NP-MRD: Showing NP-Card for (+)-Acetylgaertneroside (NP0079758)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 00:48:43 UTC

Updated at

2022-04-29 00:48:43 UTC

NP-MRD ID

NP0079758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Acetylgaertneroside

Description

Methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-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. (+)-Acetylgaertneroside is found in Morinda morindoides. Based on a literature review very few articles have been published on methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202482D          

 42 46  0  0  1  0            999 V2000
    5.2132    1.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    1.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4091    0.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.4668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0853    1.1180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3960    1.8823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8894    2.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001    3.2977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6935    3.9489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0041    4.7132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8214    4.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3279    4.1751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0173    3.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5238    2.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451    4.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320    5.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976    5.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082    6.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3017    6.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123    7.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845    6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    0.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3365    0.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336    0.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898    1.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    2.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    1.6620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    1.1810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8137    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2494   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360   -1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -0.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528   -1.7294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    1.8816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9156   -0.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050   -0.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  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
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  6  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 22 29  1  6  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
 30 38  1  1  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -0.1520    7.6717    1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2715    6.3095    1.4738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182    5.2684    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    5.6267    0.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    3.8840    1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790    3.6210    1.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137    2.3386    1.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    1.2256    1.0561 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9585    1.1314   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0516   -0.5586 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0710    0.5828   -0.9413 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9806   -0.4107   -0.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3649    0.1546   -0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3915   -0.7549   -0.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655   -1.3461    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7079   -2.3144    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8270   -1.1149    1.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -1.6398   -1.5299 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4732   -1.5435   -2.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3488   -2.0076   -1.7010 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1949   -2.6359   -2.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -0.8291   -1.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1234   -1.3203   -1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    1.5510    1.5842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1048    2.8263    0.9045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4124    2.9152    1.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7946    1.7060    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7294    0.6869    1.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1715    0.2125    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -1.0700    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9860   -1.9366   -0.8470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9246   -1.3660   -2.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -2.4275   -0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755   -2.1016    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3434   -2.6127    0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9297   -3.4605   -0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2086   -3.9717    0.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1685   -3.7648   -1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9072   -3.2783   -1.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -1.4840    1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -2.6674    2.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7632   -0.4050    2.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    8.3303    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197    7.7519    0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4505    8.0110    2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410    4.4889    1.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2185    0.3754    1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -0.5019    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -0.7221    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315    0.6270   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    0.9962   -0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5711   -1.7033    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4718   -3.0261    1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9407   -2.8202   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727   -2.4850   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5876   -2.4726   -3.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.7719   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7050   -3.5055   -2.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -0.2723   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217   -2.0188   -2.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717    1.8605    2.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    2.6311   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    3.8180    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847    1.4230    2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2594    0.7831   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -2.8698   -0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5818   -0.6375   -2.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450   -1.4178    1.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8983   -2.3332    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2743   -4.8505    0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5972   -4.4299   -2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520   -3.5589   -2.4289 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
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 42  1  1
 42 40  1  0
 40 41  2  0
 40 30  1  0
 30 29  2  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 25  5  1  0
 29 28  1  0
 39 33  1  0
 22 10  1  0
 28 24  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  6 46  1  0
  8 47  1  1
 10 48  1  1
 12 49  1  1
 13 50  1  0
 13 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 18 55  1  1
 19 56  1  0
 20 57  1  1
 21 58  1  0
 22 59  1  6
 23 60  1  0
 24 61  1  1
 25 62  1  6
 26 63  1  0
 27 64  1  0
 29 65  1  0
 31 66  1  6
 32 67  1  0
 34 68  1  0
 35 69  1  0
 37 70  1  0
 38 71  1  0
 39 72  1  0
M  END


  Mrv1652304292202482D          

 42 46  0  0  1  0            999 V2000
    5.2132    1.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    1.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4091    0.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.4668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0853    1.1180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3960    1.8823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8894    2.5335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001    3.2977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6935    3.9489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0041    4.7132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8214    4.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3279    4.1751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0173    3.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5238    2.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451    4.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320    5.5906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976    5.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082    6.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3017    6.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123    7.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845    6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    0.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3365    0.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1291   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336    0.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898    1.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    2.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    1.6620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    1.1810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8137    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2494   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606   -0.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360   -1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -0.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3528   -1.7294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    1.8816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9156   -0.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050   -0.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  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
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  6  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 22 29  1  6  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
 30 38  1  1  0  0  0
  3 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079758

> <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]2O)[C@H]2[C@H]1C=C[C@]21OC(=O)C(=C1)[C@H](O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O14/c1-12(29)38-11-18-21(32)22(33)23(34)27(40-18)41-26-19-15(17(10-39-26)24(35)37-2)7-8-28(19)9-16(25(36)42-28)20(31)13-3-5-14(30)6-4-13/h3-10,15,18-23,26-27,30-34H,11H2,1-2H3/t15-,18+,19+,20+,21-,22-,23+,26+,27-,28+/m0/s1

> <INCHI_KEY>
BDUPWFOFVQZENO-PTKUQAIJSA-N

> <FORMULA>
C28H30O14

> <MOLECULAR_WEIGHT>
590.534

> <EXACT_MASS>
590.163555646

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.04171850355948

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
-0.13151235666666652

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.196189535251689

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.466863189389295

> <JCHEM_PKA_STRONGEST_BASIC>
-3.415750890187816

> <JCHEM_POLAR_SURFACE_AREA>
207.73999999999995

> <JCHEM_REFRACTIVITY>
138.0273

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       9.731   3.725   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.677   2.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.097   1.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.571   0.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.626   2.087   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.206   3.514   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.260   4.729   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.840   6.156   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.895   7.371   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.474   8.798   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.000   9.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.945   7.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.366   6.367   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.311   5.151   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      11.471   8.005   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.580  10.436   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.529  10.013   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.109  11.440   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.163  12.656   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.743  14.082   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.638  12.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.178   1.563   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.228   0.024   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.708  -0.403   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.729   1.040   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.784   2.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.648   3.530   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.124   4.978   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.127   3.102   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.245   2.205   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.519   0.846   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.332  -0.461   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.606  -1.820   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.067  -1.870   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.746  -0.562   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.020   0.796   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.659  -3.228   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.431   3.512   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.043  -0.133   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.463  -1.560   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      12.568   0.078   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      13.514  -1.137   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5   23   25   29                                             
CONECT   23   22   24                                                       
CONECT   24   23    4                                                       
CONECT   25   22   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30   26   31   38                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38   30                                                            
CONECT   39    3   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4ar,7R,7as)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₀O₁₄

Average Mass

590.5340 Da

Monoisotopic Mass

590.16356 Da

IUPAC Name

methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

Traditional Name

methyl (1R,4aR,7R,7aS)-1-{[(2S,3R,4S,5R,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(R)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-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]2O)[C@H]2[C@H]1C=C[C@]21OC(=O)C(=C1)[C@H](O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C28H30O14/c1-12(29)38-11-18-21(32)22(33)23(34)27(40-18)41-26-19-15(17(10-39-26)24(35)37-2)7-8-28(19)9-16(25(36)42-28)20(31)13-3-5-14(30)6-4-13/h3-10,15,18-23,26-27,30-34H,11H2,1-2H3/t15-,18+,19+,20+,21-,22-,23+,26+,27-,28+/m0/s1

InChI Key

BDUPWFOFVQZENO-PTKUQAIJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Morinda morindoides	Plant	KNApSAcK

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
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
2-furanone
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Carbonyl group
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	0.57	ALOGPS
logP	-0.13	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	207.74 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	138.03 m³·mol⁻¹	ChemAxon
Polarizability	56.04 Å³	ChemAxon
Number of Rings	5	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

163063486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Acetylgaertneroside (NP0079758)

MOL for NP0079758 ((+)-Acetylgaertneroside)

3D MOL for NP0079758 ((+)-Acetylgaertneroside)

3D SDF for NP0079758 ((+)-Acetylgaertneroside)

3D-SDF for NP0079758 ((+)-Acetylgaertneroside)

PDB for NP0079758 ((+)-Acetylgaertneroside)

3D PDB for NP0079758 ((+)-Acetylgaertneroside)

SMILES for NP0079758 ((+)-Acetylgaertneroside)

INCHI for NP0079758 ((+)-Acetylgaertneroside)

Structure for NP0079758 ((+)-Acetylgaertneroside)

3D Structure for NP0079758 ((+)-Acetylgaertneroside)