NP-MRD: Showing NP-Card for methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate (NP0278903)

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Record Information

Version

2.0

Created at

2022-09-09 04:05:53 UTC

Updated at

2022-09-09 04:05:53 UTC

NP-MRD ID

NP0278903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate

Description

Methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-9-yl]-2-oxoacetate 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-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate is found in Azadirachta indica. Methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-9-yl]-2-oxoacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510282D          

 44 50  0  0  0  0            999 V2000
    0.3380    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    1.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693    2.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042    1.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    0.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642   -1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179   -0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -0.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6853   -1.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569   -1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119   -1.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -1.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918   -1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9129   -1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317    0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547    0.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    0.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.1734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931    1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    2.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    2.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7412    1.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500    0.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    0.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698    1.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4928    1.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    1.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9928    2.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3608    1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933    2.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244   -0.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1310    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8961    1.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    2.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    1.1673    0.0000 C   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
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 30 38  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  0  0  0  0
 21 40  1  0  0  0  0
  8 40  1  0  0  0  0
 17 40  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

 84 90  0  0  0  0  0  0  0  0999 V2000
    0.6172   -5.4628   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203   -4.1395   -1.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -3.0356   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139   -3.1665    0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -1.6551   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986   -1.5477   -1.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -0.4909    0.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2728   -0.0768    0.5077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2831    0.4162    1.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -1.2135    0.4549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4106   -1.7335    1.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156   -3.0607    2.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790   -3.4954    3.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2807   -3.9197    1.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6499   -0.7587    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9387    0.6827    0.3773 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2449    0.9394   -0.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2897    1.3864    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6513    1.6451    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0576    1.5723    1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0036    1.6080   -0.3121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5858    1.9344   -1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    2.8396    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1506    2.8912    0.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    2.0925   -0.7570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7130    0.8832   -0.5387 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5081    1.6712   -1.0722 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3892    1.0347   -2.3396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881    0.6303   -0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4579    1.4253    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067    0.1331   -0.6462 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3242   -0.4397   -1.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    0.5030   -1.5629 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5637    1.6835   -2.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.3037   -1.3590 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0854   -1.4745   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -0.6541    0.4286 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8975    0.2604    1.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2198    0.4087    0.9256 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5889    1.7440    1.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0009    2.4608    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0386    1.7116   -0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6219    0.3758   -0.5251 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7810   -0.4405   -0.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089   -5.9146   -0.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -6.0666   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577   -5.5191    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -0.9060    1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    0.0484    2.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -0.0438    2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3641    1.4749    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731   -1.9521   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536   -3.7163    3.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006   -4.4149    3.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261   -2.6540    4.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7800   -0.8936   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3817   -1.4025    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755    0.9088    1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6065    1.8705   -1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1173    2.4401    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2363    0.7191    0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    1.6378   -2.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166    3.0452   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651    1.4843   -1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701    3.7343   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9601    3.0605    1.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    2.5855   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764    0.3428   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.5200   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856    1.7347   -2.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7964    0.7980    1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406    2.2081    1.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3910    2.0026    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8961    2.5386   -1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133    1.4976   -3.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609    2.0590   -3.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -0.6873   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006   -1.9916    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4308   -2.1125   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5650   -1.2398    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8126   -0.2510    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2631    3.5141    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327    2.0583   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2820   -0.3825    0.2865 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  1
  8 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  6
 21 16  1  0
 16 15  1  0
 15 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  6
 32 33  1  0
 33 34  1  6
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  1  1
 29  7  1  0
 33 31  1  0
 43 35  1  0
 10  8  1  0
 37 31  1  0
 43 39  1  0
 21 26  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  7 48  1  1
  9 49  1  0
  9 50  1  0
  9 51  1  0
 26 68  1  6
 25 67  1  6
 23 65  1  0
 23 66  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 16 58  1  1
 15 56  1  0
 15 57  1  0
 10 52  1  6
 13 53  1  0
 13 54  1  0
 13 55  1  0
 19 59  1  0
 19 60  1  0
 19 61  1  0
 27 69  1  6
 28 70  1  0
 30 71  1  0
 30 72  1  0
 30 73  1  0
 34 74  1  0
 34 75  1  0
 34 76  1  0
 35 77  1  6
 36 78  1  0
 36 79  1  0
 37 80  1  1
 39 81  1  1
 41 82  1  0
 42 83  1  0
 44 84  1  0
M  END


  Mrv1533004241510282D          

 44 50  0  0  0  0            999 V2000
    0.3380    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    1.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693    2.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042    1.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    0.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    0.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642   -1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179   -0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -0.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6853   -1.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569   -1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119   -1.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -1.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918   -1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455   -0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9129   -1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317    0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547    0.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    0.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.1734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931    1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    2.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701    2.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7412    1.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500    0.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    0.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6698    1.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4928    1.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    1.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9928    2.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3608    1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933    2.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244   -0.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1310    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8961    1.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    2.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    1.1673    0.0000 C   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
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 30 38  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  0  0  0  0
 21 40  1  0  0  0  0
  8 40  1  0  0  0  0
 17 40  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=O)C1C2(C)C3C(OCC3(C)C(CC2OC(C)=O)OC(C)=O)C(O)C1(C)C12OC1(C)C1CC2OC2OC=CC12O

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O13/c1-13(32)41-16-11-17(42-14(2)33)27(4)21(19(34)24(36)38-7)28(5,23(35)20-22(27)26(16,3)12-40-20)31-18-10-15(29(31,6)44-31)30(37)8-9-39-25(30)43-18/h8-9,15-18,20-23,25,35,37H,10-12H2,1-7H3

> <INCHI_KEY>
VJZIPBVWTNJQPK-UHFFFAOYSA-N

> <FORMULA>
C31H40O13

> <MOLECULAR_WEIGHT>
620.648

> <EXACT_MASS>
620.246891348

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.06979395428603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
0.1564174849999988

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.914469972689734

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.17151449132723

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3985340594222793

> <JCHEM_POLAR_SURFACE_AREA>
176.65

> <JCHEM_REFRACTIVITY>
144.56780000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.631   3.743   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.615   2.838   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.022   3.464   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.183   4.996   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.268   2.559   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.674   3.185   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.107   1.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.700   0.401   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.645   1.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.029   1.027   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.275   0.122   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.114  -1.409   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.360  -2.315   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.767  -1.688   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.928  -0.157   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.013  -2.593   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.293  -2.036   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.852  -3.066   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.769  -3.500   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.309  -3.500   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.785  -2.036   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.192  -1.409   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.437  -2.315   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.353   0.122   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.889   0.015   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.301   1.336   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.020   2.190   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.400   2.872   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.617   4.198   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.664   3.753   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.984   1.998   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.440   0.299   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -7.960   0.544   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.717   1.885   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.253   1.993   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.626   3.487   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.320   4.303   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.140   3.313   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -7.827   4.821   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.539  -1.131   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.244   2.552   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.673   3.128   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.888   4.653   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.886   2.179   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   24                                                  
CONECT    8    7    9   10   40                                             
CONECT    9    8                                                            
CONECT   10    8   11   41                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19   40                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   40                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    7   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28   32                                             
CONECT   27   26   28                                                       
CONECT   28   27   26   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   30   34   39                                             
CONECT   39   38                                                            
CONECT   40   21    8   17                                                  
CONECT   41   10   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0,.0,]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0,]dodecan-9-yl]-2-oxoacetic acid	Generator
Methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetic acid	Generator

Chemical Formula

C₃₁H₄₀O₁₃

Average Mass

620.6480 Da

Monoisotopic Mass

620.24689 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C(=O)C1C2(C)C3C(OCC3(C)C(CC2OC(C)=O)OC(C)=O)C(O)C1(C)C12OC1(C)C1CC2OC2OC=CC12O

InChI Identifier

InChI=1S/C31H40O13/c1-13(32)41-16-11-17(42-14(2)33)27(4)21(19(34)24(36)38-7)28(5,23(35)20-22(27)26(16,3)12-40-20)31-18-10-15(29(31,6)44-31)30(37)8-9-39-25(30)43-18/h8-9,15-18,20-23,25,35,37H,10-12H2,1-7H3

InChI Key

VJZIPBVWTNJQPK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Azadirachta indica	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
Furopyran
Tricarboxylic acid or derivatives
Oxepane
Alpha-keto acid
Keto acid
Oxane
Pyran
Cyclic alcohol
Dihydrofuran
Furan
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Dialkyl ether
Oxirane
Ether
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.47	ALOGPS
logP	0.16	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	176.65 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	144.57 m³·mol⁻¹	ChemAxon
Polarizability	62.07 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate (NP0278903)

MOL for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

3D MOL for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

3D SDF for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

3D-SDF for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

PDB for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

3D PDB for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

SMILES for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

INCHI for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

Structure for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)

3D Structure for NP0278903 (methyl 2-[5,7-bis(acetyloxy)-11-hydroxy-10-{2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]dodec-3-en-9-yl}-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-9-yl]-2-oxoacetate)