NP-MRD: Showing NP-Card for methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate (NP0307690)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 00:59:49 UTC

Updated at

2022-09-11 00:59:50 UTC

NP-MRD ID

NP0307690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate

Description

Methyl 8alpha-hydroxy-8,30-dihydroangolensate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate is found in Heynea trijuga. methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate was first documented in 2008 (PMID: 18280524). Based on a literature review very few articles have been published on Methyl 8alpha-hydroxy-8,30-dihydroangolensate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202592D          

 35 39  0  0  1  0            999 V2000
    5.0636    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930    1.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8029    0.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616    0.0467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9019   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030    0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -1.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118   -1.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0008   -1.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605   -1.0624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5346   -1.1808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328   -0.4561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6679   -1.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -2.4041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -1.0400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314   -0.2368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1280    0.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    1.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    1.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.0072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3154    0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587    0.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076    0.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743    0.0226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4909   -0.2478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4587    0.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    0.4020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4623    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628    1.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 13 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
 30 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  6  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
    5.2430    2.8049    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    2.2709    0.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    1.2822   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3318    0.8901   -0.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0388    0.7066   -1.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -0.4434   -0.7152 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0706   -1.7150   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -2.1316   -1.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444   -1.7267    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653   -2.7722   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -3.8186    0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -2.5013   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -1.3607    0.3558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0648   -0.9993    0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177    0.0530    0.7915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2577   -0.4221    2.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3473   -1.3662    1.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704   -1.8860    2.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420   -1.6569    0.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4129   -0.6852   -0.6453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7158   -0.4727   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179   -0.2627   -2.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2737   -0.1027   -2.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8548   -0.2071   -1.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9727   -0.4251   -0.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621    0.5512   -0.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5826    1.5448    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8230    1.1142   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640    0.8798   -1.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    1.0001   -0.0150 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2168   -0.2059    0.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8502   -0.2298    1.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278    1.2505    0.9790 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3965    1.6340    2.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3100    2.4481    0.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652    3.3238    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6863    3.5391    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140    2.0220    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444    0.4340   -2.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3283    1.5458   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -0.7598   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.7370   -2.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -1.6388   -2.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -3.2249   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520   -2.6395    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4633   -0.9101    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2314   -1.9341   -0.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283   -2.3831   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -3.4055   -0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -1.8225    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    0.3733    2.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -1.0378    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7478   -1.1852   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650   -0.2280   -3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7896    0.0818   -3.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1523   -0.5572    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270    2.4707   -0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6531    1.2864    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3389    1.8133    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    2.1654   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206    0.5778   -2.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0458    1.6506   -2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1714   -0.0830   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    1.9297   -0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -0.3489    2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682   -1.2909    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6661    0.4321    1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7610    0.9097    3.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    2.5639    2.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580    1.9644    2.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705    3.0631    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  6
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 25  2  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 20 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 33  1  0
 33 34  1  0
 33 35  1  6
 30 31  1  0
 31 32  1  1
 31  6  1  0
 31 13  1  0
 26 15  1  0
 33 15  1  0
 22 21  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  6
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  1
 16 51  1  0
 16 52  1  0
 20 53  1  6
 25 56  1  0
 23 55  1  0
 22 54  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  0
 28 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  6
 34 68  1  0
 34 69  1  0
 34 70  1  0
 35 71  1  0
 32 65  1  0
 32 66  1  0
 32 67  1  0
M  END


  Mrv1652309112202592D          

 35 39  0  0  1  0            999 V2000
    5.0636    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930    1.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8029    0.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616    0.0467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9019   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030    0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -1.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118   -1.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0008   -1.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605   -1.0624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5346   -1.1808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328   -0.4561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6679   -1.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215   -1.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -2.4041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -1.0400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314   -0.2368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1280    0.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    1.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    1.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    0.0072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3154    0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587    0.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076    0.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5743    0.0226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4909   -0.2478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4587    0.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    0.4020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4623    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628    1.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 13 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
 30 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0307690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)C(=O)C[C@@H]2O[C@]34CC(=O)O[C@@H](C5=COC=C5)[C@]3(C)CC[C@@H]([C@@]4(C)O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O8/c1-23(2)17(11-20(29)32-6)25(4)16-7-9-24(3)22(15-8-10-33-14-15)34-21(30)13-27(24,26(16,5)31)35-19(25)12-18(23)28/h8,10,14,16-17,19,22,31H,7,9,11-13H2,1-6H3/t16-,17+,19+,22+,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
AJGPLSFXCODLPT-PQNFZEBCSA-N

> <FORMULA>
C27H36O8

> <MOLECULAR_WEIGHT>
488.577

> <EXACT_MASS>
488.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.663355865606924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,3S,7R,8S,9R,12S,13R,17R)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

> <JCHEM_LOGP>
3.0067013073333317

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.59056755286878

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.615092352608329

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8691532038362975

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000002

> <JCHEM_REFRACTIVITY>
123.1467

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,3S,7R,8S,9R,12S,13R,17R)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

> <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       9.452   4.228   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.014   3.678   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.770   2.157   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.965   1.186   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.332   1.608   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.088   0.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.283  -0.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.032   0.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.739  -1.388   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.040  -2.405   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.235  -3.376   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.602  -2.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.406  -1.983   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.865  -2.204   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.928  -0.851   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.247  -2.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.227  -2.974   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.511  -4.488   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.362  -1.941   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.992  -0.442   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.106   0.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.621   0.346   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.351   1.701   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.288   2.815   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.900   2.148   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.547   0.013   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.589   1.053   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.856   1.547   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.441   1.774   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.939   0.042   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.650  -0.462   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.590   1.076   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.485   0.750   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.596   1.817   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.477   2.290   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26   33                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26   20   15   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   13    6   32                                             
CONECT   32   31                                                            
CONECT   33   30   15   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 8a-hydroxy-8,30-dihydroangolensate	Generator
Methyl 8a-hydroxy-8,30-dihydroangolensic acid	Generator
Methyl 8alpha-hydroxy-8,30-dihydroangolensic acid	Generator
Methyl 8α-hydroxy-8,30-dihydroangolensate	Generator
Methyl 8α-hydroxy-8,30-dihydroangolensic acid	Generator

Chemical Formula

C₂₇H₃₆O₈

Average Mass

488.5770 Da

Monoisotopic Mass

488.24102 Da

IUPAC Name

methyl 2-[(1R,3S,7R,8S,9R,12S,13R,17R)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

Traditional Name

methyl [(1R,3S,7R,8S,9R,12S,13R,17R)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)C(=O)C[C@@H]2O[C@]34CC(=O)O[C@@H](C5=COC=C5)[C@]3(C)CC[C@@H]([C@@]4(C)O)[C@]12C

InChI Identifier

InChI=1S/C27H36O8/c1-23(2)17(11-20(29)32-6)25(4)16-7-9-24(3)22(15-8-10-33-14-15)34-21(30)13-27(24,26(16,5)31)35-19(25)12-18(23)28/h8,10,14,16-17,19,22,31H,7,9,11-13H2,1-6H3/t16-,17+,19+,22+,24+,25-,26-,27-/m1/s1

InChI Key

AJGPLSFXCODLPT-PQNFZEBCSA-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
Heynea trijuga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	3.01	ChemAxon
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.15 m³·mol⁻¹	ChemAxon
Polarizability	50.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

101855134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang XN, Fan CQ, Yin S, Gan LS, Yue JM: Structural elucidation of limonoids and steroids from Trichilia connaroides. Phytochemistry. 2008 Apr;69(6):1319-27. doi: 10.1016/j.phytochem.2008.01.018. Epub 2008 Feb 15. [PubMed:18280524 ]
LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate (NP0307690)

MOL for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

3D MOL for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

3D SDF for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

3D-SDF for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

PDB for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

3D PDB for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

SMILES for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

INCHI for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

Structure for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)

3D Structure for NP0307690 (methyl 2-[(1r,3s,7r,8s,9r,12s,13s,17r)-13-(furan-3-yl)-17-hydroxy-6,6,8,12,17-pentamethyl-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0¹,¹².0³,⁸]heptadecan-7-yl]acetate)