NP-MRD: Showing NP-Card for (3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate (NP0150068)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 06:04:52 UTC

Updated at

2022-09-02 06:04:52 UTC

NP-MRD ID

NP0150068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate

Description

(3AR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2R,3S)-2-hydroxy-3-methylpentanoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate is found in Ixeris japonica and Ixeris stolonifera. Based on a literature review very few articles have been published on (3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2R,3S)-2-hydroxy-3-methylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208052D          

 38 41  0  0  1  0            999 V2000
   -1.7577    3.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    2.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7433    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    2.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6856    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4001    2.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1271    0.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    0.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -0.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    0.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278    1.3739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2292    2.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0361    2.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6492    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    3.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    3.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    4.3714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5513    4.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5513    5.6089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2658    6.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9803    5.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    6.0214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8368    6.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    5.6089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4079    6.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    4.7839    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4079    4.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    3.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    2.8563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
 24 37  1  0  0  0  0
 38 37  1  1  0  0  0
  2 38  1  0  0  0  0
 21 38  1  0  0  0  0
M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
   -0.7994    3.1532   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    1.8480   -0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    1.1446   -1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118   -0.0379   -0.3806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7454   -0.3032   -0.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8091   -0.1490    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    0.2498    1.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2205   -0.4266   -0.1997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3741   -0.8524   -1.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0833    0.7593    0.0800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7103    1.8540   -0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5424    0.4249   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0076   -0.6669    0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5282   -1.2239   -0.4671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5325   -1.9744   -1.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -2.1613   -2.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1606   -2.5492   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -3.3963   -2.6282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -1.9700   -0.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -0.7621   -0.4605 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1962   -0.1106    0.8344 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5560   -0.3081    1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -1.4303    2.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797    0.6390    0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289    0.8189    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368   -0.0979    1.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9430    0.4750    1.5153 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0191   -0.3863    1.2772 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1858    0.1373    2.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238   -0.6501    1.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3290   -0.2887   -0.2015 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7937   -1.5174   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1108    0.1583   -0.9857 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0226    1.5347   -1.0610 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -0.4797   -0.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0422   -1.8622   -0.5071 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6288    1.5583    0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2100    1.3939    0.6154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4741    3.6607   -1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940    3.7747   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088    1.8100   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.8370   -2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    0.3112    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5352   -1.2861    0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0612   -1.7908   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9866    1.1149    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7700    2.8447   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4457    1.9010   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7159    1.6865   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1945    1.3057    0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7212    0.0806   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5983   -1.6579    0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8074   -0.3977    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1100   -0.7355    0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.9129    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -1.7145   -2.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -2.7602   -3.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   -0.0812   -1.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -0.2965    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570   -1.0838    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -1.9257    2.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -2.2266    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5731   -1.0000    1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -1.4168    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8938    0.1547    3.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    1.1957    1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0992   -1.4706    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1055    0.4936   -0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0584   -1.4891   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551   -0.2384   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4507    1.9137   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9784   -0.2016   -0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -2.3087    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791    2.6056    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241    1.1615   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1465    1.9124    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 38  1  0
 38 37  1  0
 37 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  2  3
 15 14  1  0
 14  4  1  0
 21 38  1  0
 14 20  1  0
 35 26  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 12 50  1  0
 12 51  1  0
 10 46  1  1
 11 47  1  0
 11 48  1  0
 11 49  1  0
  8 44  1  1
  9 45  1  0
  4 43  1  1
  3 41  1  0
  3 42  1  0
  1 39  1  0
  1 40  1  0
 38 76  1  1
 37 74  1  0
 37 75  1  0
 26 63  1  1
 28 64  1  1
 29 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  1
 32 69  1  0
 33 70  1  6
 34 71  1  0
 35 72  1  6
 36 73  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 21 59  1  1
 20 58  1  6
 16 56  1  0
 16 57  1  0
 14 55  1  1
M  END


  Mrv1652309022208052D          

 38 41  0  0  1  0            999 V2000
   -1.7577    3.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    2.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7433    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    2.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6856    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4001    2.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1271    0.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525   -0.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    0.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -0.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    0.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9278    1.3739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2292    2.1419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0361    2.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6492    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    3.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    3.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    4.3714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5513    4.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5513    5.6089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2658    6.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9803    5.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8368    6.0214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8368    6.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    5.6089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4079    6.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224    4.7839    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4079    4.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    3.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    2.8563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
 24 37  1  0  0  0  0
 38 37  1  1  0  0  0
  2 38  1  0  0  0  0
 21 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H](O)C(=O)O[C@@H]1CC(=C)[C@@H]2CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O11/c1-6-10(2)20(29)26(34)35-16-7-11(3)14-8-15(12(4)18(14)24-19(16)13(5)25(33)38-24)36-27-23(32)22(31)21(30)17(9-28)37-27/h10,14,16-24,27-32H,3,5-9H2,1-2,4H3/t10-,14-,16+,17+,18-,19+,20+,21+,22-,23+,24+,27+/m0/s1

> <INCHI_KEY>
UBVAFNHLMOOUAJ-YEMRPPDESA-N

> <FORMULA>
C27H38O11

> <MOLECULAR_WEIGHT>
538.59

> <EXACT_MASS>
538.241412044

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.145697297611434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2R,3S)-2-hydroxy-3-methylpentanoate

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
0.06897612100000025

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.58757186152257

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.017565650393761

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810921499768916

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
132.0184

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,6aR,9aR,9bR)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2R,3S)-2-hydroxy-3-methylpentanoate

> <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      -3.281   7.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.735   5.561   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.606   4.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.721   2.978   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.387   2.208   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.054   2.978   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.054   4.518   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.280   2.208   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.280   0.668   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.614   2.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.614   4.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.947   2.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.281   2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.994   2.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.971   0.571   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.711  -0.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.428   0.073   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.882  -1.398   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.352   1.305   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.465   2.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.028   3.998   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.534   4.318   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.679   3.288   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.695   5.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.029   6.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.029   8.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.362   8.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.362  10.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.696  11.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.030  10.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.029  11.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.029  12.780   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -7.695  10.470   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.361  11.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.695   8.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.361   8.160   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.288   6.476   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.258   5.332   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    4   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   22   38                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   24   38                                                       
CONECT   38   37    2   21                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4R,6ar,9ar,9BR)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl (2R,3S)-2-hydroxy-3-methylpentanoic acid	Generator

Chemical Formula

C₂₇H₃₈O₁₁

Average Mass

538.5900 Da

Monoisotopic Mass

538.24141 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H](O)C(=O)O[C@@H]1CC(=C)[C@@H]2CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C27H38O11/c1-6-10(2)20(29)26(34)35-16-7-11(3)14-8-15(12(4)18(14)24-19(16)13(5)25(33)38-24)36-27-23(32)22(31)21(30)17(9-28)37-27/h10,14,16-24,27-32H,3,5-9H2,1-2,4H3/t10-,14-,16+,17+,18-,19+,20+,21+,22-,23+,24+,27+/m0/s1

InChI Key

UBVAFNHLMOOUAJ-YEMRPPDESA-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
Ixeris japonica	LOTUS Database	35616633
Ixeris stolonifera A.Gray	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	0.38	ALOGPS
logS	-2.5	ALOGPS

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

163001442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate (NP0150068)

MOL for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

3D MOL for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

3D SDF for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

3D-SDF for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

PDB for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

3D PDB for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

SMILES for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

INCHI for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

Structure for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)

3D Structure for NP0150068 ((3ar,4r,6ar,9ar,9br)-9-methyl-3,6-dimethylidene-2-oxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2r,3s)-2-hydroxy-3-methylpentanoate)