NP-MRD: Showing NP-Card for (1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol (NP0245234)

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Record Information

Version

1.0

Created at

2022-09-07 06:14:38 UTC

Updated at

2022-09-07 06:14:38 UTC

NP-MRD ID

NP0245234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol

Description

Wattisine B belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. (1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol is found in Cyclea wattii. It was first documented in 2010 (PMID: 20606353). Based on a literature review very few articles have been published on Wattisine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208142D          

 43 49  0  0  1  0            999 V2000
    9.9015   -1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5876   -0.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    0.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9073    0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2089   -0.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4190    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1150    1.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846    1.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7553    1.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9956    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9389    1.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1450    1.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5431    0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7678   -0.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5811   -0.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107    1.9384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3568    2.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0926    3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1546    4.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360    4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603    5.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    4.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540    3.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074    2.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    2.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459    1.5904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071    4.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2549    4.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0938    4.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3908    4.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8974    5.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0719    5.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5808    6.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4785    3.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578    2.6436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6770    3.2127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4726    4.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4796    3.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6988    2.2183    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  1  1  0  0  0
 28 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
  8 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
  7 43  1  0  0  0  0
M  END

     RDKit          3D

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   -3.8784   -3.5059   -1.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2717   -2.1513   -1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6258   -1.9376   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5204   -2.9665   -1.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0990   -0.6658   -1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1686    0.3692   -0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8304    0.1924   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064   -1.1351   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0181   -1.3558   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -1.7232   -0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -1.5169   -1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5893   -1.8928   -1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358   -2.4819    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -2.6979    1.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -2.3115    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0615   -2.1647    1.4975 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9107   -0.7093    1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634    0.1689    1.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157    1.4777    1.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953    1.8733    0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    3.1975   -0.1790 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336    1.0312   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8876   -0.3011    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952   -1.1783   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1554   -2.4233    0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4719   -2.4881    1.5858 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1317   -1.7506    2.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1576    2.5240    1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    2.7348    1.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.9189    1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5470    2.3993    1.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480    3.6952    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408    4.5145    2.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    4.0186    2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5370    4.8794    2.5286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403    1.7948    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.3802   -0.6119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4433    2.4599   -1.4143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573    2.5316   -2.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245    2.6808   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    1.7535   -0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -5.1595   -2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0939   -3.5551   -3.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -3.9554   -2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5176   -2.8385   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1607   -0.4215   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537   -1.0487   -2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.5895   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -3.1475    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0844   -2.8429   -0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1713   -0.1215    2.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4345    3.8932    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6999    1.3317   -0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -1.3344   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456   -0.5804   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0309   -3.3566   -0.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9462    5.5133    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6618    2.5666    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    0.9682    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0235    1.6351   -3.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6731    2.6122   -2.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166    3.4191   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    3.7236   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7718    1.7613   -1.2040 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7 43  1  0
 43 42  1  0
 42 40  1  0
 40 41  1  0
 40 39  1  0
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 29 63  1  0
 29 64  1  0
 29 65  1  0
 18 55  1  1
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 17 54  1  0
 13 50  1  0
 12 49  1  0
 16 52  1  0
 15 51  1  0
 20 56  1  0
 32 66  1  0
M  END


  Mrv1652309072208142D          

 43 49  0  0  1  0            999 V2000
    9.9015   -1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5876   -0.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    0.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9073    0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2089   -0.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4190    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1150    1.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846    1.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7553    1.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9956    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1964    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9389    1.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1450    1.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5431    0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7678   -0.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5811   -0.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107    1.9384    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3568    2.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0926    3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1546    4.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360    4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603    5.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    4.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540    3.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074    2.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    2.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459    1.5904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071    4.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2549    4.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0938    4.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3908    4.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8974    5.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0719    5.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5808    6.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4785    3.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0578    2.6436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6770    3.2127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4726    4.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4796    3.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6988    2.2183    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  1  1  0  0  0
 28 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
  8 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
  7 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2CCN(C)[C@H]3CC4=CC=C(O)C(OC5=C(O)C=C6CCN(C)[C@H](CC7=CC=C(OC1=C23)C=C7)C6=C5)=C4

> <INCHI_IDENTIFIER>
InChI=1S/C35H36N2O6/c1-36-12-10-22-17-29(39)32-19-25(22)26(36)14-20-4-7-24(8-5-20)42-35-33-23(18-30(40)34(35)41-3)11-13-37(2)27(33)15-21-6-9-28(38)31(16-21)43-32/h4-9,16-19,26-27,38-40H,10-15H2,1-3H3/t26-,27+/m1/s1

> <INCHI_KEY>
UHKIRMGEDDVNBT-SXOMAYOGSA-N

> <FORMULA>
C35H36N2O6

> <MOLECULAR_WEIGHT>
580.681

> <EXACT_MASS>
580.257336887

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
62.952879385724785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,16S)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol

> <JCHEM_LOGP>
5.2103607005152135

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
8.96455846530034

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.490306194787303

> <JCHEM_PKA_STRONGEST_BASIC>
8.018436941005838

> <JCHEM_POLAR_SURFACE_AREA>
94.86

> <JCHEM_REFRACTIVITY>
166.66769999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,16S)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      18.483  -2.047   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.897  -0.623   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      18.837   0.596   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.360   0.360   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      20.923  -1.074   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      21.316   1.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.748   3.025   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.198   3.343   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.210   2.035   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.792   1.235   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.300   0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.819   2.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337   2.485   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.214   1.401   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.633  -0.118   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.151  -0.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.991   2.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.913   3.618   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.999   5.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.373   5.992   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.489   7.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.147   8.363   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.193   9.902   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.771   7.645   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.687   6.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.294   5.363   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.189   3.819   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       8.486   2.969   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       8.368   1.433   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.893   8.322   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.424   8.772   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.409   7.548   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.975   7.657   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.529   9.143   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.608  10.400   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.067  10.204   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.151  11.442   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      17.693   6.182   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.775   4.935   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      19.930   5.997   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      19.549   7.489   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      21.429   5.627   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      21.838   4.141   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   43                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   18   29                                                  
CONECT   29   28                                                            
CONECT   30   21   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36                                                            
CONECT   38   33   39                                                       
CONECT   39   38    8   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42    7                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₆N₂O₆

Average Mass

580.6810 Da

Monoisotopic Mass

580.25734 Da

IUPAC Name

(1R,16S)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol

Traditional Name

(1R,16S)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2CCN(C)[C@H]3CC4=CC=C(O)C(OC5=C(O)C=C6CCN(C)[C@H](CC7=CC=C(OC1=C23)C=C7)C6=C5)=C4

InChI Identifier

InChI=1S/C35H36N2O6/c1-36-12-10-22-17-29(39)32-19-25(22)26(36)14-20-4-7-24(8-5-20)42-35-33-23(18-30(40)34(35)41-3)11-13-37(2)27(33)15-21-6-9-28(38)31(16-21)43-32/h4-9,16-19,26-27,38-40H,10-15H2,1-3H3/t26-,27+/m1/s1

InChI Key

UHKIRMGEDDVNBT-SXOMAYOGSA-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
Cyclea wattii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Organonitrogen compound
Amine
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	5.21	ChemAxon
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.86 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	166.67 m³·mol⁻¹	ChemAxon
Polarizability	62.95 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

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

46849804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang JZ, Liu XY, Wang FP: Two new curine-type bisbenzylisoquinoline alkaloids from the roots of Cyclea wattii with cytotoxic activities. Chem Pharm Bull (Tokyo). 2010 Jul;58(7):986-8. doi: 10.1248/cpb.58.986. [PubMed:20606353 ]
LOTUS database [Link]

Showing NP-Card for (1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol (NP0245234)

MOL for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

3D MOL for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

3D SDF for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

3D-SDF for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

PDB for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

3D PDB for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

SMILES for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

INCHI for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

Structure for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)

3D Structure for NP0245234 ((1r,16s)-9-methoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18,20,22(33),24,26,31,35-dodecaene-10,21,25-triol)