NP-MRD: Showing NP-Card for protopine (NP0030595)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-06-19 21:54:38 UTC

Updated at

2021-08-20 00:00:19 UTC

NP-MRD ID

NP0030595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

protopine

Provided By

JEOL Database JEOL Logo

Description

Protopine, also known as corydinine or fumarine, belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Protopine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make protopine a potential biomarker for the consumption of these foods. Protopine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. protopine is found in Arctomecon merriamii, Argemone grandiflora, Argemone munita, Argemone ochroleuca, Argemone platyceras, Argemone subfusiformis, Berberis darwinii, Berberis empetrifolia, Berberis laurina, Berberis microphylla, Bocconia frutescens, Bocconia latisepala, Caltha palustris, Chelidonium majus L. , Chelidonum majus, Corydalis ambigua, Corydalis balansae, Corydalis cheilanthifolia, Corydalis heterocarpa, Corydalis incisa, Corydalis ledebouriana, Corydalis ophiocarpa, Corydalis saxicola, Capnoides sempervirens, Corydalis speciosa, Corydalis tashiro, Cyclea atjehensis, Dactylicapnos torulosa, Dactylocapnos torulosa, Dicentra formosa, Dicentra peregrina, Fumaria asepala , Fumaria bella, Fumaria bracteosa, Fumaria cilicica, Fumaria gaillardotii, Fumaria judaica, Fumaria kralikii, Fumaria macrocarpa, Fumaria macrosepala, Fumaria officinalis, Fumaria petteri, Fumaria rostellata, Fumaria schramii, Fumaria sepium, Fumaria spicata, Galanthus trojanus, Glaucium leiocarpum, Glaucium squamigerum, Hunnemannia fumariifolia, Hylomecon japonica, Hypecoum erectum, Hypecoum imberbe, Hypecoum pendulum, Ichtyoselmis macrantha, Meconopsis napaulensis, Papaver atlanticum, Papaver canescens, Papaver heterophyllum, Papaver kerneri, Papaver lapponicum, Papaver lateritium, Papaver nudicaule, Papaver orientale, Papaver pavoninum, Papaver pygmaeum, Papaver rhoeas, Papaver tatricum, Platystemon californicus, Roemeria refracta, Sanguinaria canadensis, Sarcocapnos crassifolia, Stylophorum diphyllum, Stylophorum lasiocarpum, Thalictrum delavayi, Thalictrum foetidum, Thalictrum minus, Thalictrum thunbergii and Thalictrum revolutum. It was first documented in 2003 (PMID: 12726842). Based on a literature review a small amount of articles have been published on Protopine (PMID: 22029392) (PMID: 15458726) (PMID: 15588728).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123543D          

 45 49  0  0  0  0            999 V2000
    0.2588   -0.7050   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.5104   -1.6746 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0385   -1.4446   -2.2812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3571   -1.5980   -1.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1789   -2.2414   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -3.6324   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -4.2215    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -3.4916    2.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1313    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949   -1.5046    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670   -0.0412    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    0.7030    0.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    0.4196    1.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7167    1.6901    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    2.7034    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    3.8885    0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    4.0437   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0739   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    1.8719   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    0.8930   -1.8498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3835    3.4502   -2.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221    4.7558   -2.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6293    5.1334   -1.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6788   -4.2633    3.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124   -5.5635    2.9030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3183   -5.5453    1.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.7289   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.5217   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996   -0.0466   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   -2.4421   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -1.1375   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.6497   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2280   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -4.2412   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5751    3.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.5616    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.3734    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.5674    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    4.6594    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.0090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    1.1851   -2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    5.4948   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    4.7655   -3.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -6.2376    3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -5.9515    3.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  2  0  0  0  0
  5  4  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 17  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  6  7  2  0  0  0  0
  5 10  2  0  0  0  0
  8  9  2  0  0  0  0
 17 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 18  1  0  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
  2 20  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 19 20  1  0  0  0  0
  7 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24  8  1  0  0  0  0
 11 12  2  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
  9 35  1  0  0  0  0
  6 34  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    0.2588   -0.7050   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.5104   -1.6746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385   -1.4446   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3571   -1.5980   -1.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -2.2414   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -3.6324   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -4.2215    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -3.4916    2.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1313    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949   -1.5046    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670   -0.0412    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    0.7030    0.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    0.4196    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167    1.6901    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    2.7034    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    3.8885    0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    4.0437   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0739   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    1.8719   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    0.8930   -1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    3.4502   -2.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221    4.7558   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    5.1334   -1.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6788   -4.2633    3.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124   -5.5635    2.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -5.5453    1.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.7289   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.5217   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996   -0.0466   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   -2.4421   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -1.1375   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.6497   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2280   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -4.2412   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5751    3.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.5616    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.3734    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.5674    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    4.6594    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.0090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    1.1851   -2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    5.4948   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    4.7655   -3.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -6.2376    3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -5.9515    3.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  2  0
  5  4  1  0
 14 15  1  0
 10 11  1  0
 15 16  2  0
 16 17  1  0
 18 19  1  0
 18 17  2  0
  2  3  1  0
  3  4  1  0
  6  7  2  0
  5 10  2  0
  8  9  2  0
 17 23  1  0
 23 22  1  0
 22 21  1  0
 21 18  1  0
  8  7  1  0
  9 10  1  0
  2 20  1  0
 11 13  1  0
 13 14  1  0
 19 20  1  0
  7 26  1  0
 26 25  1  0
 25 24  1  0
 24  8  1  0
 11 12  2  0
  5  6  1  0
  2  1  1  0
  9 35  1  0
  6 34  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
 13 36  1  0
 13 37  1  0
 20 40  1  0
 20 41  1  0
 15 38  1  0
 16 39  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652306192123543D          

 45 49  0  0  0  0            999 V2000
    0.2588   -0.7050   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.5104   -1.6746 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0385   -1.4446   -2.2812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3571   -1.5980   -1.4931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1789   -2.2414   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -3.6324   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -4.2215    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -3.4916    2.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1313    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949   -1.5046    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670   -0.0412    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    0.7030    0.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    0.4196    1.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7167    1.6901    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    2.7034    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    3.8885    0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    4.0437   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0739   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    1.8719   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    0.8930   -1.8498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3835    3.4502   -2.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221    4.7558   -2.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6293    5.1334   -1.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6788   -4.2633    3.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124   -5.5635    2.9030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3183   -5.5453    1.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.7289   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.5217   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996   -0.0466   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   -2.4421   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -1.1375   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.6497   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2280   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -4.2412   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5751    3.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.5616    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.3734    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.5674    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    4.6594    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.0090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    1.1851   -2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    5.4948   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    4.7655   -3.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -6.2376    3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -5.9515    3.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  2  0  0  0  0
  5  4  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 17  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  6  7  2  0  0  0  0
  5 10  2  0  0  0  0
  8  9  2  0  0  0  0
 17 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 18  1  0  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
  2 20  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 19 20  1  0  0  0  0
  7 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24  8  1  0  0  0  0
 11 12  2  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
  9 35  1  0  0  0  0
  6 34  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 20 40  1  0  0  0  0
 20 41  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(C3=C1OC([H])([H])O3)C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C1=C(C([H])=C3OC([H])([H])OC3=C1[H])C(=O)C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

> <INCHI_KEY>
GPTFURBXHJWNHR-UHFFFAOYSA-N

> <FORMULA>
C20H19NO5

> <MOLECULAR_WEIGHT>
353.3686

> <EXACT_MASS>
353.126322723

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.68135899239593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.592985362999999

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.81658550426323

> <JCHEM_PKA_STRONGEST_BASIC>
4.862612519952881

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
94.56880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    0.2588   -0.7050   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.5104   -1.6746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385   -1.4446   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3571   -1.5980   -1.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -2.2414   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -3.6324   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -4.2215    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -3.4916    2.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1313    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949   -1.5046    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670   -0.0412    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    0.7030    0.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    0.4196    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167    1.6901    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    2.7034    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    3.8885    0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    4.0437   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0739   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    1.8719   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    0.8930   -1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    3.4502   -2.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221    4.7558   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    5.1334   -1.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6788   -4.2633    3.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124   -5.5635    2.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -5.5453    1.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.7289   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.5217   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996   -0.0466   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   -2.4421   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -1.1375   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.6497   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2280   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -4.2412   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5751    3.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.5616    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.3734    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.5674    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    4.6594    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.0090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    1.1851   -2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    5.4948   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    4.7655   -3.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -6.2376    3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -5.9515    3.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  2  0
  5  4  1  0
 14 15  1  0
 10 11  1  0
 15 16  2  0
 16 17  1  0
 18 19  1  0
 18 17  2  0
  2  3  1  0
  3  4  1  0
  6  7  2  0
  5 10  2  0
  8  9  2  0
 17 23  1  0
 23 22  1  0
 22 21  1  0
 21 18  1  0
  8  7  1  0
  9 10  1  0
  2 20  1  0
 11 13  1  0
 13 14  1  0
 19 20  1  0
  7 26  1  0
 26 25  1  0
 25 24  1  0
 24  8  1  0
 11 12  2  0
  5  6  1  0
  2  1  1  0
  9 35  1  0
  6 34  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
 13 36  1  0
 13 37  1  0
 20 40  1  0
 20 41  1  0
 15 38  1  0
 16 39  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.259  -0.705  -2.264  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.071  -0.510  -1.675  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.038  -1.445  -2.281  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.357  -1.598  -1.493  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.179  -2.241  -0.134  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.366  -3.632  -0.016  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.177  -4.221   1.217  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.811  -3.492   2.322  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.612  -2.131   2.260  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.795  -1.505   1.017  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.567  -0.041   0.960  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.526   0.703   0.781  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.143   0.420   1.206  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.717   1.690   0.491  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.108   2.703   1.281  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.367   3.889   0.716  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.230   4.044  -0.641  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.348   3.074  -1.429  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.827   1.872  -0.913  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.504   0.893  -1.850  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.384   3.450  -2.741  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.222   4.756  -2.678  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.629   5.133  -1.350  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.679  -4.263   3.433  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.012  -5.564   2.903  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.318  -5.545   1.493  0.00  0.00           O+0
HETATM   27  H   UNK     0       0.607  -1.729  -2.088  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.263  -0.522  -3.344  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.000  -0.047  -1.798  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.583  -2.442  -2.349  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.268  -1.137  -3.310  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.894  -0.650  -1.397  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.031  -2.228  -2.090  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.651  -4.241  -0.869  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.335  -1.575   3.148  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.061   0.562   2.292  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.433  -0.373   0.945  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.003   2.567   2.356  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.824   4.659   1.325  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.578   1.009  -1.671  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.360   1.185  -2.898  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.498   5.495  -3.049  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.102   4.766  -3.331  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.164  -6.238   3.069  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.882  -5.952   3.446  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3   20    1                                                  
CONECT    3    2    4   30   31                                             
CONECT    4    5    3   32   33                                             
CONECT    5    4   10    6                                                  
CONECT    6    7    5   34                                                  
CONECT    7    6    8   26                                                  
CONECT    8    9    7   24                                                  
CONECT    9    8   10   35                                                  
CONECT   10   11    5    9                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14   36   37                                             
CONECT   14   19   15   13                                                  
CONECT   15   14   16   38                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   18   23                                                  
CONECT   18   19   17   21                                                  
CONECT   19   14   18   20                                                  
CONECT   20    2   19   40   41                                             
CONECT   21   22   18                                                       
CONECT   22   23   21   42   43                                             
CONECT   23   17   22                                                       
CONECT   24   25    8                                                       
CONECT   25   26   24   44   45                                             
CONECT   26    7   25                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    6                                                            
CONECT   35    9                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   25                                                            
CONECT   45   25                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

RDKit          3D

45 49  0  0  0  0  0  0  0  0999 V2000
    0.2588   -0.7050   -2.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.5104   -1.6746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385   -1.4446   -2.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3571   -1.5980   -1.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1789   -2.2414   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -3.6324   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -4.2215    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -3.4916    2.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1313    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949   -1.5046    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670   -0.0412    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    0.7030    0.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    0.4196    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167    1.6901    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    2.7034    1.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    3.8885    0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2298    4.0437   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0739   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272    1.8719   -0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    0.8930   -1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    3.4502   -2.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221    4.7558   -2.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    5.1334   -1.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6788   -4.2633    3.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124   -5.5635    2.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -5.5453    1.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.7289   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -0.5217   -3.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9996   -0.0466   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835   -2.4421   -2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675   -1.1375   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -0.6497   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0313   -2.2280   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6506   -4.2412   -0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5751    3.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.5616    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.3734    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    2.5674    2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235    4.6594    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.0090   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    1.1851   -2.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    5.4948   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1021    4.7655   -3.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -6.2376    3.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -5.9515    3.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 14  2  0
  5  4  1  0
 14 15  1  0
 10 11  1  0
 15 16  2  0
 16 17  1  0
 18 19  1  0
 18 17  2  0
  2  3  1  0
  3  4  1  0
  6  7  2  0
  5 10  2  0
  8  9  2  0
 17 23  1  0
 23 22  1  0
 22 21  1  0
 21 18  1  0
  8  7  1  0
  9 10  1  0
  2 20  1  0
 11 13  1  0
 13 14  1  0
 19 20  1  0
  7 26  1  0
 26 25  1  0
 25 24  1  0
 24  8  1  0
 11 12  2  0
  5  6  1  0
  2  1  1  0
  9 35  1  0
  6 34  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
 13 36  1  0
 13 37  1  0
 20 40  1  0
 20 41  1  0
 15 38  1  0
 16 39  1  0
 22 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one	ChEBI
7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one	ChEBI
Corydinine	ChEBI
Fumarine	ChEBI
Macleyine	ChEBI
Biflorine	HMDB
Hypercorine	HMDB
Protopin	HMDB
Protopine mesylate	HMDB
Protopine hydrochloride	HMDB

Chemical Formula

C₂₀H₁₉NO₅

Average Mass

353.3686 Da

Monoisotopic Mass

353.12632 Da

IUPAC Name

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

Traditional Name

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(C3=C1OC([H])([H])O3)C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C1=C(C([H])=C3OC([H])([H])OC3=C1[H])C(=O)C2([H])[H]

InChI Identifier

InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

InChI Key

GPTFURBXHJWNHR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Annona squamosa	KNApSAcK Database	22123792
Anser anser	FooDB	FooDB
Arctomecon californica	KNApSAcK Database	22123792
Arctomecon humilis	KNApSAcK Database	22123792
Arctomecon merriamii	LOTUS Database	35616633
Arctomecon merrianii	KNApSAcK Database	22123792
Argemone grandiflora	LOTUS Database	35616633
Argemone mexicana	KNApSAcK Database	22123792
Argemone munita	LOTUS Database	35616633
Argemone ochroleuca	LOTUS Database	35616633
Argemone platyceras	LOTUS Database	35616633
Argemone subfusiformia	KNApSAcK Database	22123792
Argemone subfusiformis	LOTUS Database	35616633
Argemone subfusiformis var.subinermis	KNApSAcK Database	22123792
Berberis darwinii	LOTUS Database	35616633
Berberis empetrifolia	LOTUS Database	35616633
Berberis laurina	LOTUS Database	35616633
Berberis microphylla	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bocconia frutescens	LOTUS Database	35616633
Bocconia latisepala	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Caltha palustris	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chelidonium majus	Plant	KNApSAcK
Chelidonium majus L.	KNApSAcK Database	22123792
Chelidonum majus	-	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corydalis adunca	KNApSAcK Database	22123792
Corydalis ambigua	LOTUS Database	35616633
Corydalis ambigua var.amurensis	KNApSAcK Database	22123792
Corydalis balansae	LOTUS Database	35616633
Corydalis bungeana	KNApSAcK Database	22123792
Corydalis caucasia	KNApSAcK Database	22123792
Corydalis cava	KNApSAcK Database	22123792
Corydalis cheilanthifolia	LOTUS Database	35616633
Corydalis claviculata	KNApSAcK Database	22123792
Corydalis decumbens	KNApSAcK Database	22123792
Corydalis esquirolii	KNApSAcK Database	22123792
Corydalis gigantea Trautv.et Mey.	KNApSAcK Database	22123792
Corydalis glaucescens	KNApSAcK Database	22123792
Corydalis gortschakovii	KNApSAcK Database	22123792
Corydalis heterocarpa	LOTUS Database	35616633
Corydalis hsuchowensis	KNApSAcK Database	22123792
Corydalis incisa	LOTUS Database	35616633
Corydalis intermedia	KNApSAcK Database	22123792
Corydalis ledebouriana	LOTUS Database	35616633
Corydalis ledebouriana K.et K.	KNApSAcK Database	22123792
Corydalis longicalcarata	KNApSAcK Database	22123792
Corydalis majori	KNApSAcK Database	22123792
Corydalis nobilis	KNApSAcK Database	22123792
Corydalis omeiensis	KNApSAcK Database	22123792
Corydalis ophiocarpa	LOTUS Database	35616633
Corydalis pallida	KNApSAcK Database	22123792
Corydalis pseudoadunca	KNApSAcK Database	22123792
Corydalis racemosa	KNApSAcK Database	22123792
Corydalis remota	KNApSAcK Database	22123792
Corydalis repens	KNApSAcK Database	22123792
Corydalis saxicola	LOTUS Database	35616633
Corydalis sempervirens	LOTUS Database	35616633
Corydalis sewerzovii	KNApSAcK Database	22123792
Corydalis solida	KNApSAcK Database	22123792
Corydalis speciosa	LOTUS Database	35616633
Corydalis stricta Steph.	KNApSAcK Database	22123792
Corydalis suaveolens	KNApSAcK Database	22123792
Corydalis tashiro	Plant	KNApSAcK
Corydalis thyrsifolia	KNApSAcK Database	22123792
Corydalis turtschaninowii	KNApSAcK Database	22123792
Corydalis yanhusuo	KNApSAcK Database	22123792
Cyclea atjehensis	LOTUS Database	35616633
Dactylicapnos torulosa	LOTUS Database	35616633
Dactylocapnos torulosa	-	KNApSAcK
Dicentra formosa	LOTUS Database	35616633
Dicentra peregrina	LOTUS Database	35616633
Dicentra spectabilis	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Eomecon chionantha	KNApSAcK Database	22123792
Equus caballus	FooDB	FooDB
Eschscholzia californica	KNApSAcK Database	22123792
Fumaria agraria	KNApSAcK Database	22123792
Fumaria asepala	Plant	KNApSAcK
Fumaria bastardii	KNApSAcK Database	22123792
Fumaria bella	Plant	KNApSAcK
Fumaria bracteosa	LOTUS Database	35616633
Fumaria capreolata	KNApSAcK Database	22123792
Fumaria cilicica	Plant	KNApSAcK
Fumaria densiflora	KNApSAcK Database	22123792
Fumaria gaillardotii	Plant	KNApSAcK
Fumaria indica	KNApSAcK Database	22123792
Fumaria judaica	Plant	KNApSAcK
Fumaria kralikii	Plant	KNApSAcK
Fumaria macrocarpa	Plant	KNApSAcK
Fumaria macrosepala	LOTUS Database	35616633
Fumaria muralis	KNApSAcK Database	22123792
Fumaria officinalis	JEOL database	Seger, C., et al, Magn. Reson. Chem. 42, 882 (2004)
Fumaria parviflora	KNApSAcK Database	22123792
Fumaria petteri	Plant	KNApSAcK
Fumaria rostellata	LOTUS Database	35616633
Fumaria schleicheri	KNApSAcK Database	22123792
Fumaria schramii	Plant	KNApSAcK
Fumaria sepium	Plant	KNApSAcK
Fumaria spicata	Plant	KNApSAcK
Fumaria vaillantii	KNApSAcK Database	22123792
Galanthus trojanus	LOTUS Database	35616633
Gallium aparine	KNApSAcK Database	22123792
Gallus gallus	FooDB	FooDB
Glaucium arabicum	KNApSAcK Database	22123792
Glaucium corniculatum	KNApSAcK Database	22123792
Glaucium fimbrilligerum	KNApSAcK Database	22123792
Glaucium flavum	KNApSAcK Database	22123792
Glaucium grandiflorum	KNApSAcK Database	22123792
Glaucium leiocarpum	LOTUS Database	35616633
Glaucium squamigerum	LOTUS Database	35616633
Hunnemannia fumariaefolia	LOTUS Database	35616633
Hunnemannia fumariaefolia Sweet.	KNApSAcK Database	22123792
Hylomecon japonica	LOTUS Database	35616633
Hypecoum erectum	LOTUS Database	35616633
Hypecoum erectum L.	KNApSAcK Database	22123792
Hypecoum imberbe	LOTUS Database	35616633
Hypecoum leptocarpum	KNApSAcK Database	22123792
Hypecoum pendulum	LOTUS Database	35616633
Hypecoum pendulum L.	KNApSAcK Database	22123792
Hypecoum procumbens	KNApSAcK Database	22123792
Hypecoum trilobum	KNApSAcK Database	22123792
Ichtyoselmis macrantha	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Macleaya cordata	KNApSAcK Database	22123792
Meconopsis cambrica	KNApSAcK Database	22123792
Meconopsis napaulensis	LOTUS Database	35616633
Meconopsis robusta	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Nandina domestica	KNApSAcK Database	22123792
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oldenlandia biflora	KNApSAcK Database	22123792
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Papaver albiforum	KNApSAcK Database	22123792
Papaver argemone	KNApSAcK Database	22123792
Papaver atlanticum	LOTUS Database	35616633
Papaver bracteatum	KNApSAcK Database	22123792
Papaver californicum	KNApSAcK Database	22123792
Papaver canescens	LOTUS Database	35616633
Papaver confine	KNApSAcK Database	22123792
Papaver curviscapum	KNApSAcK Database	22123792
Papaver dubium	KNApSAcK Database	22123792
Papaver fugax	KNApSAcK Database	22123792
Papaver heterophyllum	LOTUS Database	35616633
Papaver kerneri	Plant	KNApSAcK
Papaver lapponicum	LOTUS Database	35616633
Papaver lateritium	LOTUS Database	35616633
Papaver macrostomum	KNApSAcK Database	22123792
Papaver nudicaule	LOTUS Database	35616633
Papaver orientale	LOTUS Database	35616633
Papaver orientale L.	KNApSAcK Database	22123792
Papaver pavoninum	LOTUS Database	35616633
Papaver persicum Lindl.	KNApSAcK Database	22123792
Papaver pinnatifidum	KNApSAcK Database	22123792
Papaver pygmaeum	LOTUS Database	35616633
Papaver radicatum	KNApSAcK Database	22123792
Papaver rhoeas	LOTUS Database	35616633
Papaver rhoeas chelidonides	KNApSAcK Database	22123792
Papaver rhopalothece	KNApSAcK Database	22123792
Papaver somniferum	KNApSAcK Database	22123792
Papaver stevenianum	KNApSAcK Database	22123792
Papaver tatricum	Plant	KNApSAcK
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Platycapnos saxicola	KNApSAcK Database	22123792
Platycapnos spicata	KNApSAcK Database	22123792
Platystemon californicus	LOTUS Database	35616633
Roemeria refracta	LOTUS Database	35616633
Sanguinaria canadensis	LOTUS Database	35616633
Sarcocapnos baetica	KNApSAcK Database	22123792
Sarcocapnos crassifolia	LOTUS Database	35616633
Sarcocapnos enneaphylla	KNApSAcK Database	22123792
Sarcocapnos saetabensis	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Stylophorum diphyllum	LOTUS Database	35616633
Stylophorum lasiocarpum	LOTUS Database	35616633
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Thalictrum atriplex	KNApSAcK Database	22123792
Thalictrum delavayi	LOTUS Database	35616633
Thalictrum faberi	KNApSAcK Database	22123792
Thalictrum flavum	KNApSAcK Database	22123792
Thalictrum foetidum	LOTUS Database	35616633
Thalictrum foliolosum	KNApSAcK Database	22123792
Thalictrum gladulosissimum	KNApSAcK Database	22123792
Thalictrum glandulosissimum	KNApSAcK Database	22123792
Thalictrum isopyroides	KNApSAcK Database	22123792
Thalictrum microgyum	KNApSAcK Database	22123792
Thalictrum minus	LOTUS Database	35616633
Thalictrum minus var. hypoleucum	Plant	KNApSAcK
Thalictrum petaloideum	KNApSAcK Database	22123792
Thalictrum revolutum	LOTUS Database	35616633
Thalictrum simplex	KNApSAcK Database	22123792
Thalictrum thunbergii	KNApSAcK Database	22123792
Thalictrum triternatum	KNApSAcK Database	22123792
Ziziphus jujuba	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protopine alkaloids. These are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protopine alkaloids

Sub Class

Not Available

Direct Parent

Protopine alkaloids

Alternative Parents

Substituents

Protopine skeleton
Benzodioxole
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzazecine alkaloid (CHEBI:16415 )
Isoquinoline alkaloids (C05189 )
a small molecule (PROTOPINE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.82 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.95	ALOGPS
logP	2.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	4.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.57 m³·mol⁻¹	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003920

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Protopine

METLIN ID

6988

PubChem Compound

4970

PDB ID

Not Available

ChEBI ID

16415

Good Scents ID

rw1836891

References

General References

Meyer A, Imming P: Benzylisoquinoline alkaloids from the papaveraceae: the heritage of Johannes Gadamer (1867-1928). J Nat Prod. 2011 Nov 28;74(11):2482-7. doi: 10.1021/np2005049. Epub 2011 Oct 26. [PubMed:22029392 ]
Paul LD, Maurer HH: Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):43-57. doi: 10.1016/s1570-0232(03)00124-7. [PubMed:12726842 ]
Wynne PM, Vine JH, Amiet RG: Protopine alkaloids in horse urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Nov 5;811(1):85-91. doi: 10.1016/j.jchromb.2004.03.077. [PubMed:15458726 ]
Jiang B, Cao K, Wang R: Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells. Eur J Pharmacol. 2004 Dec 15;506(2):93-100. doi: 10.1016/j.ejphar.2004.11.004. [PubMed:15588728 ]
Seger, C., et al. (2004). Seger, C., et al, Magn. Reson. Chem. 42, 882 (2004). Mag. Reson. Chem..

Showing NP-Card for protopine (NP0030595)

MOL for NP0030595 (protopine)

3D MOL for NP0030595 (protopine)

3D SDF for NP0030595 (protopine)

3D-SDF for NP0030595 (protopine)

PDB for NP0030595 (protopine)

3D PDB for NP0030595 (protopine)

SMILES for NP0030595 (protopine)

INCHI for NP0030595 (protopine)

Structure for NP0030595 (protopine)

3D Structure for NP0030595 (protopine)