NP-MRD: Showing NP-Card for methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0203213)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 22:36:55 UTC

Updated at

2022-09-04 22:36:55 UTC

NP-MRD ID

NP0203213

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Methyl 7-methyl-6-{7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate 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. methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Asperula maximowiczii. Methyl 7-methyl-6-{7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121513352D          

 40 44  0  0  0  0            999 V2000
   -0.3230    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    4.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    5.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    5.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3895    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    5.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    6.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    8.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    8.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4520    7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    8.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    6.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6895    6.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4520    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    5.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    3.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165    3.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970    3.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 30 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
   -0.1487   -6.5808   -0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3920   -5.3110   -0.5084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -4.3851    0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -4.7202    1.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -3.0650    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4655   -2.7819   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -1.5356   -1.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -0.8099   -0.0396 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9792    0.4303   -0.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455    0.5374   -0.1762 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9625    0.7162   -1.4044 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    2.0207   -1.6682 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8871    2.0454   -3.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2707    3.3147   -3.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667    2.5745   -0.7611 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2611    3.9583   -0.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070    1.9324    0.6001 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8607    0.6975    0.5423 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7187    1.6358    0.7675 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5302    1.2993    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.7631    1.0845 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9983   -2.1132    1.4220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3659   -1.8926    2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395   -0.3875    1.9085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9911   -0.2469    1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8962    0.4694    2.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984    0.9853    3.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139    0.6295    2.0473 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0521   -0.6908    1.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452   -0.3404    2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7790    0.9471    1.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6972    1.5429    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0439    1.6337    0.6344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4515    0.9831   -0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1212    1.9822   -1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2266    0.3774   -1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573    0.7760   -0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5560    1.4488    0.7930 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3113    0.0614    0.8359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3444   -0.1502   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2651   -7.1068    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791   -7.2000   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2753   -6.5647   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -3.4916   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757   -1.4129    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655   -0.4271    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4179    2.6885   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383    1.6269   -3.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    1.3619   -3.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6665    4.0127   -3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3980    2.3149   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917    4.1935    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5805    2.5731    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3941    0.5188    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    2.5793    0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510    1.8613    2.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0507   -0.3419    1.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868   -2.5659    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259   -2.2159    3.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -2.4375    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584    0.1219    2.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    1.1904    2.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342   -1.2517    2.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8284   -1.2584    1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2490    2.7308    0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1855    0.1662   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9103    1.7642   -2.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8522    3.0197   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2436    1.9229   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0995    0.7313   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3024   -0.7435   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3872    1.4495   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524   -0.1331   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    2.4198    0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5641    1.1391    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052    0.0437   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660    0.6226   -0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -1.1270   -0.5651 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 39  1  0
 39 40  1  0
 39 24  1  0
 24 23  1  0
 23 22  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 22  5  1  0
 38 28  1  0
 19 10  1  0
 22 21  1  0
 38 33  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  8 45  1  1
 10 46  1  1
 12 47  1  6
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  6
 16 52  1  0
 17 53  1  1
 18 54  1  0
 19 55  1  6
 20 56  1  0
 21 57  1  1
 39 75  1  1
 40 76  1  0
 40 77  1  0
 40 78  1  0
 24 61  1  1
 23 59  1  0
 23 60  1  0
 22 58  1  1
 28 62  1  1
 29 63  1  0
 29 64  1  0
 33 65  1  6
 34 66  1  1
 35 67  1  0
 35 68  1  0
 35 69  1  0
 36 70  1  0
 36 71  1  0
 37 72  1  0
 37 73  1  0
 38 74  1  1
M  END


  Mrv0541 04121513352D          

 40 44  0  0  0  0            999 V2000
   -0.3230    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    4.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    5.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    5.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3895    5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    5.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    6.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2145    8.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    8.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4520    7.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    8.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    6.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6895    6.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4520    5.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645    5.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    3.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165    3.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8970    3.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 30 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C2C(C)C(CC12)OC(=O)C1COC(=O)C2C(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O13/c1-10-4-5-12-14(8-36-25(34)18(10)12)24(33)38-16-6-13-15(23(32)35-3)9-37-26(19(13)11(16)2)40-27-22(31)21(30)20(29)17(7-28)39-27/h9-14,16-22,26-31H,4-8H2,1-3H3

> <INCHI_KEY>
BQMYRPGSJXGSKG-UHFFFAOYSA-N

> <FORMULA>
C27H38O13

> <MOLECULAR_WEIGHT>
570.588

> <EXACT_MASS>
570.231241284

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
58.339959857387534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 7-methyl-6-{7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-0.10203516233333368

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198724991401786

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207031709660537

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601512576

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
131.44769999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3H-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -0.603   8.530   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.937   8.530   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.707   9.863   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.937  11.197   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.247   9.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.017  11.197   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.557  11.197   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.327   9.863   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.867   9.863   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.637  11.197   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.867  12.531   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.637  13.865   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.867  15.198   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.637  16.532   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.177  13.865   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.947  15.198   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.947  12.531   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.487  12.531   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.177  11.197   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.947   9.863   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.557   8.530   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.033   7.065   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.497   6.589   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.541   7.065   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.017   8.530   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   21                                                  
CONECT   27   24   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   30   35                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7-methyl-6-{7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₈O₁₃

Average Mass

570.5880 Da

Monoisotopic Mass

570.23124 Da

IUPAC Name

methyl 7-methyl-6-{7-methyl-1-oxo-octahydrocyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3H-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C2C(C)C(CC12)OC(=O)C1COC(=O)C2C(C)CCC12

InChI Identifier

InChI=1S/C27H38O13/c1-10-4-5-12-14(8-36-25(34)18(10)12)24(33)38-16-6-13-15(23(32)35-3)9-37-26(19(13)11(16)2)40-27-22(31)21(30)20(29)17(7-28)39-27/h9-14,16-22,26-31H,4-8H2,1-3H3

InChI Key

BQMYRPGSJXGSKG-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
Asperula maximowiczii	LOTUS Database	35616633

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
Terpene lactone
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Monoterpenoid
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Monosaccharide
Oxane
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Primary 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	0	ALOGPS
logP	-0.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.45 m³·mol⁻¹	ChemAxon
Polarizability	58.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73113959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0203213)

MOL for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0203213 (methyl 7-methyl-6-{7-methyl-1-oxo-hexahydro-3h-cyclopenta[c]pyran-4-carbonyloxy}-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)