NP-MRD: Showing NP-Card for 3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate (NP0285156)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 13:12:08 UTC

Updated at

2022-09-09 13:12:09 UTC

NP-MRD ID

NP0285156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Description

3-{[2-(3-Hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]Octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate is found in Erythroxylum pervillei. 3-{[2-(3-Hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]Octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251523362D          

 37 40  0  0  0  0            999 V2000
   -3.0639   -4.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1256   -3.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -0.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916   -1.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416   -1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666   -1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6791   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -3.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190   -2.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757   -3.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -4.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6390   -4.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957   -4.5488    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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 24 30  1  0  0  0  0
  5 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    6.2605   -2.7468    2.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0954   -2.2995    1.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6893   -1.3854    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4113   -0.8454    0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9703    0.0598   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.5596    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    1.4156   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6988    1.8556   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695    2.6885   -1.4214 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8567    1.4350    0.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.9308    0.4859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8108    2.5737    1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    1.7634    2.3154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2958    2.2702    1.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    1.6238    0.4686 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7171    0.6380    0.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9639    0.7350    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2194    1.7042   -0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0375   -0.2768    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3364   -0.9132   -0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6050   -2.0300   -1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8864   -2.6312   -2.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8482   -2.1796   -3.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5679   -1.0626   -2.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5502   -0.5536   -3.8120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3155   -0.4196   -1.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    1.0707   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3844    0.7223    0.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6834    0.4837    1.8134 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.6211    2.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8275    0.4730   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1140   -0.0600   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0266    0.3113   -2.0085 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6242    1.2485   -2.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446   -0.9704   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8187   -1.4691   -0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1074   -2.6357   -0.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401   -2.9994    2.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1798   -1.9676    3.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7199   -3.6344    3.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7425   -1.1766    1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802    0.1969    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506    1.7970   -1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850    2.6204   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    3.6387    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    2.3930    2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0463    1.8061    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489    3.3832    1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1100    2.0336    2.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280    2.4126   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6102   -1.0533    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9450    0.2096    0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332   -2.4570   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3264   -3.5161   -2.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0684   -2.6501   -4.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4118    0.1405   -4.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8892    0.4561   -1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    0.1746   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    1.8416   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663   -0.1237   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -1.2826    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929   -0.2608    2.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -1.2554    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408    1.1815   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1969    2.1704   -2.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8591    0.8816   -3.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5103    1.5242   -3.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7335   -2.4777   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6223   -3.3719   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1582   -3.0978   -1.2012 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
  5 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 36 37  1  0
 35  3  1  0
 28 11  1  0
 26 20  1  0
 29 13  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  6 42  1  0
  7 43  1  0
 11 44  1  6
 12 45  1  0
 12 46  1  0
 13 47  1  1
 14 48  1  0
 14 49  1  0
 15 50  1  6
 27 58  1  0
 27 59  1  0
 28 60  1  6
 30 61  1  0
 30 62  1  0
 30 63  1  0
 19 51  1  0
 19 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 26 57  1  0
 31 64  1  0
 34 65  1  0
 34 66  1  0
 34 67  1  0
 37 68  1  0
 37 69  1  0
 37 70  1  0
M  END


  Mrv1533004251523362D          

 37 40  0  0  0  0            999 V2000
   -3.0639   -4.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1256   -3.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -0.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916   -1.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416   -1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666   -1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6791   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -3.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190   -2.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757   -3.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -4.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6390   -4.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957   -4.5488    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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 24 30  1  0  0  0  0
  5 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OC2CC3CC(CC2N3C)OC(=O)CC2=CC=CC(O)=C2)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO8/c1-29-19-14-21(36-27(32)13-17-6-5-7-20(30)10-17)16-22(29)23(15-19)37-26(31)9-8-18-11-24(33-2)28(35-4)25(12-18)34-3/h5-12,19,21-23,30H,13-16H2,1-4H3

> <INCHI_KEY>
IYHVGWKIDIDOTL-UHFFFAOYSA-N

> <FORMULA>
C28H33NO8

> <MOLECULAR_WEIGHT>
511.571

> <EXACT_MASS>
511.220617027

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.087101882349145

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
3.2156751178339507

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.461420068097452

> <JCHEM_PKA_STRONGEST_BASIC>
8.209453402621032

> <JCHEM_POLAR_SURFACE_AREA>
103.76

> <JCHEM_REFRACTIVITY>
136.7233

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -5.719  -8.022   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.834  -6.487   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.562  -5.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.677  -4.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.405  -3.216   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.520  -1.680   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.247  -0.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.362   0.723   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.750   1.391   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.090   1.591   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.934   0.152   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.399   0.628   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.211   0.152   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.981  -1.181   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.211  -2.515   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.521  -1.181   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.291  -2.515   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.831  -2.515   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.601  -3.849   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.831  -5.182   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.291  -5.182   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.521  -6.516   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.521  -3.849   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.017  -3.884   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.902  -5.420   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.515  -6.088   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.400  -7.624   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.175  -6.287   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.059  -7.823   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.672  -8.491   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   24                                                       
CONECT   31    5   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32    3   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₃₃NO₈

Average Mass

511.5710 Da

Monoisotopic Mass

511.22062 Da

IUPAC Name

3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Traditional Name

3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OC2CC3CC(CC2N3C)OC(=O)CC2=CC=CC(O)=C2)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C28H33NO8/c1-29-19-14-21(36-27(32)13-17-6-5-7-20(30)10-17)16-22(29)23(15-19)37-26(31)9-8-18-11-24(33-2)28(35-4)25(12-18)34-3/h5-12,19,21-23,30H,13-16H2,1-4H3

InChI Key

IYHVGWKIDIDOTL-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
Erythroxylum pervillei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Tropane alkaloid
Anisole
Phenol ether
Styrene
Phenoxy compound
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.59	ALOGPS
logP	3.22	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.72 m³·mol⁻¹	ChemAxon
Polarizability	54.09 Å³	ChemAxon
Number of Rings	4	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

73878006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate (NP0285156)

MOL for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

3D MOL for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

3D SDF for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

3D-SDF for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

PDB for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

3D PDB for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

SMILES for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

INCHI for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

Structure for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)

3D Structure for NP0285156 (3-{[2-(3-hydroxyphenyl)acetyl]oxy}-8-methyl-8-azabicyclo[3.2.1]octan-6-yl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate)