NP-MRD: Showing NP-Card for (1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate (NP0322390)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 01:08:08 UTC

Updated at

2022-09-12 01:08:08 UTC

NP-MRD ID

NP0322390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate

Description

(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl (2E)-2-methylbut-2-enoate 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. (1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate is found in Swietenia mahagoni. Based on a literature review very few articles have been published on (1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203082D          

 43 48  0  0  1  0            999 V2000
   -2.4201    2.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205    1.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0584   -0.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213    0.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4216   -0.0241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7860   -0.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -0.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2363   -1.4599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5322   -2.2300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0131   -2.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3470   -2.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -1.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -3.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228   -1.3398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7487   -2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -0.5030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424    0.1214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3284    0.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    0.2191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1283    0.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9086   -0.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4765   -1.1954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8124   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -1.3574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4519   -2.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -1.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2728   -2.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0814   -2.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -3.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253   -3.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -2.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653   -0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    0.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 38  2  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 43 42  1  6  0  0  0
 27 43  1  0  0  0  0
 31 43  1  0  0  0  0
M  END

     RDKit          3D

 83 88  0  0  0  0  0  0  0  0999 V2000
   -4.0615   -4.4931    2.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3392   -3.4148    1.8673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808   -2.6027    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -2.7745    2.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6094   -1.5516    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7185   -1.3307   -0.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -0.7414    0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950    0.3241   -0.7825 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3576    1.6953   -0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.4659    1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4406    2.6523   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    2.2079   -0.3265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9331    3.7013   -0.0814 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4387    4.1327   -0.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919    4.1539    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6007    4.3322    1.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    4.3982    2.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902    4.8361    3.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2389    1.8349   -1.5855 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3160    3.0525   -2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940    1.3254   -2.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421    1.8820   -3.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8752    0.0430   -2.0554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7101   -0.4387   -3.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -0.9426   -1.9321 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0824   -0.7328   -3.1457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487   -0.5806   -1.7114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9005    0.8617   -1.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8382    1.1075   -0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3878   -0.1366    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8561   -1.0791   -0.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8263   -0.5234   -1.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029   -2.2308   -0.0490 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8506   -1.9914    0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5957   -0.8622    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8155   -1.1887    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905   -2.4653    1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6693   -3.0032    0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015   -3.4326   -0.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -3.8899   -1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -5.0463   -1.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295   -2.9046   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6148   -1.5759   -1.5063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2813   -4.2153    3.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9995   -4.7368    3.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7377   -5.4322    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3462   -3.3151    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -2.7025    3.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -3.7827    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072   -2.0353    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6698    0.3403   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6107    1.8794    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6908    0.3874    1.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530    1.8678    1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524    2.1079   -1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1108    3.5767   -1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794    2.7335    0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357    1.7813    0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436    4.3081   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    4.0082    0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8622    5.5322    3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700    3.9476    4.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2360    5.4083    4.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307    2.6359   -3.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097    3.8274   -2.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3178    3.3405   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0478   -1.3097   -2.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -1.9790   -1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437    1.0837   -2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479    1.7065   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    1.6884    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5559   -0.6260    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200    0.1399    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    0.5503   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8281   -1.0459   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.7651   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858   -2.5058    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3398    0.1352    0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6563   -0.5481    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -4.0245    1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -2.8142    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2833   -3.2765   -1.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.9451   -2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12  9  1  0
  9 10  1  0
  9 11  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
  8 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 27 26  1  6
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31 43  1  0
 43 42  1  0
 42 40  1  0
 40 41  2  0
 40 39  1  0
 39 33  1  0
 33 34  1  0
 34 38  2  0
 38 37  1  0
 37 36  1  0
 36 35  2  0
 28 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  2  0
 19 12  1  0
 21 23  1  0
 27 25  1  0
 43 27  1  0
 35 34  1  0
 33 31  1  0
 18 61  1  0
 18 62  1  0
 18 63  1  0
 13 59  1  6
 14 60  1  0
 12 58  1  1
 10 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 11 57  1  0
  8 51  1  6
  4 48  1  0
  4 49  1  0
  4 50  1  0
  2 47  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
 24 67  1  0
 25 68  1  1
 28 69  1  6
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 32 74  1  0
 32 75  1  0
 32 76  1  0
 43 83  1  6
 42 81  1  0
 42 82  1  0
 33 77  1  1
 38 80  1  0
 36 79  1  0
 35 78  1  0
 20 64  1  0
 20 65  1  0
 20 66  1  0
M  END


  Mrv1652309122203082D          

 43 48  0  0  1  0            999 V2000
   -2.4201    2.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205    1.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392    1.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0584   -0.2329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213    0.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4216   -0.0241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7860   -0.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -0.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2363   -1.4599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5322   -2.2300    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0131   -2.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3470   -2.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -1.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -3.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228   -1.3398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7487   -2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -0.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -0.5030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424    0.1214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3284    0.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    0.2191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1283    0.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9086   -0.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4765   -1.1954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8124   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -1.3574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4519   -2.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -1.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2728   -2.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0814   -2.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -3.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253   -3.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -2.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653   -0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    0.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 38  2  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 43 42  1  6  0  0  0
 27 43  1  0  0  0  0
 31 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O11/c1-8-15(2)23(35)42-26-28(3,4)21(20(34)24(36)39-7)30(6)17-9-11-29(5)18(32(17)27(43-32)31(26,38)25(30)37)13-19(33)41-22(29)16-10-12-40-14-16/h8,10,12,14,17-18,20-22,26-27,34,38H,9,11,13H2,1-7H3/b15-8+/t17-,18-,20+,21+,22+,26+,27-,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
OWNYIZYKHUQFKG-ZVPWTFETSA-N

> <FORMULA>
C32H40O11

> <MOLECULAR_WEIGHT>
600.661

> <EXACT_MASS>
600.257062108

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.720275866864824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.398189097

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.440062283780382

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.089694666927347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870491642025657

> <JCHEM_POLAR_SURFACE_AREA>
162.1

> <JCHEM_REFRACTIVITY>
147.7964

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.518   4.857   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.585   3.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.180   2.211   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.708   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.247   0.986   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.842  -0.435   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.720   1.181   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.787  -0.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.467  -1.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.754  -0.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.491  -2.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.441  -2.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.993  -4.163   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.025  -5.360   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.514  -4.403   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.483  -3.206   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.067  -5.841   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.588  -6.081   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.163  -2.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.397  -4.023   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.009  -1.128   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.538  -0.939   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.826   0.227   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.613   1.752   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.472   0.409   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.973   0.730   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.563  -0.815   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.756  -2.232   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.383  -3.639   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.908  -3.795   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.803  -2.534   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.444  -3.934   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.336  -2.680   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.976  -4.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.485  -4.386   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.661  -5.916   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.260  -6.556   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.219  -5.422   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.229  -1.425   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.589  -0.024   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.482   1.230   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.056   0.122   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.163  -1.133   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   12   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    8   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26   25   28   43                                             
CONECT   28   27   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33   43                                             
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   33   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   27   31                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(Furan-3-yl)-1-hydroxy-15-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0,.0,.0,]octadecan-17-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₁

Average Mass

600.6610 Da

Monoisotopic Mass

600.25706 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C32H40O11/c1-8-15(2)23(35)42-26-28(3,4)21(20(34)24(36)39-7)30(6)17-9-11-29(5)18(32(17)27(43-32)31(26,38)25(30)37)13-19(33)41-22(29)16-10-12-40-14-16/h8,10,12,14,17-18,20-22,26-27,34,38H,9,11,13H2,1-7H3/b15-8+/t17-,18-,20+,21+,22+,26+,27-,29-,30-,31+,32-/m1/s1

InChI Key

OWNYIZYKHUQFKG-ZVPWTFETSA-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
Swietenia mahagoni	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
Mexicanolide
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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

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

163185709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate (NP0322390)

MOL for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

PDB for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

Structure for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0322390 ((1s,2r,4s,5r,9r,10r,13r,14s,15s,17s)-9-(furan-3-yl)-1-hydroxy-15-[(1s)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl (2e)-2-methylbut-2-enoate)