NP-MRD: Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate (NP0320663)

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Record Information

Version

1.0

Created at

2022-09-11 22:26:36 UTC

Updated at

2022-09-11 22:26:36 UTC

NP-MRD ID

NP0320663

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate

Description

(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-11-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. (1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate is found in Melia azedarach. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on (1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-11-yl (2E)-2-methylbut-2-enoate (PMID: 27253005) (PMID: 27583328) (PMID: 36127157) (PMID: 36127156).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200262D          

 50 54  0  0  1  0            999 V2000
   -1.0486    3.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    3.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287    2.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    1.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934    2.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414    0.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6081    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6971    0.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5280    0.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383    0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239   -0.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6266   -1.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961   -2.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537   -2.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141   -3.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4437   -1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4650   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -2.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081   -3.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017   -4.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047   -4.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4429   -1.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019   -1.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -0.9421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9664   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240   -2.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245   -2.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617   -1.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092   -0.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    0.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2637    1.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8743    1.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974    1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    2.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    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  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 27 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 43  2  0  0  0  0
 38 44  1  0  0  0  0
 44 45  1  0  0  0  0
 35 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
 25 50  1  0  0  0  0
 50  9  1  1  0  0  0
 12 50  1  0  0  0  0
M  END

     RDKit          3D

100104  0  0  0  0  0  0  0  0999 V2000
   -1.0914    5.1597   -3.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    4.5054   -1.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    3.4336   -1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577    2.8868   -2.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5176    2.3609    2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1326    0.6994    1.8116 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4392    0.2400    3.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.2892    0.8055 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1224    1.3194    0.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4567    1.1137    0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5078    2.1504    0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -0.0333    1.3843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045   -0.0312   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796   -0.9149   -0.6333 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.8257   -1.2787   -2.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2259   -0.9192   -4.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0780   -1.0341    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122200262D          

 50 54  0  0  1  0            999 V2000
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   -1.2892    2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3346    1.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2414    0.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6081    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6971    0.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1383    0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239   -0.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6266   -1.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2961   -2.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0537   -2.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141   -3.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4437   -1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4650   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569   -2.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6081   -3.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017   -4.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1047   -4.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4429   -1.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5019   -1.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -0.9421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9664   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240   -2.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245   -2.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617   -1.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -1.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092   -0.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    0.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2637    1.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8743    1.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974    1.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    2.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    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  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 27 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 39 43  2  0  0  0  0
 38 44  1  0  0  0  0
 44 45  1  0  0  0  0
 35 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  2  0  0  0  0
 25 50  1  0  0  0  0
 50  9  1  1  0  0  0
 12 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320663

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@@H]1[C@@H]2OC[C@@]3(C)[C@H]2[C@](C)([C@H](C[C@H]3OC(C)=O)OC(C)=O)[C@@H](COC(C)=O)[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C38H50O12/c1-11-19(2)35(43)50-34-32-33-36(8,18-46-32)29(48-23(6)41)15-30(49-24(7)42)37(33,9)28(17-45-21(4)39)38(34,10)31-20(3)26(25-12-13-44-16-25)14-27(31)47-22(5)40/h11-13,16,26-30,32-34H,14-15,17-18H2,1-10H3/b19-11+/t26-,27+,28-,29-,30+,32-,33+,34-,36-,37+,38-/m1/s1

> <INCHI_KEY>
HXZMVLQJZGBXOD-ACTYCNGNSA-N

> <FORMULA>
C38H50O12

> <MOLECULAR_WEIGHT>
698.806

> <EXACT_MASS>
698.33022705

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
72.69532173659485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.4905680813333304

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8570960560216525

> <JCHEM_POLAR_SURFACE_AREA>
153.87

> <JCHEM_REFRACTIVITY>
177.86749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-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      -1.957   6.577   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.382   5.762   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.614   4.202   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.407   4.301   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.625   3.187   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.854   4.341   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.451   1.333   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.735   2.148   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.768   0.710   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.319   0.270   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.458   1.366   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.431  -0.880   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.770  -3.685   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.019  -4.760   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.434  -4.078   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.426  -6.322   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.561  -3.095   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.735  -3.977   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.786  -5.411   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.135  -6.979   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.430  -7.886   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.195  -7.874   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.827  -2.598   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.053  -1.156   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.937  -2.336   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.804  -3.621   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.365  -1.759   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.671  -2.575   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.778  -4.111   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.272  -4.484   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.088  -3.178   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -5.099  -1.998   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.257  -0.222   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.763   0.150   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.492   1.993   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.632   3.262   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.168   2.579   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -1.456   5.120   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       4.403  -0.010   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   33                                                  
CONECT    9    8   10   50                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   50                                             
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   27   50                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27    8   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36   45                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   39                                                       
CONECT   44   38   45                                                       
CONECT   45   44   35   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   25    9   12                                                  
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-Bis(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0,]dodecan-11-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₈H₅₀O₁₂

Average Mass

698.8060 Da

Monoisotopic Mass

698.33023 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@@H]1[C@@H]2OC[C@@]3(C)[C@H]2[C@](C)([C@H](C[C@H]3OC(C)=O)OC(C)=O)[C@@H](COC(C)=O)[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C38H50O12/c1-11-19(2)35(43)50-34-32-33-36(8,18-46-32)29(48-23(6)41)15-30(49-24(7)42)37(33,9)28(17-45-21(4)39)38(34,10)31-20(3)26(25-12-13-44-16-25)14-27(31)47-22(5)40/h11-13,16,26-30,32-34H,14-15,17-18H2,1-10H3/b19-11+/t26-,27+,28-,29-,30+,32-,33+,34-,36-,37+,38-/m1/s1

InChI Key

HXZMVLQJZGBXOD-ACTYCNGNSA-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
Melia azedarach	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
Pentacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
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
logP	3.49	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	153.87 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	177.87 m³·mol⁻¹	ChemAxon
Polarizability	72.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163002496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387 ]
Authors unspecified: Financial Toxicity and Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:27583328 ]
Gadot R, Najera R, Hirani S, Anand A, Storch E, Goodman WK, Shofty B, Sheth SA: Efficacy of deep brain stimulation for treatment-resistant obsessive-compulsive disorder: systematic review and meta-analysis. J Neurol Neurosurg Psychiatry. 2022 Sep 20. pii: jnnp-2021-328738. doi: 10.1136/jnnp-2021-328738. [PubMed:36127157 ]
Koggel LM, Lantinga MA, Buchner FL, Drenth JPH, Frankema JS, Heeregrave EJ, Heringa M, Numans ME, Siersema PD: Predictors for inappropriate proton pump inhibitor use: observational study in primary care. Br J Gen Pract. 2022 Jun 24. pii: BJGP.2022.0178. doi: 10.3399/BJGP.2022.0178. [PubMed:36127156 ]
LOTUS database [Link]

Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate (NP0320663)

MOL for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

PDB for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

Structure for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0320663 ((1r,4r,5r,7s,8r,9r,10r,11s,12r)-5,7-bis(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-[(acetyloxy)methyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl (2e)-2-methylbut-2-enoate)