NP-MRD: Showing NP-Card for sinomenine (NP0028264)

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Record Information

Version

2.0

Created at

2021-06-19 20:12:19 UTC

Updated at

2021-08-20 00:00:12 UTC

NP-MRD ID

NP0028264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sinomenine

Provided By

JEOL Database JEOL Logo

Description

sinomenine is found in Menispermum dauricum, Sinomenium acutum, Stephania cepharantha and Stephania cepharantha Hayata . sinomenine was first documented in 2005 (Bao, G.-H., et al.). Based on a literature review very few articles have been published on (1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]Heptadeca-2(7),3,5,11-tetraen-13-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122123D          

 47 50  0  0  0  0            999 V2000
   -4.8313   -0.2897   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.2598   -2.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.5217   -2.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823    0.1064   -2.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    0.8377   -2.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9529   -0.0842   -2.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7634   -1.0041   -1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1780   -0.3328    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -1.0781    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363   -0.5272    2.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2464    1.4728    3.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1351    2.8452    1.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9705    2.6383   -1.3772 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2391    1.7744   -1.4159 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1779    0.7530   -2.4687 N   0  0  1  0  0  0  0  0  0  0  0  0
    3.4103   -0.0287   -2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
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 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -4.8313   -0.2897   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.2598   -2.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.5217   -2.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823    0.1064   -2.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192122123D          

 47 50  0  0  0  0            999 V2000
   -4.8313   -0.2897   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.2598   -2.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 33  1  0  0  0  0
 10 34  1  0  0  0  0
  6 30  1  6  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
  4 28  1  0  0  0  0
 15 38  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1[C@]13C([H])([H])C(=O)C(OC([H])([H])[H])=C([H])[C@]1([H])[C@@]([H])(N(C([H])([H])[H])C([H])([H])C3([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1

> <INCHI_KEY>
INYYVPJSBIVGPH-QHRIQVFBSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.396

> <EXACT_MASS>
329.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19188569545185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.4476778569943256

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.838554552671848

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.832212233116003

> <JCHEM_PKA_STRONGEST_BASIC>
8.271200100287679

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
92.99739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -4.8313   -0.2897   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.2598   -2.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.5217   -2.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823    0.1064   -2.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    0.8377   -2.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9529   -0.0842   -2.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7634   -1.0041   -1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1780   -0.3328    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -1.0781    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363   -0.5272    2.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799    0.7877    2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464    1.4728    3.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254    0.7469    4.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    1.5302    1.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351    2.8452    1.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287    0.9867   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207    1.7848   -1.3451 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9705    2.6383   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.7744   -1.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.7530   -2.4687 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.0287   -2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    2.6812   -1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362    1.8650   -1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005    2.3268   -1.2237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4202   -1.2061   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -0.3160   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5231    0.5536   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502   -0.8193   -3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277    1.4353   -3.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9961   -0.7308   -3.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -1.4864   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806   -1.8177   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197   -2.1020    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -1.1434    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    0.4277    5.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7318    1.4192    5.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1053    4.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    2.9794    2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0198    3.3108   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622    3.2832   -2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210    1.3207   -0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    2.4413   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -0.5446   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2635    0.6225   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3717   -0.7731   -3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773    3.2158   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699    3.4598   -0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  5  4  1  0
 17 22  1  6
 22 23  1  0
 23  3  1  0
  3  4  2  0
 11 14  2  0
 11 12  1  0
  8  7  1  0
 14 15  1  0
 16 17  1  0
 12 13  1  0
  5  6  1  0
 23 24  2  0
  6  7  1  0
  3  2  1  0
  5 17  1  0
  2  1  1  0
  9 10  2  0
 17 18  1  0
 10 11  1  0
  6 20  1  0
  8 16  2  0
 20 19  1  0
 18 19  1  0
 14 16  1  0
  5 29  1  6
 20 21  1  0
  9 33  1  0
 10 34  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
 22 46  1  0
 22 47  1  0
  4 28  1  0
 15 38  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  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      -4.831  -0.290  -1.498  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.886  -0.260  -2.563  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.768   0.522  -2.322  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.582   0.106  -2.793  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   0.838  -2.581  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.953  -0.084  -2.434  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.763  -1.004  -1.210  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.178  -0.333   0.013  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.149  -1.078   1.206  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.336  -0.527   2.391  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.780   0.788   2.400  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.246   1.473   3.495  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.325   0.747   4.717  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.756   1.530   1.205  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.135   2.845   1.279  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.329   0.987  -0.018  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.321   1.785  -1.345  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.971   2.638  -1.377  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.239   1.774  -1.416  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.178   0.753  -2.469  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.410  -0.029  -2.513  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.559   2.681  -1.570  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.836   1.865  -1.634  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.901   2.327  -1.224  0.00  0.00           O+0
HETATM   25  H   UNK     0      -5.420  -1.206  -1.604  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.346  -0.316  -0.517  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.523   0.554  -1.576  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.550  -0.819  -3.363  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.128   1.435  -3.495  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.996  -0.731  -3.322  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.710  -1.486  -0.943  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.081  -1.818  -1.490  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.520  -2.102   1.216  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.333  -1.143   3.283  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.333   0.428   5.050  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.732   1.419   5.479  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.007  -0.105   4.627  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.428   2.979   2.202  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.020   3.311  -0.512  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.962   3.283  -2.267  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.421   1.321  -0.434  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.090   2.441  -1.607  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.619  -0.545  -1.570  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.263   0.623  -2.734  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.372  -0.773  -3.316  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.477   3.216  -2.526  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.670   3.460  -0.813  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3   23    4    2                                                  
CONECT    4    5    3   28                                                  
CONECT    5    4    6   17   29                                             
CONECT    6    5    7   20   30                                             
CONECT    7    8    6   31   32                                             
CONECT    8    9    7   16                                                  
CONECT    9    8   10   33                                                  
CONECT   10    9   11   34                                                  
CONECT   11   14   12   10                                                  
CONECT   12   11   13                                                       
CONECT   13   12   35   36   37                                             
CONECT   14   11   15   16                                                  
CONECT   15   14   38                                                       
CONECT   16   17    8   14                                                  
CONECT   17   22   16    5   18                                             
CONECT   18   17   19   39   40                                             
CONECT   19   20   18   41   42                                             
CONECT   20    6   19   21                                                  
CONECT   21   20   43   44   45                                             
CONECT   22   17   23   46   47                                             
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   15                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   21                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

RDKit          3D

47 50  0  0  0  0  0  0  0  0999 V2000
   -4.8313   -0.2897   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -0.2598   -2.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.5217   -2.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823    0.1064   -2.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    0.8377   -2.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9529   -0.0842   -2.4342 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7634   -1.0041   -1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1780   -0.3328    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -1.0781    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363   -0.5272    2.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799    0.7877    2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464    1.4728    3.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254    0.7469    4.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561    1.5302    1.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351    2.8452    1.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287    0.9867   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207    1.7848   -1.3451 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9705    2.6383   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.7744   -1.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779    0.7530   -2.4687 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -0.0287   -2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    2.6812   -1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362    1.8650   -1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005    2.3268   -1.2237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4202   -1.2061   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -0.3160   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5231    0.5536   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502   -0.8193   -3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277    1.4353   -3.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9961   -0.7308   -3.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -1.4864   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806   -1.8177   -1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197   -2.1020    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -1.1434    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    0.4277    5.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7318    1.4192    5.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1053    4.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    2.9794    2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0198    3.3108   -0.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622    3.2832   -2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210    1.3207   -0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    2.4413   -1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -0.5446   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2635    0.6225   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3717   -0.7731   -3.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773    3.2158   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699    3.4598   -0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  5  4  1  0
 17 22  1  6
 22 23  1  0
 23  3  1  0
  3  4  2  0
 11 14  2  0
 11 12  1  0
  8  7  1  0
 14 15  1  0
 16 17  1  0
 12 13  1  0
  5  6  1  0
 23 24  2  0
  6  7  1  0
  3  2  1  0
  5 17  1  0
  2  1  1  0
  9 10  2  0
 17 18  1  0
 10 11  1  0
  6 20  1  0
  8 16  2  0
 20 19  1  0
 18 19  1  0
 14 16  1  0
  5 29  1  6
 20 21  1  0
  9 33  1  0
 10 34  1  0
  6 30  1  6
  7 31  1  0
  7 32  1  0
 22 46  1  0
 22 47  1  0
  4 28  1  0
 15 38  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Cocculine	MeSH
Cucoline	MeSH
Cuculine	MeSH
Cucoline hydrochloride	MeSH
Cucoline, hydrochloride	MeSH
Sinomenin hydrochloride	MeSH
Sinomenine hydrochloride	MeSH
Kukoline	MeSH
4-Hydroxy-3,7-dimethoxy-17-methylmorphin-7-en- 6-one	MeSH
Sinomenine a bismethyliodide	MeSH

Chemical Formula

C₁₉H₂₃NO₄

Average Mass

329.3960 Da

Monoisotopic Mass

329.16271 Da

IUPAC Name

(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one

Traditional Name

(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5,11-tetraen-13-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C2=C1[C@]13C([H])([H])C(=O)C(OC([H])([H])[H])=C([H])[C@]1([H])[C@@]([H])(N(C([H])([H])[H])C([H])([H])C3([H])[H])C2([H])[H]

InChI Identifier

InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1

InChI Key

INYYVPJSBIVGPH-QHRIQVFBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Cocculus laurifolius DC.	KNApSAcK Database	22123792
Menispermum dahyricum	KNApSAcK Database	22123792
Menispermum dauricum	LOTUS Database	35616633
Menispermum dauricum DC.	KNApSAcK Database	22123792
Sinomenium acutum	JEOL database	Bao, G.-H., et al, J. Nat. prod. 68, 1128 (2005)
Stephania cephalantha	Plant	KNApSAcK
Stephania cepharantha	KNApSAcK Database	22123792
Stephania cepharantha Hayata	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	162.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	513.00 to 514.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10710 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.245 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.89	ALOGPS
logP	1.45	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93 m³·mol⁻¹	ChemAxon
Polarizability	35.19 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001918

Chemspider ID

10179905

KEGG Compound ID

C09643

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1282951

References

General References

Bao, G.-H., et al. (2005). Bao, G.-H., et al, J. Nat. prod. 68, 1128 (2005). J. Nat. Prod..

Showing NP-Card for sinomenine (NP0028264)

MOL for NP0028264 (sinomenine)

3D MOL for NP0028264 (sinomenine)

3D SDF for NP0028264 (sinomenine)

3D-SDF for NP0028264 (sinomenine)

PDB for NP0028264 (sinomenine)

3D PDB for NP0028264 (sinomenine)

SMILES for NP0028264 (sinomenine)

INCHI for NP0028264 (sinomenine)

Structure for NP0028264 (sinomenine)

3D Structure for NP0028264 (sinomenine)