NP-MRD: Showing NP-Card for Cepharanthine (NP0050960)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:25:42 UTC

Updated at

2022-04-27 22:25:42 UTC

NP-MRD ID

NP0050960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cepharanthine

Description

Cepharanthine belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Cepharanthine is a very strong basic compound (based on its pKa). Cepharanthine is found in Stephania cephalantha, Stephania delavayi, Stephania erecta, Stephania pierrei, Stephania rotunda , Stephania sasakii, Stephania sinica, Stephania suberosa and Stephania tetrandra . Cepharanthine was first documented in 2016 (PMID: 26703475). A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221605022D          

 47 54  0  0  1  0            999 V2000
    5.2409   -2.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -4.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052    3.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2616   -0.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -3.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802   -0.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7622    0.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997   -1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350    1.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    0.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    0.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726    0.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3002    1.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -1.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7698   -0.8841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3630    1.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2208   -3.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4718    1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -2.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595    1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807    1.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4080   -1.4258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    1.6865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -3.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437    2.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501    0.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874    1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760   -2.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0418   -0.4959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    2.7837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 22  5  2  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 23  7  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  2  0  0  0  0
 24 11  1  0  0  0  0
 24 18  2  0  0  0  0
 25 12  1  0  0  0  0
 25 19  2  0  0  0  0
 26  8  2  0  0  0  0
 26  9  1  0  0  0  0
 27 20  2  0  0  0  0
 27 24  1  0  0  0  0
 28 16  1  0  0  0  0
 28 27  1  0  0  0  0
 29 15  1  0  0  0  0
 30 10  1  0  0  0  0
 31 18  1  0  0  0  0
 32 17  1  0  0  0  0
 32 30  2  0  0  0  0
 33 20  1  0  0  0  0
 33 31  2  0  0  0  0
 34 19  1  0  0  0  0
 35 25  1  0  0  0  0
 35 29  1  0  0  0  0
 36 34  2  0  0  0  0
 37 35  2  0  0  0  0
 37 36  1  0  0  0  0
 38  1  1  0  0  0  0
 38 13  1  0  0  0  0
 38 28  1  0  0  0  0
 39  2  1  0  0  0  0
 39 14  1  0  0  0  0
 39 29  1  0  0  0  0
 40  3  1  0  0  0  0
 40 30  1  0  0  0  0
 41  4  1  0  0  0  0
 41 31  1  0  0  0  0
 42 21  1  0  0  0  0
 42 34  1  0  0  0  0
 43 21  1  0  0  0  0
 43 36  1  0  0  0  0
 44 26  1  0  0  0  0
 44 32  1  0  0  0  0
 45 33  1  0  0  0  0
 45 37  1  0  0  0  0
 28 46  1  1  0  0  0
 29 47  1  1  0  0  0
M  END

     RDKit          3D

 83 90  0  0  0  0  0  0  0  0999 V2000
    5.4509    4.5390   -1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945    4.0909   -0.2420 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2729    2.7748    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217    1.9583   -0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2280    0.6714    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640    0.1972    1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487    1.0460    1.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158    2.3383    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2281    3.3557    1.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    3.1588    0.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132    3.5178   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    3.2791   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8359    2.7045    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3567    2.3510    1.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    2.5967    1.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2776    2.4277   -0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836    0.9342   -0.4560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5359    0.1036    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7155    0.2393    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240   -0.4045    2.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -1.1732    3.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -1.3102    2.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617   -0.6894    1.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891   -0.7661    0.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070   -1.2047   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258   -1.3227    0.6635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197   -1.7821   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -2.1332   -1.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027   -2.0316   -2.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2802   -1.5595   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.4813   -2.1641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4985   -1.8308   -3.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685   -2.7199   -2.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -3.7810   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7991   -3.4072    0.1601 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8548   -4.2309    0.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.9953    0.2845 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2750   -1.3028    1.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.1737    3.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -2.8408    4.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804   -1.9103    4.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8649    1.0247    0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8852    1.0713   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853    0.7669   -1.2090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055    1.2558   -2.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4381    4.3021   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928    4.1773   -2.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    5.6515   -1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1512    2.2966   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0558   -0.0135    0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    0.7453    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674    4.0198   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    3.6495   -1.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8299    1.8696    2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    2.2664    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262    2.7540    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7243    2.9412   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6275    0.6390   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8674   -0.2908    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0408   -1.0652    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258   -2.3112   -3.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.3084   -4.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693   -1.4700   -3.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823   -2.9198   -3.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -1.9920   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -3.2761   -2.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -3.9381   -1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758   -4.7394   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9786   -3.6709    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4291   -5.0472    0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3548   -4.7930    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -1.5873   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3660   -1.6270    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0105   -1.7184    2.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -3.7973    3.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3481   -3.0086    5.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0261    1.9826    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8184    0.4607    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6574    0.3721   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2824    2.0901   -0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6339    2.3434   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4875    0.8601   -3.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    0.8008   -3.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
 37 38  1  0
 38  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 16  1  0
 16 17  1  0
 17 44  1  0
 44 45  1  0
 44 43  1  0
 43 42  1  0
 42 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 39  1  0
 39 40  1  0
 40 41  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 30  2  0
 30 31  1  0
 31 32  1  0
 30 29  1  0
 29 28  2  0
 28 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 28 27  1  0
 27 26  2  0
 23 18  2  0
 13 14  1  0
 14 15  2  0
  8  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
 35 37  1  0
 27 37  1  0
  5  6  1  0
 15 10  1  0
 18 17  1  0
 18 19  1  0
 41 21  1  0
 26 25  1  0
 37 72  1  6
 38 73  1  0
 38 74  1  0
  7 51  1  0
 11 52  1  0
 12 53  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  6
 45 81  1  0
 45 82  1  0
 45 83  1  0
 43 79  1  0
 43 80  1  0
 42 77  1  0
 42 78  1  0
 20 59  1  0
 40 75  1  0
 40 76  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
 29 61  1  0
 33 65  1  0
 33 66  1  0
 34 67  1  0
 34 68  1  0
 36 69  1  0
 36 70  1  0
 36 71  1  0
 26 60  1  0
 14 54  1  0
 15 55  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  4 49  1  0
  5 50  1  0
M  END


  Mrv1572004221605022D          

 47 54  0  0  1  0            999 V2000
    5.2409   -2.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6930   -4.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052    3.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2616   -0.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876   -3.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802   -0.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7622    0.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997   -1.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7765   -1.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350    1.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    0.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    0.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726    0.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713   -2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877    0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3002    1.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -1.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7698   -0.8841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3630    1.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2208   -3.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4718    1.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -2.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595    1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807    1.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4080   -1.4258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408    1.6865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -3.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437    2.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501    0.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874    1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760   -2.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0418   -0.4959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    2.7837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 22  5  2  0  0  0  0
 22  6  1  0  0  0  0
 22 15  1  0  0  0  0
 23  7  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  2  0  0  0  0
 24 11  1  0  0  0  0
 24 18  2  0  0  0  0
 25 12  1  0  0  0  0
 25 19  2  0  0  0  0
 26  8  2  0  0  0  0
 26  9  1  0  0  0  0
 27 20  2  0  0  0  0
 27 24  1  0  0  0  0
 28 16  1  0  0  0  0
 28 27  1  0  0  0  0
 29 15  1  0  0  0  0
 30 10  1  0  0  0  0
 31 18  1  0  0  0  0
 32 17  1  0  0  0  0
 32 30  2  0  0  0  0
 33 20  1  0  0  0  0
 33 31  2  0  0  0  0
 34 19  1  0  0  0  0
 35 25  1  0  0  0  0
 35 29  1  0  0  0  0
 36 34  2  0  0  0  0
 37 35  2  0  0  0  0
 37 36  1  0  0  0  0
 38  1  1  0  0  0  0
 38 13  1  0  0  0  0
 38 28  1  0  0  0  0
 39  2  1  0  0  0  0
 39 14  1  0  0  0  0
 39 29  1  0  0  0  0
 40  3  1  0  0  0  0
 40 30  1  0  0  0  0
 41  4  1  0  0  0  0
 41 31  1  0  0  0  0
 42 21  1  0  0  0  0
 42 34  1  0  0  0  0
 43 21  1  0  0  0  0
 43 36  1  0  0  0  0
 44 26  1  0  0  0  0
 44 32  1  0  0  0  0
 45 33  1  0  0  0  0
 45 37  1  0  0  0  0
 28 46  1  1  0  0  0
 29 47  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC3=CC(OC4=CC=C(C[C@]5([H])N(C)CCC6=CC7=C(OCO7)C(OC7=C(OC)C=C(CCN1C)C2=C7)=C56)C=C4)=C(OC)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1

> <INCHI_KEY>
YVPXVXANRNDGTA-WDYNHAJCSA-N

> <FORMULA>
C37H38N2O6

> <MOLECULAR_WEIGHT>
606.719

> <EXACT_MASS>
606.272986952

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
65.7914965808383

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2¹⁶,¹⁹.1³,¹⁰.1²¹,²⁵.0⁴,⁸.0³¹,³⁵.0¹⁴,³⁹]nonatriaconta-1(33),3(39),4(8),9,16,18,21,23,25(36),31,34,37-dodecaene

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
6.416838633666666

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
8.316392377787107

> <JCHEM_POLAR_SURFACE_AREA>
61.860000000000014

> <JCHEM_REFRACTIVITY>
172.95509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cepharanthine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       9.783  -4.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.028   3.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.160  -8.453   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.716   5.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.048  -0.270   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.464  -0.534   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.801  -5.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.355  -1.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.264  -2.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.577  -6.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.910  -0.699   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.289   0.853   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.573  -2.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.922   1.521   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.134   2.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.801  -2.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.183  -3.524   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.265   1.901   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.370   0.839   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.543   1.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.149   1.981   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.696   0.548   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.666  -4.038   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.804   0.389   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.294   1.907   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.178  -2.760   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.303  -0.053   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.904  -1.650   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.544   3.673   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.145  -5.974   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.214   3.047   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.890  -4.429   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.662   2.802   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.712   1.459   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.218   3.455   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.871   2.991   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.806   4.042   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      10.095  -2.662   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       1.383   3.148   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0       2.937  -6.929   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      10.722   4.501   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.120   0.835   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       8.377   3.314   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.382  -3.841   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       7.525   4.107   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0       7.545  -0.926   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.318   5.196   0.000  0.00  0.00           H+0
CONECT    1   38                                                            
CONECT    2   39                                                            
CONECT    3   40                                                            
CONECT    4   41                                                            
CONECT    5    8   22                                                       
CONECT    6    9   22                                                       
CONECT    7   10   23                                                       
CONECT    8    5   26                                                       
CONECT    9    6   26                                                       
CONECT   10    7   30                                                       
CONECT   11   13   24                                                       
CONECT   12   14   25                                                       
CONECT   13   11   38                                                       
CONECT   14   12   39                                                       
CONECT   15   22   29                                                       
CONECT   16   23   28                                                       
CONECT   17   23   32                                                       
CONECT   18   24   31                                                       
CONECT   19   25   34                                                       
CONECT   20   27   33                                                       
CONECT   21   42   43                                                       
CONECT   22    5    6   15                                                  
CONECT   23    7   16   17                                                  
CONECT   24   11   18   27                                                  
CONECT   25   12   19   35                                                  
CONECT   26    8    9   44                                                  
CONECT   27   20   24   28                                                  
CONECT   28   16   27   38   46                                             
CONECT   29   15   35   39   47                                             
CONECT   30   10   32   40                                                  
CONECT   31   18   33   41                                                  
CONECT   32   17   30   44                                                  
CONECT   33   20   31   45                                                  
CONECT   34   19   36   42                                                  
CONECT   35   25   29   37                                                  
CONECT   36   34   37   43                                                  
CONECT   37   35   36   45                                                  
CONECT   38    1   13   28                                                  
CONECT   39    2   14   29                                                  
CONECT   40    3   30                                                       
CONECT   41    4   31                                                       
CONECT   42   21   34                                                       
CONECT   43   21   36                                                       
CONECT   44   26   32                                                       
CONECT   45   33   37                                                       
CONECT   46   28                                                            
CONECT   47   29                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Value	Source
(+)-Cepharanthine	ChEBI
6',12'-Dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan	ChEBI
Cepharanthin	MeSH

Chemical Formula

C₃₇H₃₈N₂O₆

Average Mass

606.7190 Da

Monoisotopic Mass

606.27299 Da

IUPAC Name

(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2¹⁶,¹⁹.1³,¹⁰.1²¹,²⁵.0⁴,⁸.0³¹,³⁵.0¹⁴,³⁹]nonatriaconta-1(33),3(39),4(8),9,16,18,21,23,25(36),31,34,37-dodecaene

Traditional Name

cepharanthine

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=CC(OC4=CC=C(C[C@]5([H])N(C)CCC6=CC7=C(OCO7)C(OC7=C(OC)C=C(CCN1C)C2=C7)=C56)C=C4)=C(OC)C=C3

InChI Identifier

InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1

InChI Key

YVPXVXANRNDGTA-WDYNHAJCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Stephania cephalantha	Plant	KNApSAcK
Stephania delavayi	Plant	KNApSAcK
Stephania erecta	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Stephania rotunda	Plant	KNApSAcK
Stephania sasakii	Plant	KNApSAcK
Stephania sinica	LOTUS Database	35616633
Stephania suberosa	LOTUS Database	35616633
Stephania tetrandra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Diaryl ether
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:3546 )
Isoquinoline alkaloids (C09391 )

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	5.31	ALOGPS
logP	6.42	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	172.96 m³·mol⁻¹	ChemAxon
Polarizability	65.79 Å³	ChemAxon
Number of Rings	8	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

C00001836

Chemspider ID

Not Available

KEGG Compound ID

C09391

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cepharanthine

METLIN ID

Not Available

PubChem Compound

10206

PDB ID

Not Available

ChEBI ID

3546

Good Scents ID

Not Available

References

General References

Li CW, Menconi F, Osman R, Mezei M, Jacobson EM, Concepcion E, David CS, Kastrinsky DB, Ohlmeyer M, Tomer Y: Identifying a Small Molecule Blocking Antigen Presentation in Autoimmune Thyroiditis. J Biol Chem. 2016 Feb 19;291(8):4079-90. doi: 10.1074/jbc.M115.694687. Epub 2015 Dec 24. [PubMed:26703475 ]

Showing NP-Card for Cepharanthine (NP0050960)

MOL for NP0050960 (Cepharanthine)

3D MOL for NP0050960 (Cepharanthine)

3D SDF for NP0050960 (Cepharanthine)

3D-SDF for NP0050960 (Cepharanthine)

PDB for NP0050960 (Cepharanthine)

3D PDB for NP0050960 (Cepharanthine)

SMILES for NP0050960 (Cepharanthine)

INCHI for NP0050960 (Cepharanthine)

Structure for NP0050960 (Cepharanthine)

3D Structure for NP0050960 (Cepharanthine)