
KQZNWRCEZLXYOS-UHFFFAOYSA-N

> <FORMULA>
C25H32O10

> <MOLECULAR_WEIGHT>
492.521

> <EXACT_MASS>
492.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.57958611960257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.2105745866666666

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.77113004351975

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.032847842141274

> <JCHEM_PKA_STRONGEST_BASIC>
-3.498101878055797

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
128.4084

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.124  11.857   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.894  10.524   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.434  10.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.204  11.857   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.744  11.857   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.514  13.191   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.514  10.524   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.744   9.190   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.204   9.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.434   7.856   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.514   7.856   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.744   6.523   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.514   5.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.744   3.855   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.514   2.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.744   1.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.536   2.575   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.692   4.419   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.602   1.188   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.062   1.188   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.692  -2.044   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.831   0.418   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.898   3.183   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.291   1.923   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.449   0.573   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.509   3.239   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.496  -1.404   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.934  -2.837   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.894  -4.041   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.411  -3.067   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   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   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   23   17   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
7,8-Dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₂O₁₀

Average Mass

492.5210 Da

Monoisotopic Mass

492.19955 Da

IUPAC Name

7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate

Traditional Name

7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(C=CC=CC=CC2OC3(C)C(O)C(C)(OC3(O)C(C)O)C2OC(C)=O)=C1C

InChI Identifier

InChI=1S/C25H32O10/c1-14-17(33-20(28)13-19(14)31-6)11-9-7-8-10-12-18-21(32-16(3)27)23(4)22(29)24(5,34-18)25(30,35-23)15(2)26/h7-13,15,18,21-22,26,29-30H,1-6H3

InChI Key

KQZNWRCEZLXYOS-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

Not Available

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
Hemiacetal
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	2.46	ALOGPS
logP	1.21	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.41 m³·mol⁻¹	ChemAxon
Polarizability	51.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

74318592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate (NP0186445)

MOL for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

3D MOL for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

3D SDF for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

3D-SDF for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

PDB for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

3D PDB for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

SMILES for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

INCHI for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

Structure for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)

3D Structure for NP0186445 (7,8-dihydroxy-7-(1-hydroxyethyl)-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-4-yl acetate)