NP-MRD: Showing NP-Card for (-)-Cycleanine (NP0067788)

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Record Information

Version

1.0

Created at

2022-04-28 12:38:15 UTC

Updated at

2022-04-28 12:38:15 UTC

NP-MRD ID

NP0067788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cycleanine

Description

Cycleanine belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. (-)-Cycleanine is found in Anisocycla jollyana, Anisocyla jollyana, Chondrodendron tomentosum, Cissampelos capensis, Cissampelos pareira L. , Cyclea hypoglauca Diels, Cyclea peltata , Cyclea sutchuenensis Gagnep., Cyclea sutchuensis, Cyclea tonkinensis Gagnep., Epinetrum villosum (Exell.) Troupin, Heracleum wallichii, Limaciopsis loangensis Engl., Sinomenium diversifolium Diels, Stephania brachyandra Diels, Stephania cephalantha, Stephania cepharantha Hayata , Stephania delavayi Diels, Stephania dicentrinifera H.S.Lo & M.Yang, Stephania elegans, Stephania epigaea H.S.Lo, Stephania epigeae H.S.Lo., Stephania glabra Miers , Stephania hainanensis H.S.Lo & Y., Stephania hernandifolia (Willd.) Walp. , Stephania kwangsiensis H.S.Lo, Stephania longa L. , Stephania micrantha H.S.Lo, Stephania pierii, Stephania pierrei, Stephania pierrei Diels(=S.erecta Craib) , Stephania rotunda Lour. , Stephania sinica Diels, Stephania sp. , Stephania succinifera H.S.Lo, Stephania tetrandra S.Moore and Synclisia scabrida Miers . It was first documented in 2016 (PMID: 27270992). Based on a literature review a significant number of articles have been published on Cycleanine (PMID: 33257443) (PMID: 32456907) (PMID: 29588214) (PMID: 29126362).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214382D          

 46 52  0  0  1  0            999 V2000
   11.5514    2.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3700    2.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7658    0.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9704    0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3525    1.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7489    0.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0587    0.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4838    0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6675    0.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7818   -0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5188   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6936    0.2842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.9840   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3571    0.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1510    0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
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 45 46  1  0  0  0  0
M  END

     RDKit          3D

 88 94  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282214382D          

 46 52  0  0  1  0            999 V2000
   11.5514    2.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3700    2.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7658    0.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9704    0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3525    1.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7489    0.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0587    0.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4838    0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6675    0.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7818   -0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5188   -0.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6936    0.2842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4308   -0.5112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6290   -0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0584   -0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2785    0.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0972    0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961    1.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    2.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8827    2.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915    2.6950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976    2.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729    3.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    3.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8997    2.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898    2.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8668    3.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6945    3.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2726    3.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1298    3.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550    2.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2178    3.5676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0195    3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5902    3.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6567    4.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9811    2.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1648    2.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919   -1.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7757   -0.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9840   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3571    0.3614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1510    0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  1 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 36 39  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  2  0  0  0  0
 30 41  1  0  0  0  0
 16 42  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  1  0  0  0  0
  4 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@@H](CC4=CC=C(OC5=C(OC)C(OC)=CC6=C5[C@@H](CC5=CC=C(OC3=C1OC)C=C5)N(C)CC6)C=C4)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1

> <INCHI_KEY>
ANOXEUSGZWSCQL-LOYHVIPDSA-N

> <FORMULA>
C38H42N2O6

> <MOLECULAR_WEIGHT>
622.762

> <EXACT_MASS>
622.30428708

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
68.30105977692308

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,26R)-4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2^{13,16}.1^{3,7}.1^{18,22}.0^{11,36}.0^{26,33}]hexatriaconta-1(30),3,5,7(36),13,15,18,20,22(33),28,31,34-dodecaene

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
6.478262634666667

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
8.208306246510785

> <JCHEM_POLAR_SURFACE_AREA>
61.860000000000014

> <JCHEM_REFRACTIVITY>
180.1145999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,26R)-4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2^{13,16}.1^{3,7}.1^{18,22}.0^{11,36}.0^{26,33}]hexatriaconta-1(30),3,5,7(36),13,15,18,20,22(33),28,31,34-dodecaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      21.563   3.986   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.091   4.377   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.203   3.262   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.830   1.749   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.345   1.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.191   2.404   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      20.065   1.259   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.776   0.300   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.703   1.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.179   1.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.635  -0.358   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.714  -1.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.259  -1.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.035  -0.033   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.495   0.531   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      12.004  -0.954   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      10.508  -1.327   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.442  -0.205   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.853   1.329   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.382   1.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.753   3.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.599   4.367   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.114   3.957   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.741   2.443   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.011   5.031   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.529   4.612   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.963   5.863   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.848   6.926   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.879   4.447   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.168   5.405   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.685   6.898   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.230   7.206   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.309   6.063   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.909   5.738   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.449   5.175   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      20.940   6.659   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      22.436   7.032   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.502   5.910   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.893   7.789   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.765   4.605   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.241   4.288   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.051  -2.083   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      21.981  -0.158   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      20.504  -0.591   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      24.933   0.675   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      26.415   1.093   0.000  0.00  0.00           C+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   45                                                  
CONECT    5    4    6   43                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   42                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22   28                                                       
CONECT   28   27                                                            
CONECT   29   21   30                                                       
CONECT   30   29   31   41                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34    1   36                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37    2                                                       
CONECT   39   36                                                            
CONECT   40   33   41                                                       
CONECT   41   40   30                                                       
CONECT   42   16                                                            
CONECT   43    5   44                                                       
CONECT   44   43                                                            
CONECT   45    4   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Value	Source
Isocycleanine	MeSH

Chemical Formula

C₃₈H₄₂N₂O₆

Average Mass

622.7620 Da

Monoisotopic Mass

622.30429 Da

IUPAC Name

(11R,26R)-4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2^{13,16}.1^{3,7}.1^{18,22}.0^{11,36}.0^{26,33}]hexatriaconta-1(30),3,5,7(36),13,15,18,20,22(33),28,31,34-dodecaene

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@@H](CC4=CC=C(OC5=C(OC)C(OC)=CC6=C5[C@@H](CC5=CC=C(OC3=C1OC)C=C5)N(C)CC6)C=C4)N(C)CC2

InChI Identifier

InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1

InChI Key

ANOXEUSGZWSCQL-LOYHVIPDSA-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
Anisocycla jollyana	Plant	KNApSAcK
Anisocyla jollyana	Plant	KNApSAcK
Chondodendron tomentosum	LOTUS Database	35616633
Cissampelos capensis	LOTUS Database	35616633
Cissampelos pareira	Plant	KNApSAcK
Cyclea hypoglauca Diels	Plant	KNApSAcK
Cyclea peltata	Plant	KNApSAcK
Cyclea sutchuenensis Gagnep.	Plant	KNApSAcK
Cyclea sutchuensis	Plant	KNApSAcK
Cyclea tonkinensis Gagnep.	Plant	KNApSAcK
Epinetrum villosum (Exell.) Troupin	Plant	KNApSAcK
Heracleum wallichii	Plant	KNApSAcK
Limaciopsis loangensis Engl.	Plant	KNApSAcK
Sinomenium diversifolium Diels	Plant	KNApSAcK
Stephania brachyandra Diels	Plant	KNApSAcK
Stephania cephalantha	LOTUS Database	35616633
Stephania cepharantha Hayata	Plant	KNApSAcK
Stephania delavayi	Plant	KNApSAcK
Stephania dicentrinifera H.S.Lo & M.Yang	Plant	KNApSAcK
Stephania elegans	LOTUS Database	35616633
Stephania epigaea	Plant	KNApSAcK
Stephania epigeae H.S.Lo.	Plant	KNApSAcK
Stephania glabra Miers	Plant	KNApSAcK
Stephania hainanensis H.S.Lo & Y.	Plant	KNApSAcK
Stephania hernandifolia	Plant	KNApSAcK
Stephania kwangsiensis H.S.Lo	Plant	KNApSAcK
Stephania longa L.	Plant	KNApSAcK
Stephania micrantha H.S.Lo	Plant	KNApSAcK
Stephania pierii	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Stephania pierrei Diels(=S.erecta Craib)	Plant	KNApSAcK
Stephania rotunda	Plant	KNApSAcK
Stephania sinica Diels	Plant	KNApSAcK
Stephania sp.	Plant	KNApSAcK
Stephania succinifera H.S.Lo	Plant	KNApSAcK
Stephania tetrandra	Plant	KNApSAcK
Synclisia scabrida Miers	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:81051 )

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	5.58	ALOGPS
logP	6.48	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	8.21	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	4	ChemAxon
Refractivity	180.11 m³·mol⁻¹	ChemAxon
Polarizability	68.3 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025604

Chemspider ID

108295

KEGG Compound ID

C17387

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cycleanine

METLIN ID

Not Available

PubChem Compound

121313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uche FI, Guo X, Okokon J, Ullah I, Horrocks P, Boateng J, Huang C, Li WW: In Vivo Efficacy and Metabolism of the Antimalarial Cycleanine and Improved In Vitro Antiplasmodial Activity of Semisynthetic Analogues. Antimicrob Agents Chemother. 2021 Jan 20;65(2). pii: AAC.01995-20. doi: 10.1128/AAC.01995-20. Print 2021 Jan 20. [PubMed:33257443 ]
Yang L, Zhao J, Wang J, Han G, Liu B, Zhang W, Fu Y, Han MY, Wang Z, Zhang Z: An azacyclo-localizing fluorescent probe for the specific labeling of lysosome and autolysosome. Talanta. 2020 Aug 15;216:120941. doi: 10.1016/j.talanta.2020.120941. Epub 2020 Mar 23. [PubMed:32456907 ]
Uche FI, McCullagh J, Claridge TWD, Richardson A, Li WW: Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells. Bioorg Med Chem Lett. 2018 May 15;28(9):1652-1656. doi: 10.1016/j.bmcl.2018.03.038. Epub 2018 Mar 16. [PubMed:29588214 ]
Bala M, Kumar S, Pratap K, Verma PK, Padwad Y, Singh B: Bioactive isoquinoline alkaloids from Cissampelos pareira (dagger). Nat Prod Res. 2019 Mar;33(5):622-627. doi: 10.1080/14786419.2017.1402319. Epub 2017 Nov 10. [PubMed:29126362 ]
Uche FI, Drijfhout FP, McCullagh J, Richardson A, Li WW: Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids from Triclisia subcordata. Phytother Res. 2016 Sep;30(9):1533-9. doi: 10.1002/ptr.5660. Epub 2016 Jun 8. [PubMed:27270992 ]

Showing NP-Card for (-)-Cycleanine (NP0067788)

MOL for NP0067788 ((-)-Cycleanine)

3D MOL for NP0067788 ((-)-Cycleanine)

3D SDF for NP0067788 ((-)-Cycleanine)

3D-SDF for NP0067788 ((-)-Cycleanine)

PDB for NP0067788 ((-)-Cycleanine)

3D PDB for NP0067788 ((-)-Cycleanine)

SMILES for NP0067788 ((-)-Cycleanine)

INCHI for NP0067788 ((-)-Cycleanine)

Structure for NP0067788 ((-)-Cycleanine)

3D Structure for NP0067788 ((-)-Cycleanine)