NP-MRD: Showing NP-Card for 9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate (NP0312218)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 08:48:46 UTC

Updated at

2022-09-11 08:48:47 UTC

NP-MRD ID

NP0312218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

Description

9-(Chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate 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. 9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate is found in Serratula strangulata. Based on a literature review very few articles have been published on 9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112210482D          

 37 40  0  0  0  0            999 V2000
    1.8651    1.7897    0.0000 C   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
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494    3.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    2.5978    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8088    3.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9897    3.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6348    4.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4027    3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257    2.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2937    2.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8807    2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1127    2.7300    0.0000 C   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 C   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
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   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
    2.3265    0.4710    0.0000 C   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
    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
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    0.0000 Cl  0  0  0  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  0  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  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -1.4375   -0.3952   -3.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227   -0.6868   -2.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982   -1.0589   -2.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262   -1.0659   -3.5507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -1.4127   -1.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5476   -1.0643   -0.0998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2120   -0.7246   -0.6243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5273    0.4502   -0.0231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1486    0.3749   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501    0.1526    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019   -0.0046    1.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    0.0971    0.0854 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3416   -0.8905   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210    1.4772   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    2.6805    0.7550 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0530   -0.1339    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903   -0.1552    1.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0558   -1.1628    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5545   -1.0512    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700   -1.8175    1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5508   -1.7212    1.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3016   -0.8977    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6893   -0.8519    0.7634 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6553   -0.1386   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2640   -0.2120   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    1.7870   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4771    1.7108   -0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014    2.3271   -2.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6664    1.0450   -0.4146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5918    1.9162    0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4048    0.8944    1.1464 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7359    1.3551    2.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5374   -0.3617    1.2360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0781   -1.4188    0.5388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4256   -0.7543    2.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0602   -1.0761    3.3375 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2463    0.0306    0.6329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6915   -0.4181   -4.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -0.1264   -2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -1.9685    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5469   -1.6076   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633    0.2887    1.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081   -1.8944   -0.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -1.0855   -1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -0.5016   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    1.5126   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633    1.6532   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685    0.8578    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -0.4399    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -2.2062    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195   -0.8684   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6575   -2.4897    1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0833   -2.3109    2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3239   -1.4481    0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353    0.5225   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959    0.3941   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2864    2.3781    0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619    2.4464   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539    2.3131   -2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    2.8391   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2743    0.5490   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2359    2.4652   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0740    2.6221    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3006    0.6249    0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6067    1.8523    2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8379   -1.1577   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9459    0.0633    3.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8243   -1.6935    2.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    0.5443    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 12 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8 26  1  0
 26 27  1  0
 27 28  2  3
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  6
 33 35  1  0
 35 36  1  0
 33 37  1  0
 37  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
 25 19  1  0
  7  8  1  0
 37 29  1  0
  7  6  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
  8 42  1  1
 26 57  1  0
 26 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  6
 30 62  1  0
 30 63  1  0
 31 64  1  6
 32 65  1  0
 34 66  1  0
 35 67  1  0
 35 68  1  0
 37 69  1  1
  6 40  1  1
  1 38  1  0
  1 39  1  0
  7 41  1  6
M  END


  Mrv1652309112210482D          

 37 40  0  0  0  0            999 V2000
    1.8651    1.7897    0.0000 C   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
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494    3.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939    2.5978    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8088    3.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218    3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9897    3.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6348    4.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4027    3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257    2.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2937    2.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8807    2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1127    2.7300    0.0000 C   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 C   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
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   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
    2.3265    0.4710    0.0000 C   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
    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
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    0.0000 Cl  0  0  0  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  0  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  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCl)(OCCC1=CC=C(O)C=C1)C(=O)OC1CC(=C)C2CC(O)C(O)(CCl)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H32Cl2O8/c1-14-10-19(36-25(33)26(3,12-28)35-9-8-16-4-6-17(30)7-5-16)21-15(2)24(32)37-23(21)22-18(14)11-20(31)27(22,34)13-29/h4-7,18-23,30-31,34H,1-2,8-13H2,3H3

> <INCHI_KEY>
VLUKWHIZVPGABG-UHFFFAOYSA-N

> <FORMULA>
C27H32Cl2O8

> <MOLECULAR_WEIGHT>
555.45

> <EXACT_MASS>
554.1474234

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.00960420215898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

> <JCHEM_LOGP>
3.2446981690000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.79903321172398

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.201473380394306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2665841195282956

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000002

> <JCHEM_REFRACTIVITY>
136.13639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.435   4.864   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.001   5.426   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.639   5.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.679   7.028   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.599   4.620   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      12.122   4.849   0.000  0.00  0.00          Cl+0
HETATM   12  O   UNK     0      10.843   6.784   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.277   6.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.481   7.181   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.914   6.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.118   7.579   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.552   7.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.781   5.494   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      19.215   4.931   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.577   4.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.144   5.096   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.218  -3.132   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.634  -2.601   0.000  0.00  0.00           C+0
HETATM   37 Cl   UNK     0       5.366  -4.117   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22    4   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   29   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
9-(Chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoic acid	Generator

Chemical Formula

C₂₇H₃₂Cl₂O₈

Average Mass

555.4500 Da

Monoisotopic Mass

554.14742 Da

IUPAC Name

9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

Traditional Name

9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(CCl)(OCCC1=CC=C(O)C=C1)C(=O)OC1CC(=C)C2CC(O)C(O)(CCl)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C27H32Cl2O8/c1-14-10-19(36-25(33)26(3,12-28)35-9-8-16-4-6-17(30)7-5-16)21-15(2)24(32)37-23(21)22-18(14)11-20(31)27(22,34)13-29/h4-7,18-23,30-31,34H,1-2,8-13H2,3H3

InChI Key

VLUKWHIZVPGABG-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
Serratula strangulata	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
Guaiane sesquiterpenoid
Sesquiterpenoid
Tyrosol derivative
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Alcohol
Carbonyl group
Alkyl halide
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
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	3.24	ChemAxon
pKa (Strongest Acidic)	10.2	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.14 m³·mol⁻¹	ChemAxon
Polarizability	56.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73810079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate (NP0312218)

MOL for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

3D MOL for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

3D SDF for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

3D-SDF for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

PDB for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

3D PDB for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

SMILES for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

INCHI for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

Structure for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)

3D Structure for NP0312218 (9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate)