NP-MRD: Showing NP-Card for (1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate (NP0308385)

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Record Information

Version

2.0

Created at

2022-09-11 02:07:30 UTC

Updated at

2022-09-11 02:07:30 UTC

NP-MRD ID

NP0308385

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

Description

6-O-(4-methoxybenzoyl)ajugol belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review very few articles have been published on 6-o-(4-methoxybenzoyl)ajugol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204072D          

 34 37  0  0  1  0            999 V2000
   -0.3909   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -5.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4243    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 31  1  1  0  0  0
 15 32  1  0  0  0  0
 10 32  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   10.1930    1.1200   -1.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4901    0.5277   -0.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0947    0.5932   -0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190    1.2006   -1.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231    1.2559   -1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2949    0.6923   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    0.7655   -0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.3265   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.2299    0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6506    0.2917    0.1795 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9930    1.0043    1.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4848    0.7241    0.9914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9398    1.5425   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    0.9539    2.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -0.7609    0.7123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5727   -1.1605   -0.1203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6499   -1.4087    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.6539    0.4513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1969    0.0218    1.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2160    0.9047    1.1802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3786    1.9340    2.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3582    2.8684    1.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4553    0.1055    0.9116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4736    0.9374    0.4501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1702   -0.9024   -0.1626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1905   -1.8448   -0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891   -1.6278    0.0888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5143   -2.3418   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -2.2967   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -2.2096   -1.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993   -1.6088   -1.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -1.0345    0.1434 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9899    0.0796    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3709    0.0231    0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2748    0.9042   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7991    0.6886   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9655    2.2045   -1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0080    1.6433   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751    1.7625   -2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    0.8396   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    2.0893    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690    0.5528    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4102    2.5381   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038    1.7663   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259    1.1517   -1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0562    1.8565    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -1.2719    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9360   -0.3706   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340    0.0406   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8802    1.3558    0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5165    1.4258    3.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    2.4981    2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3867    2.9473    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7461   -0.4391    1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3467    0.5010    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1007   -0.4251   -1.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5205   -1.9765    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9920   -2.3809    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459   -3.1138   -0.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -2.6045   -2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8150   -1.5149   -1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -1.8026    0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744   -0.3806    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9110   -0.4668    1.0942 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
  6 33  1  0
 33 34  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 12 15  1  0
 15 32  1  0
 32 31  1  0
 31 30  2  0
 30 29  1  0
 29 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 34  3  1  0
 32 10  1  0
 27 18  1  0
 16 15  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
 33 63  1  0
 34 64  1  0
 10 40  1  6
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  1
 32 62  1  1
 31 61  1  0
 30 60  1  0
 16 48  1  6
 18 49  1  6
 20 50  1  6
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  1
 24 55  1  0
 25 56  1  6
 26 57  1  0
 27 58  1  1
 28 59  1  0
M  END


  Mrv1652309112204072D          

 34 37  0  0  1  0            999 V2000
   -0.3909   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -5.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4243    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 31  1  1  0  0  0
 15 32  1  0  0  0  0
 10 32  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308385

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(=O)O[C@@H]1C[C@](C)(O)[C@@H]2[C@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O11/c1-23(29)9-14(32-20(28)11-3-5-12(30-2)6-4-11)13-7-8-31-21(16(13)23)34-22-19(27)18(26)17(25)15(10-24)33-22/h3-8,13-19,21-22,24-27,29H,9-10H2,1-2H3/t13-,14+,15+,16+,17+,18-,19+,21-,22-,23-/m0/s1

> <INCHI_KEY>
TYZRNRJFBKBHEC-ANWGMTKTSA-N

> <FORMULA>
C23H30O11

> <MOLECULAR_WEIGHT>
482.482

> <EXACT_MASS>
482.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.67827000315067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

> <JCHEM_LOGP>
-0.5186739513333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.180580794393563

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204921721371836

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601928057

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
114.34600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.730 -11.336   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.760 -10.192   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.792   0.713   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.752   1.350   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.258   7.167   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   32                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   15   10                                                  
CONECT   33    6   34                                                       
CONECT   34   33    3                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₁₁

Average Mass

482.4820 Da

Monoisotopic Mass

482.17881 Da

IUPAC Name

(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

Traditional Name

(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C(=O)O[C@@H]1C[C@](C)(O)[C@@H]2[C@H]1C=CO[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H30O11/c1-23(29)9-14(32-20(28)11-3-5-12(30-2)6-4-11)13-7-8-31-21(16(13)23)34-22-19(27)18(26)17(25)15(10-24)33-22/h3-8,13-19,21-22,24-27,29H,9-10H2,1-2H3/t13-,14+,15+,16+,17+,18-,19+,21-,22-,23-/m0/s1

InChI Key

TYZRNRJFBKBHEC-ANWGMTKTSA-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 iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
O-glycosyl compound
P-methoxybenzoic acid or derivatives
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Aromatic monoterpenoid
Benzoate ester
Bicyclic monoterpenoid
Benzoic acid or derivatives
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
Benzoyl
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organic oxide
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	-0.52	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.35 m³·mol⁻¹	ChemAxon
Polarizability	48.68 Å³	ChemAxon
Number of Rings	4	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

9652032

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11477204

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate (NP0308385)

MOL for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

3D MOL for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

3D SDF for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

3D-SDF for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

PDB for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

3D PDB for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

SMILES for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

INCHI for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

Structure for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)

3D Structure for NP0308385 ((1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate)