NP-MRD: Showing NP-Card for 2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium (NP0264923)

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Record Information

Version

2.0

Created at

2022-09-08 08:43:12 UTC

Updated at

2022-09-08 08:43:13 UTC

NP-MRD ID

NP0264923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium

Description

Phellodendrine, also known as ob-5 compound, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Phellodendrine is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium is found in Phellodendron amurense, Phellodendron chinense and Xylopia parviflora. Phellodendrine is an alkaloid isolated originally from Phellodendron amurense (Rutaceae).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502172D          

 25 28  0  0  0  0            999 V2000
    2.1265   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9071    1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2278   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    6.4978   -0.5368   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7648    0.6573   -0.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4424    0.8142   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041   -0.2572    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -0.0764    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8216    1.1635    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310    2.2034   -0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682    2.0490   -0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015    3.1216   -1.2472 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    1.2398    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    0.0572   -0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7117    0.2281   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    1.3975   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5768    1.6798   -0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    2.8822   -1.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4440    0.7479   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8187    1.0279   -0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7196    0.0909    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967   -0.4259    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.6655    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0902   -1.9323    0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.6674    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1904   -1.1863    0.2671 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.2564   -2.1844   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -1.1216    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8509   -0.5673    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3814   -0.5999   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8845   -1.4486   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553   -1.2275    0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336    3.1486   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5712    2.9557   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3159    1.0443    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.1771    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    0.1389   -1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506    2.1311   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813    3.5502   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7611    0.3843   -0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4802   -0.9007   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5502   -0.0219    1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6768   -1.1749    0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046   -2.3087    1.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0910   -2.6645   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -0.9259    2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -2.6040    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1466   -1.9073   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504   -2.1477   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4583   -3.1999   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -2.1088    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849   -1.0288    1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 25  5  1  0
 23 11  1  0
 20 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  6
 13 35  1  0
 15 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
  7 30  1  0
  9 31  1  0
M  CHG  1  23   1
M  END


  Mrv1533004201502172D          

 25 28  0  0  0  0            999 V2000
    2.1265   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0168   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.2664    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9071    1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172    0.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2278   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4472   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9071   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0264923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(CC3C4=CC(O)=C(OC)C=C4CC[N+]3(C)C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-21-5-4-12-8-19(24-2)18(23)10-15(12)16(21)6-13-7-17(22)20(25-3)9-14(13)11-21/h7-10,16H,4-6,11H2,1-3H3,(H-,22,23)/p+1

> <INCHI_KEY>
RBBVPNQTBKHOEQ-UHFFFAOYSA-O

> <FORMULA>
C20H24NO4

> <MOLECULAR_WEIGHT>
342.414

> <EXACT_MASS>
342.169984677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.1792170835856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,11-dihydroxy-3,10-dimethoxy-6-methyl-5,6,7,8,12b,13-hexahydro-6-azatetraphen-6-ium

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
-1.3061500081384116

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.133112828025352

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5309159801466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591579214134529

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
108.3045

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5H-6-azatetraphen-6-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.969  -2.122   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.978  -0.958   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      11.531   0.497   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      11.027   1.952   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.084  -2.122   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.092  -0.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.067  -4.450   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.986  -3.868   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
OB-5 compound	MeSH
Phallodendrin	MeSH

Chemical Formula

C₂₀H₂₄NO₄

Average Mass

342.4140 Da

Monoisotopic Mass

342.16998 Da

IUPAC Name

2,11-dihydroxy-3,10-dimethoxy-6-methyl-5,6,7,8,12b,13-hexahydro-6-azatetraphen-6-ium

Traditional Name

2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5H-6-azatetraphen-6-ium

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CC3C4=CC(O)=C(OC)C=C4CC[N+]3(C)C2)C=C1O

InChI Identifier

InChI=1S/C20H23NO4/c1-21-5-4-12-8-19(24-2)18(23)10-15(12)16(21)6-13-7-17(22)20(25-3)9-14(13)11-21/h7-10,16H,4-6,11H2,1-3H3,(H-,22,23)/p+1

InChI Key

RBBVPNQTBKHOEQ-UHFFFAOYSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phellodendron amurense	LOTUS Database	35616633
Phellodendron chinense	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.75	ALOGPS
logP	-1.3	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.3 m³·mol⁻¹	ChemAxon
Polarizability	38.18 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phellodendrine

METLIN ID

Not Available

PubChem Compound

12305144

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium (NP0264923)

MOL for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

3D MOL for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

3D SDF for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

3D-SDF for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

PDB for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

3D PDB for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

SMILES for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

INCHI for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

Structure for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)

3D Structure for NP0264923 (2,11-dihydroxy-3,10-dimethoxy-6-methyl-7,8,12b,13-tetrahydro-5h-6-azatetraphen-6-ium)