NP-MRD: Showing NP-Card for 3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one (NP0146178)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:31:42 UTC

Updated at

2022-09-02 01:31:42 UTC

NP-MRD ID

NP0146178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one

Description

Artemoin B belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. An artemoin in which the two hydroxy groups on the C-30 side-chain are located at positions 17 and 18. Artemoin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Artemoin B has been detected, but not quantified in, fruits. 3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one is found in Annona atemoya. This could make artemoin b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307142D          

 39 39  0  0  0  0            999 V2000
   -9.5188   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   20.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8043   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0898   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6609   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9141   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7707   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6286   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7720   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4864   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3740   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6691   19.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2211   20.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9154   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0016   20.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   20.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   18.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3885   21.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8086   20.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 26  1  0  0  0  0
 31  2  1  0  0  0  0
 31 30  1  0  0  0  0
 32 27  1  0  0  0  0
 32 30  2  0  0  0  0
 33 28  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 32  1  0  0  0  0
 36 33  1  0  0  0  0
 37 34  1  0  0  0  0
 38 35  2  0  0  0  0
 39 31  1  0  0  0  0
 39 35  1  0  0  0  0
M  END

     RDKit          3D

105105  0  0  0  0  0  0  0  0999 V2000
  -11.1433    0.2416    5.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0586    0.4514    4.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2810   -0.5536    3.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1779   -0.3632    2.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4364   -1.3727    1.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3930   -1.2533    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0443   -1.5090    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9420   -1.4055    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696   -2.3701   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046   -2.4689   -2.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9196   -1.3240   -2.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2380   -0.1061   -2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8528   -0.3035   -1.9701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8869   -1.2432   -0.8899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549    0.8530   -1.5346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7125    0.4546   -1.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1992    2.1933   -2.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685    2.7053   -3.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    2.6952   -4.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3256    3.3280   -3.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885    2.7404   -2.9342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.3379   -3.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737    0.6291   -2.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616    1.3640   -2.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    0.6855   -1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506   -0.6669   -1.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811   -1.5642   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4062   -1.3141   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8337   -0.1061   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3812   -0.0934   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7369    1.1584    0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1365    1.2508    1.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5919    0.1181    2.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8343   -0.7854    3.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6620   -1.7134    4.1822 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2383   -1.6877    5.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9764   -1.2838    4.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9700   -0.1737    3.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9674    0.5192    2.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0200   -0.1917    5.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7975   -0.5320    6.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3292    1.2082    6.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2037    1.4706    4.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0385    0.3288    5.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1529   -1.5608    4.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2442   -0.4219    3.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2332   -0.6235    3.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1619    0.6490    2.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4628   -1.3133    1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3369   -2.3841    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6469   -2.0577   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4736   -0.2816    0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0141   -2.4899    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600   -0.7441    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283   -1.7034    0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9548   -0.3773   -0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3643   -3.4150   -0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1605   -2.0644   -1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2735   -3.0473   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6835   -3.2534   -2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -0.9757   -3.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4091   -1.6879   -3.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7952    0.6156   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1095    0.4865   -3.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317   -0.9298   -2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -0.7999   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921    0.9726   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7735   -0.5032   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2284    2.5611   -1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5433    2.8621   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0162    2.4027   -3.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629    3.8623   -3.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    1.6876   -4.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983    3.2336   -5.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    3.3723   -4.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    4.4352   -3.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    2.6441   -1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938    3.3730   -2.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025    0.7778   -3.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613    1.3707   -4.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    0.5170   -1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5811   -0.4139   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5691    2.3890   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772    1.3999   -3.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851    0.6865   -0.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912    1.3992   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -1.2089   -1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441   -0.6351   -2.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -1.8408   -0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816   -2.5836   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9786   -1.3983   -2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8567   -2.1985   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6402    0.8377   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4442   -0.1338    0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6520   -0.9617    0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8526   -0.1571   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2939    2.0137   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8288    1.3716    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0593    1.3552    1.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014    2.1657    2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7245   -0.8265    3.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5256   -2.7449    3.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1598   -1.7787    5.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6279   -0.7403    6.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7322   -2.5340    6.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 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
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 38 39  2  0
 38 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  5 49  1  0
  5 50  1  0
  6 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
  8 55  1  0
  8 56  1  0
  9 57  1  0
  9 58  1  0
 10 59  1  0
 10 60  1  0
 11 61  1  0
 11 62  1  0
 12 63  1  0
 12 64  1  0
 13 65  1  6
 14 66  1  0
 15 67  1  1
 16 68  1  0
 17 69  1  0
 17 70  1  0
 18 71  1  0
 18 72  1  0
 19 73  1  0
 19 74  1  0
 20 75  1  0
 20 76  1  0
 21 77  1  0
 21 78  1  0
 22 79  1  0
 22 80  1  0
 23 81  1  0
 23 82  1  0
 24 83  1  0
 24 84  1  0
 25 85  1  0
 25 86  1  0
 26 87  1  0
 26 88  1  0
 27 89  1  0
 27 90  1  0
 28 91  1  0
 28 92  1  0
 29 93  1  0
 29 94  1  0
 30 95  1  0
 30 96  1  0
 31 97  1  0
 31 98  1  0
 32 99  1  0
 32100  1  0
 34101  1  0
 35102  1  6
 36103  1  0
 36104  1  0
 36105  1  0
M  END


  Mrv0541 05061307142D          

 39 39  0  0  0  0            999 V2000
   -9.5188   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   20.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8043   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0898   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6609   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9141   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7707   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6286   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7720   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4864   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3740   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6691   19.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2211   20.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9154   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   19.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   19.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0016   20.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   20.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   18.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3885   21.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8086   20.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 26  1  0  0  0  0
 31  2  1  0  0  0  0
 31 30  1  0  0  0  0
 32 27  1  0  0  0  0
 32 30  2  0  0  0  0
 33 28  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 32  1  0  0  0  0
 36 33  1  0  0  0  0
 37 34  1  0  0  0  0
 38 35  2  0  0  0  0
 39 31  1  0  0  0  0
 39 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H66O4/c1-3-4-5-6-7-8-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-12-10-9-11-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3

> <INCHI_KEY>
NXSNZSWFXOMAOD-UHFFFAOYSA-N

> <FORMULA>
C35H66O4

> <MOLECULAR_WEIGHT>
550.8961

> <EXACT_MASS>
550.4961106

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
74.25533327526759

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(17,18-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
9.85

> <JCHEM_LOGP>
11.779610253666664

> <ALOGPS_LOGS>
-7.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.941437150411005

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.883475303328535

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440192571762076

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
166.4833

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.90e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(17,18-dihydroxytriacontyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -17.768  37.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.211  37.687   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -16.435  36.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.101  37.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.767  36.560   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.434  37.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.100  36.560   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.766  37.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.573  37.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.239  36.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.906  36.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.905  37.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.240  37.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.572  36.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.574  36.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.433  36.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.238  37.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.907  37.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.099  37.330   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.904  36.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.241  36.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.765  36.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.571  37.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.575  37.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.431  37.330   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.237  36.560   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.908  36.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.098  36.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.903  37.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.649  36.703   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.679  37.848   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.242  37.330   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.764  37.330   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.430  36.560   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.403  38.861   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.764  38.870   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.430  35.020   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      21.259  39.892   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      23.909  39.182   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   31                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   16                                                       
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   17                                                       
CONECT   15   13   18                                                       
CONECT   16    8   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   23                                                       
CONECT   21   18   24                                                       
CONECT   22   19   25                                                       
CONECT   23   20   26                                                       
CONECT   24   21   27                                                       
CONECT   25   22   28                                                       
CONECT   26   23   29                                                       
CONECT   27   24   32                                                       
CONECT   28   25   33                                                       
CONECT   29   26   34                                                       
CONECT   30   31   32                                                       
CONECT   31    2   30   39                                                  
CONECT   32   27   30   35                                                  
CONECT   33   28   34   36                                                  
CONECT   34   29   33   37                                                  
CONECT   35   32   38   39                                                  
CONECT   36   33                                                            
CONECT   37   34                                                            
CONECT   38   35                                                            
CONECT   39   31   35                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-(17,18-Dihydroxytriacontyl)-5-methyl-2(5H)-furanone	ChEBI
3-(17,18-Dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one	ChEBI

Chemical Formula

C₃₅H₆₆O₄

Average Mass

550.8961 Da

Monoisotopic Mass

550.49611 Da

IUPAC Name

3-(17,18-dihydroxytriacontyl)-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

3-(17,18-dihydroxytriacontyl)-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC(O)C(O)CCCCCCCCCCCCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C35H66O4/c1-3-4-5-6-7-8-16-19-22-25-28-33(36)34(37)29-26-23-20-17-14-12-10-9-11-13-15-18-21-24-27-32-30-31(2)39-35(32)38/h30-31,33-34,36-37H,3-29H2,1-2H3

InChI Key

NXSNZSWFXOMAOD-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
Annona atemoya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
1,2-diol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	9.85	ALOGPS
logP	11.78	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	166.48 m³·mol⁻¹	ChemAxon
Polarizability	74.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033605

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011693

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

129011027

PDB ID

Not Available

ChEBI ID

134013

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one (NP0146178)

MOL for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

3D MOL for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

3D SDF for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

3D-SDF for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

PDB for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

3D PDB for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

SMILES for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

INCHI for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

Structure for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)

3D Structure for NP0146178 (3-(17,18-dihydroxytriacontyl)-5-methyl-5h-furan-2-one)