NP-MRD: Showing NP-Card for 3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate (NP0259784)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 01:46:00 UTC

Updated at

2022-09-08 01:46:01 UTC

NP-MRD ID

NP0259784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate

Description

3,6,7-Tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate 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. 3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate is found in Thapsia villosa. Based on a literature review very few articles have been published on 3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082203462D          

 36 38  0  0  0  0            999 V2000
    4.2920    3.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.6939    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342    1.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    2.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592    1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791    0.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0676    0.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4284   -0.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438    1.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    0.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 30 36  1  0  0  0  0
  8 36  1  0  0  0  0
 26 36  1  0  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
    7.3477   -3.5698    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -4.1978    0.0106 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8026   -2.8844   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6739   -2.5054   -0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723   -1.4354   -0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565   -0.8706   -1.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -1.0242   -0.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087    0.0131   -0.6782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4174   -0.3888   -1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.5353   -1.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3367   -1.9380   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -0.3030   -2.4609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9946   -1.0971   -3.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -0.8200   -4.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -2.0056   -3.3714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640    0.5279   -0.2281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8517    0.3607    0.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3399   -0.8676    0.5309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253   -1.3768    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0915   -2.6828    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1116   -0.6614   -0.8489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    1.3440    1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088    1.5403    1.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993    2.4614    2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357    0.6889    1.0408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3576    0.9849    1.2484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2256    2.2550    1.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1701    2.4372    2.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7476    3.0963    2.9879 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.6793    1.0244 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7355    0.6792    1.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809    2.6005    0.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766    3.4474    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2405    4.4106   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    3.4334    1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7274    1.1924    0.2755 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3060   -3.4981    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404   -2.5680    0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1922   -4.2646    0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1618   -2.4184   -1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -2.9801    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5123    0.3334   -1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673    0.6581   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502   -0.6589    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.1046    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -2.6033   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728   -2.2657   -1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4199    0.2524   -5.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062   -0.9852   -4.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.5043   -5.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489    1.4828   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5310    0.8209   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8402   -3.4557   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7394   -3.0293    1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1967   -2.5324    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8324    1.8210    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    3.4624    2.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439    2.6383    3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7267    1.9644    3.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.3254    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2896    2.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976    0.4519    1.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995   -0.1884    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078    1.1165    2.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1751    4.0345   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629    5.3420    0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624    4.6941   -1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3845    2.0317   -0.4128 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 12 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 30 32  1  6
 32 33  1  0
 33 34  1  0
 33 35  2  0
 30 36  1  0
 36  8  1  0
 25 16  1  0
 36 26  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  0
  8 42  1  6
  9 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  6
 17 52  1  6
 20 53  1  0
 20 54  1  0
 20 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  1
 31 62  1  0
 31 63  1  0
 31 64  1  0
 34 65  1  0
 34 66  1  0
 34 67  1  0
 36 68  1  6
M  END


  Mrv1652309082203462D          

 36 38  0  0  0  0            999 V2000
    4.2920    3.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.6939    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2342    1.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    2.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592    1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791    0.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0676    0.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4284   -0.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438    1.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    0.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 30 36  1  0  0  0  0
  8 36  1  0  0  0  0
 26 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC=CC(=O)OC1CC(C)(OC(C)=O)C2C(OC(C)=O)C=C(C)C2C2OC(=O)C(C)(OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O10S/c1-12-10-16(31-13(2)26)20-19(12)22-21(25(6,23(30)33-22)35-15(4)28)17(32-18(29)8-9-36-7)11-24(20,5)34-14(3)27/h8-10,16-17,19-22H,11H2,1-7H3

> <INCHI_KEY>
ULVFIWRYBBZHCE-UHFFFAOYSA-N

> <FORMULA>
C25H32O10S

> <MOLECULAR_WEIGHT>
524.58

> <EXACT_MASS>
524.171618404

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.70283062502648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate

> <JCHEM_LOGP>
1.568222231333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.331406545445375

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
127.4619

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.012   6.551   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       7.782   5.029   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       6.349   4.466   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.145   5.426   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.507   5.824   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   3.882   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.001   2.381   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.771   3.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.001   5.048   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.311   3.714   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.530   1.186   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.908   0.498   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.193   1.346   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.000  -1.040   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.378   0.109   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.514   1.829   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.029   2.238   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.642   3.729   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.068   1.157   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   25                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   36                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30    8   26                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
3,6,7-Tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoic acid	Generator
3,6,7-Tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 3-(methylsulphanyl)prop-2-enoate	Generator
3,6,7-Tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 3-(methylsulphanyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₂O₁₀S

Average Mass

524.5800 Da

Monoisotopic Mass

524.17162 Da

IUPAC Name

3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate

Traditional Name

3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CSC=CC(=O)OC1CC(C)(OC(C)=O)C2C(OC(C)=O)C=C(C)C2C2OC(=O)C(C)(OC(C)=O)C12

InChI Identifier

InChI=1S/C25H32O10S/c1-12-10-16(31-13(2)26)20-19(12)22-21(25(6,23(30)33-22)35-15(4)28)17(32-18(29)8-9-36-7)11-24(20,5)34-14(3)27/h8-10,16-17,19-22H,11H2,1-7H3

InChI Key

ULVFIWRYBBZHCE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thapsia villosa	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
Pentacarboxylic acid or derivatives
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Vinylogous thioester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Acrylic acid or derivatives
Thioenolether
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Sulfenyl compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organosulfur compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.57	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	127.46 m³·mol⁻¹	ChemAxon
Polarizability	53.7 Å³	ChemAxon
Number of Rings	3	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

73806573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate (NP0259784)

MOL for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

3D MOL for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

3D SDF for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

3D-SDF for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

PDB for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

3D PDB for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

SMILES for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

INCHI for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

Structure for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)

3D Structure for NP0259784 (3,6,7-tris(acetyloxy)-3,6,9-trimethyl-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl 3-(methylsulfanyl)prop-2-enoate)