NP-MRD: Showing NP-Card for methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0298168)

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Record Information

Version

2.0

Created at

2022-09-10 09:11:37 UTC

Updated at

2022-09-10 09:11:38 UTC

NP-MRD ID

NP0298168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-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-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Lamium amplexicaule and Phlomis rigida. Methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-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


  Mrv1533004161516492D          

 32 34  0  0  0  0            999 V2000
    4.7079    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    2.0625    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    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
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    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
    2.1154   -1.0086    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
    1.5249    1.8646    0.0000 O   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
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -1.9049    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
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 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
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.0715   -4.8990   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3163   -3.7290   -0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -3.2389   -1.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -3.8967   -2.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224   -2.0390   -1.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -1.6435   -2.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852   -0.5003   -2.6981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367    0.4246   -1.5885 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6832   -0.0508   -0.6859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7419    0.7680   -0.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9017    0.0561   -0.8053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0216    0.7475   -0.3949 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2594    0.2489   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1429    0.4012   -2.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2415    0.6025    1.1169 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2675   -0.2809    1.3795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    0.0887    1.6789 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8653    0.1831    3.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261    0.9422    1.0928 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0351    2.2970    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    0.2572   -1.0313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6501   -1.1844   -0.4967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5854   -1.4977    0.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821   -1.1142    0.3470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9699   -2.1298    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688    0.1810    1.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    1.1439    0.0341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3378    1.8686   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1637    2.0824    0.5189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415    2.9567    1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410    3.9805    2.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    2.8606    1.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9621   -5.2516   -1.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -5.6283   -0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1721   -4.6957   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -2.2488   -3.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    1.4312   -1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    1.7406   -0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    1.8191   -0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0998    0.9322   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664   -0.7575   -0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -0.1359   -2.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059    1.6152    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668   -0.8710    2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767   -0.9327    1.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -0.4380    3.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004    0.6478    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    2.8003    0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022    0.2742   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -2.3832    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8105   -0.9312   -0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432   -2.4948    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6890    0.0054    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4451    0.5714    1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1411    1.8216    0.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    2.9421   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7114    1.4366   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    4.8198    2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537    3.5664    2.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    4.4582    1.3114 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 27  1  0
 27 28  1  0
 27 26  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  1
 27 29  1  1
 29 30  1  0
 30 31  1  0
 30 32  2  0
 22  5  1  0
 19 10  1  0
 22 21  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 36  1  0
  8 37  1  6
 10 38  1  6
 12 39  1  1
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  1
 20 48  1  0
 21 49  1  6
 28 55  1  0
 28 56  1  0
 28 57  1  0
 26 53  1  0
 26 54  1  0
 24 51  1  6
 25 52  1  0
 23 50  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
M  END


  Mrv1533004161516492D          

 32 34  0  0  0  0            999 V2000
    4.7079    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    2.0625    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    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
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    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
    2.1154   -1.0086    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
    1.5249    1.8646    0.0000 O   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
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -1.9049    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
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 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
M  END
> <DATABASE_ID>
NP0298168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C2C(C)(CC(O)C12O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O13/c1-7(21)32-18(2)4-10(22)19(27)8(15(26)28-3)6-29-17(14(18)19)31-16-13(25)12(24)11(23)9(5-20)30-16/h6,9-14,16-17,20,22-25,27H,4-5H2,1-3H3

> <INCHI_KEY>
HTOSOQRDFDYOGW-UHFFFAOYSA-N

> <FORMULA>
C19H28O13

> <MOLECULAR_WEIGHT>
464.42

> <EXACT_MASS>
464.152990962

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.19425255218478

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-3.81939457

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.578924620445477

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.0146792869072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760235192

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
99.12369999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.949  -1.883   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.989  -1.246   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.989  -2.786   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.322  -3.556   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.655  -3.556   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   27                                                  
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   27                                                  
CONECT   22   21   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    5   21   28                                             
CONECT   28   27                                                            
CONECT   29   22   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-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

C₁₉H₂₈O₁₃

Average Mass

464.4200 Da

Monoisotopic Mass

464.15299 Da

IUPAC Name

methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-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-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,5H,6H,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)(CC(O)C12O)OC(C)=O

InChI Identifier

InChI=1S/C19H28O13/c1-7(21)32-18(2)4-10(22)19(27)8(15(26)28-3)6-29-17(14(18)19)31-16-13(25)12(24)11(23)9(5-20)30-16/h6,9-14,16-17,20,22-25,27H,4-5H2,1-3H3

InChI Key

HTOSOQRDFDYOGW-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
Lamium amplexicaule	LOTUS Database	35616633
Phlomis rigida	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
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
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	-1.6	ALOGPS
logP	-3.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.12 m³·mol⁻¹	ChemAxon
Polarizability	44.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

124222270

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-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0298168)

MOL for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0298168 (methyl 7-(acetyloxy)-4a,5-dihydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)