NP-MRD: Showing NP-Card for methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0157869)

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Record Information

Version

2.0

Created at

2022-09-02 15:21:29 UTC

Updated at

2022-09-02 15:21:30 UTC

NP-MRD ID

NP0157869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-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 (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Gentiana verna. Based on a literature review very few articles have been published on methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217212D          

 39 42  0  0  1  0            999 V2000
    2.5645    3.3000    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  1  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  2  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  2  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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  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  2  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  1  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
    3.2789   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  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
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  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  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  1  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  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
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   -2.3414   -3.3438   -3.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1312   -1.6539    0.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0040   -0.2646    0.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2682    0.1827   -0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    0.7557    0.9211 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1624    2.1094    0.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    2.7965    1.7494 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1149    4.1609    1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    4.8945    0.6267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623    5.3000    1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1945    4.9847    2.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1394    2.8148    3.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5504   -6.0304   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3106   -3.8159   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508    0.5105   -0.4961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3422    0.0190   -1.8897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8006    0.4215   -2.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3885   -0.0683   -0.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6554    0.4578   -0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    0.4552    0.2598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7426    1.8663    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.4409   -6.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117   -2.5347   -5.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -2.9940   -5.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -3.2424   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -0.0133    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.7220    1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604    2.9066    2.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8854    3.9701    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699    4.7228    2.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0899    6.0070    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7385    0.6122   -2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    1.5309   -2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945   -0.0104   -2.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3760   -1.1619   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8502    2.0009    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    2.0835    1.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
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 39 70  1  0
 39 71  1  0
 36 66  1  6
 37 67  1  0
 35 64  1  0
 35 65  1  0
 34 63  1  6
M  END


  Mrv1652309022217212D          

 39 42  0  0  1  0            999 V2000
    2.5645    3.3000    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  1  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  2  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  2  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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  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
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  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  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  1  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  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0157869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2OC(=O)C2=CC=CC(O)=C2)[C@@H]2[C@@H](C)[C@@H](O)C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O13/c1-11-17(29)8-15-16(24(33)34-3)9-36-25(19(11)15)39-26-22(38-23(32)13-5-4-6-14(28)7-13)21(31)20(30)18(37-26)10-35-12(2)27/h4-7,9,11,15,17-22,25-26,28-31H,8,10H2,1-3H3/t11-,15+,17-,18+,19+,20+,21-,22+,25-,26-/m0/s1

> <INCHI_KEY>
QZOWXVWZQQHCEK-ITKBBIFCSA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.04749436770963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.7957144729999996

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.697630498292476

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.136458216151155

> <JCHEM_PKA_STRONGEST_BASIC>
-2.834046310100052

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
128.4288

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.787   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       7.454   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  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.122   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.121  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.454  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.787  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.453 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.120  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.120  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.786  -6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.453  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.846  -1.941   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   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26                                                       
CONECT   33    8   34   38                                                  
CONECT   34   33    5   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   33   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,4as,6S,7R,7as)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂O₁₃

Average Mass

552.5290 Da

Monoisotopic Mass

552.18429 Da

IUPAC Name

methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl (1S,4aS,6S,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2OC(=O)C2=CC=CC(O)=C2)[C@@H]2[C@@H](C)[C@@H](O)C[C@H]12

InChI Identifier

InChI=1S/C26H32O13/c1-11-17(29)8-15-16(24(33)34-3)9-36-25(19(11)15)39-26-22(38-23(32)13-5-4-6-14(28)7-13)21(31)20(30)18(37-26)10-35-12(2)27/h4-7,9,11,15,17-22,25-26,28-31H,8,10H2,1-3H3/t11-,15+,17-,18+,19+,20+,21-,22+,25-,26-/m0/s1

InChI Key

QZOWXVWZQQHCEK-ITKBBIFCSA-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
Gentiana verna	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
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
M-hydroxybenzoic acid ester
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Cyclic alcohol
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
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	0.7	ALOGPS
logP	0.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-2.8	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	10	ChemAxon
Refractivity	128.43 m³·mol⁻¹	ChemAxon
Polarizability	54.05 Å³	ChemAxon
Number of Rings	4	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

162908312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0157869)

MOL for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0157869 (methyl (1s,4as,6s,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-4,5-dihydroxy-3-(3-hydroxybenzoyloxy)oxan-2-yl]oxy}-6-hydroxy-7-methyl-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)