NP-MRD: Showing NP-Card for (1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol (NP0222673)

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Record Information

Version

2.0

Created at

2022-09-06 00:34:11 UTC

Updated at

2022-09-06 00:34:11 UTC

NP-MRD ID

NP0222673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol

Description

Baluchistine 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. (1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol is found in Berberis aquifolium and Berberis lycium. (1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol was first documented in 1996 (PMID: 8941945). Based on a literature review very few articles have been published on Baluchistine (PMID: 11914967).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202342D          

 44 50  0  0  1  0            999 V2000
   -1.3704    1.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5847    0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -0.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546   -0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    0.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458    1.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8008    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921    0.9806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8543   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -1.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  6 36  1  0  0  0  0
 36 37  1  1  0  0  0
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  5 40  1  0  0  0  0
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 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 17 44  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062202342D          

 44 50  0  0  1  0            999 V2000
   -1.3704    1.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    1.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9546   -0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    0.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458    1.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8008    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921    0.9806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    1.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -1.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287   -0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454    0.5850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1214    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3955   -0.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7013   -1.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4396   -1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0197   -2.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8083   -2.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9888   -1.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3090   -3.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -3.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9724   -3.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -3.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5746   -4.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374   -4.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -4.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -2.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6576   -1.8797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0193   -2.4242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -3.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093   -0.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6220   -0.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157   -0.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4688   -0.9556    0.0000 C   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  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  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
  5 40  1  0  0  0  0
 19 41  1  1  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 17 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3C=C1OC1=C(OC)C(O)=CC4=C1[C@H](CC1=CC=C(OC5=CC(C[C@H]3N(C)CC2)=CC=C5O)C=C1)N(C)CC4

> <INCHI_IDENTIFIER>
InChI=1S/C36H38N2O6/c1-37-13-11-23-19-32(41-3)33-20-26(23)27(37)16-22-7-10-29(39)31(17-22)43-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)18-30(40)35(42-4)36(34)44-33/h5-10,17-20,27-28,39-40H,11-16H2,1-4H3/t27-,28+/m1/s1

> <INCHI_KEY>
GGGLDIBSBGBODX-IZLXSDGUSA-N

> <FORMULA>
C36H38N2O6

> <MOLECULAR_WEIGHT>
594.708

> <EXACT_MASS>
594.272986952

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
64.78377217442319

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,14S)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{9,12}.1^{3,7}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol

> <JCHEM_LOGP>
5.608287127715818

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
9.686908142915954

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.773120052089178

> <JCHEM_PKA_STRONGEST_BASIC>
8.065310227764677

> <JCHEM_POLAR_SURFACE_AREA>
83.86

> <JCHEM_REFRACTIVITY>
171.14999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14S)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{9,12}.1^{3,7}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.558   3.149   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.042   2.562   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.018   1.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.091   0.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.693  -1.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.810  -1.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.782  -0.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.525   0.913   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.886   1.975   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.578   1.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.361   0.752   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.852   1.830   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.858   3.523   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.461  -0.769   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.028  -2.004   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.752  -1.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.840  -0.471   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.157   1.025   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.925   1.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.560   0.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.072  -1.322   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.776  -2.159   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.287  -3.600   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.370  -4.634   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.842  -3.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.179  -2.428   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.043  -5.678   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.491  -6.212   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.193  -5.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.682  -5.799   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.600  -7.395   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.806  -8.371   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.230  -7.754   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.274  -8.960   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.447  -4.668   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.228  -3.509   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       0.036  -4.525   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0      -0.461  -6.106   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.451  -4.102   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.800  -2.592   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       8.604  -0.171   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      10.494  -0.069   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.869  -1.457   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.475  -1.784   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   44                                                  
CONECT   18   17   10   19                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   30   36                                                       
CONECT   36   35    6   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39    5                                                       
CONECT   41   19   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   17                                                       
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₃₈N₂O₆

Average Mass

594.7080 Da

Monoisotopic Mass

594.27299 Da

IUPAC Name

(1R,14S)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{9,12}.1^{3,7}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3C=C1OC1=C(OC)C(O)=CC4=C1[C@H](CC1=CC=C(OC5=CC(C[C@H]3N(C)CC2)=CC=C5O)C=C1)N(C)CC4

InChI Identifier

InChI=1S/C36H38N2O6/c1-37-13-11-23-19-32(41-3)33-20-26(23)27(37)16-22-7-10-29(39)31(17-22)43-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)18-30(40)35(42-4)36(34)44-33/h5-10,17-20,27-28,39-40H,11-16H2,1-4H3/t27-,28+/m1/s1

InChI Key

GGGLDIBSBGBODX-IZLXSDGUSA-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, 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
Berberis aquifolium	LOTUS Database	35616633
Berberis lycium	LOTUS Database	35616633

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
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
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	5.61	ChemAxon
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	8.07	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	171.15 m³·mol⁻¹	ChemAxon
Polarizability	64.78 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102247461

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

Bezakova L, Misik V, Malekova L, Svajdlenka E, Kostalova D: Lipoxygenase inhibition and antioxidant properties of bisbenzylisoqunoline alkaloids isolated from Mahonia aquifolium. Pharmazie. 1996 Oct;51(10):758-61. [PubMed:8941945 ]
Hajnicka V, Kost'alova D, Svecova D, Sochorova R, Fuchsberger N, Toth J: Effect of Mahonia aquifolium active compounds on interleukin-8 production in the human monocytic cell line THP-1. Planta Med. 2002 Mar;68(3):266-8. doi: 10.1055/s-2002-23126. [PubMed:11914967 ]
LOTUS database [Link]

Showing NP-Card for (1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol (NP0222673)

MOL for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

3D MOL for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

3D SDF for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

3D-SDF for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

PDB for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

3D PDB for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

SMILES for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

INCHI for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

Structure for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)

3D Structure for NP0222673 ((1r,14s)-21,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2⁹,¹².1³,⁷.1¹⁴,¹⁸.0²⁷,³¹.0²²,³³]hexatriaconta-3,5,7(36),9,11,18(33),19,21,24(32),25,27(31),34-dodecaene-6,20-diol)