NP-MRD: Showing NP-Card for Oxyacanthine (NP0051011)

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Record Information

Version

2.0

Created at

2022-04-27 22:27:46 UTC

Updated at

2022-04-27 22:27:46 UTC

NP-MRD ID

NP0051011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxyacanthine

Description

Oxyacanthine, also known as vinetine, 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. Oxyacanthine is found in Berberies floribunda, Berberies integerrima, Berberies julianae, Berberies lambertii, Berberies oblonga, Berberies orthobotrys, Berberies thunbergii, Berberies tschonoskiana, Berberies vulgaris , Berberis aemulans, Berberis amurensis , Berberis aquifolium, Berberis baluchistanica, Berberis candidula, Berberis chitria, Berberis crataegina , Berberis cretica, Berberis densiflora, Berberis fendleri, Berberis heterobotrys, Berberis heteropoda, Berberis integerrima, Berberis lycium, Berberis nummularia, Berberis numularis, Berberis oblonga, Berberis orthobotrys, Berberis poirettii, Berberis pseudanubalata, Berberis sibirica , Berberis thunbergii, Berberis turcomanica, Berberis vulgaris , Berberis wilsoniae, Dehaasia incrassata, Laurelia sempervirens, Mahonia acanthifolia, Mahonia aquifolium, Mahonia borealis, Mahonia fortunei, Mahonia griffithii, Mahonia leschenaultii, Mahonia manipurensis, Mahonia repens , Mahonia sikkimensis, Mahonia simonsii, Stephania cephalantha, Thalictrum atriplex, Thalictrum cultratum, Thalictrum faberi, Thalictrum foliolosum , Thalictrum glandulosissimum, Thalictrum lucidum, Thalictrum microgynum, Thalictrum minus, Thalictrum thunbergii, Thalictrum petaloideum, Thalictrum simplex and Xanthorhiza simplicissima. Oxyacanthine was first documented in 2016 (PMID: 27319140). Based on a literature review a small amount of articles have been published on oxyacanthine (PMID: 34649146) (PMID: 32884211) (PMID: 29888027).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282200272D          

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   -0.5431    0.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320   -0.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687   -0.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037    0.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9164    1.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105    0.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457    0.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1706   -0.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170   -0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853   -0.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644    0.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9067    1.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460    0.8915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9811    0.2180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -0.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358   -0.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4481    0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    0.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7999    0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251   -0.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8066   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -1.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -2.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7818   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -3.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4881   -3.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -2.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315   -2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701   -2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1779   -2.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3861   -2.0643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0128   -2.8024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498   -3.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2563   -2.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411   -0.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.2318    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  1 41  1  0  0  0  0
 39 42  1  0  0  0  0
 27 43  1  0  0  0  0
 13 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(C[C@H]6N(C)CCC7=CC(OC)=C(OC3=C1OC)C=C67)=CC=C5O)C=C4)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)17-23-8-11-30(40)31(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m1/s1

> <INCHI_KEY>
HGNHIFJNOKGSKI-WDYNHAJCSA-N

> <FORMULA>
C37H40N2O6

> <MOLECULAR_WEIGHT>
608.735

> <EXACT_MASS>
608.288637016

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
66.20834369479294

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,14S)-20,21,25-trimethoxy-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),19,21,24,26,31,34-dodecaen-6-ol

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
5.787672016796062

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.82443139

> <JCHEM_PKA_STRONGEST_BASIC>
8.070817512456989

> <JCHEM_POLAR_SURFACE_AREA>
72.86

> <JCHEM_REFRACTIVITY>
175.63229999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14S)-20,21,25-trimethoxy-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),19,21,24,26,31,34-dodecaen-6-ol

> <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      -1.840  -2.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274  -2.500   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.102  -0.866   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.014   0.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.486  -0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.928  -1.633   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.551   0.948   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.047   0.583   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.619   1.696   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.711   2.782   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.766   0.638   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.139   1.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.185  -0.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.392  -0.919   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.639  -0.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.974   1.415   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.559   2.226   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.619   1.664   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.431   0.407   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.948  -1.028   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.480  -1.317   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.960   0.598   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.303   1.562   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.272   0.165   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.827   0.076   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.620  -1.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.839  -2.617   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.261  -2.775   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.620  -1.321   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.317  -4.147   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.059  -5.188   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.245  -6.536   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.644  -6.626   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.728  -5.336   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.539  -4.017   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.104  -3.977   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.199  -4.696   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.721  -3.853   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      -0.024  -5.231   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      -1.560  -5.409   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.489  -4.177   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.840  -6.506   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.678  -3.908   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.823  -0.760   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       0.765  -2.299   0.000  0.00  0.00           C+0
CONECT    1    2    6   41                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   44                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   15                                                       
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   43                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34   38                                                       
CONECT   38   37    2   39                                                  
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40    1                                                       
CONECT   42   39                                                            
CONECT   43   27                                                            
CONECT   44   13   45                                                       
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Value	Source
Oxycanthine	ChEBI
Vinetine	ChEBI

Chemical Formula

C₃₇H₄₀N₂O₆

Average Mass

608.7350 Da

Monoisotopic Mass

608.28864 Da

IUPAC Name

(1R,14S)-20,21,25-trimethoxy-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),19,21,24,26,31,34-dodecaen-6-ol

Traditional Name

(1R,14S)-20,21,25-trimethoxy-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),19,21,24,26,31,34-dodecaen-6-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(C[C@H]6N(C)CCC7=CC(OC)=C(OC3=C1OC)C=C67)=CC=C5O)C=C4)N(C)CC2

InChI Identifier

InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)17-23-8-11-30(40)31(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m1/s1

InChI Key

HGNHIFJNOKGSKI-WDYNHAJCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Berberies floribunda	-	KNApSAcK
Berberies integerrima	-	KNApSAcK
Berberies julianae	-	KNApSAcK
Berberies lambertii	-	KNApSAcK
Berberies oblonga	-	KNApSAcK
Berberies orthobotrys	-	KNApSAcK
Berberies thunbergii	-	KNApSAcK
Berberies tschonoskiana	-	KNApSAcK
Berberies vulgaris	-	KNApSAcK
Berberis aemulans	Plant	KNApSAcK
Berberis amurensis	Plant	KNApSAcK
Berberis aquifolium	LOTUS Database	35616633
Berberis baluchistanica	Plant	KNApSAcK
Berberis candidula	Plant	KNApSAcK
Berberis chitria	LOTUS Database	35616633
Berberis crataegina	Plant	KNApSAcK
Berberis cretica	LOTUS Database	35616633
Berberis densiflora	Plant	KNApSAcK
Berberis fendleri	LOTUS Database	35616633
Berberis heterobotrys	Plant	KNApSAcK
Berberis heteropoda	LOTUS Database	35616633
Berberis integerrima	Plant	KNApSAcK
Berberis lycium	LOTUS Database	35616633
Berberis nummularia	LOTUS Database	35616633
Berberis numularis	Plant	KNApSAcK
Berberis oblonga	Plant	KNApSAcK
Berberis orthobotrys	LOTUS Database	35616633
Berberis poirettii	Plant	KNApSAcK
Berberis pseudanubalata	Plant	KNApSAcK
Berberis sibirica	Plant	KNApSAcK
Berberis thunbergii	LOTUS Database	35616633
Berberis turcomanica	Plant	KNApSAcK
Berberis vulgaris	Plant	KNApSAcK
Berberis wilsoniae	LOTUS Database	35616633
Dehaasia incrassata	Plant	KNApSAcK
Laurelia sempervirens	LOTUS Database	35616633
Mahonia acanthifolia	Plant	KNApSAcK
Mahonia aquifolium	Plant	KNApSAcK
Mahonia borealis	Plant	KNApSAcK
Mahonia fortunei	Plant	KNApSAcK
Mahonia griffithii	Plant	KNApSAcK
Mahonia leschenaultii	Plant	KNApSAcK
Mahonia manipurensis	Plant	KNApSAcK
Mahonia repens	Plant	KNApSAcK
Mahonia sikkimensis	Plant	KNApSAcK
Mahonia simonsii	Plant	KNApSAcK
Stephania cephalantha	LOTUS Database	35616633
Thalictrum atriplex	Plant	KNApSAcK
Thalictrum cultratum	LOTUS Database	35616633
Thalictrum faberi	Plant	KNApSAcK
Thalictrum foliolosum	Plant	KNApSAcK
Thalictrum glandulosissimum	Plant	KNApSAcK
Thalictrum lucidum	Plant	KNApSAcK
Thalictrum microgynum	Plant	KNApSAcK
Thalictrum minus	Plant	KNApSAcK
Thalictrum minus var. hypoleucum	Plant	KNApSAcK
Thalictrum petaloideum	Plant	KNApSAcK
Thalictrum simplex	Plant	KNApSAcK
Xanthorhiza simplicissima	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Diaryl ether
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:7853 )
phenols (CHEBI:7853 )
benzylisoquinoline alkaloid (CHEBI:7853 )
macrocycle (CHEBI:7853 )
isoquinolines (CHEBI:7853 )
Isoquinoline alkaloids (C09598 )

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	5.52	ALOGPS
logP	5.79	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.82	ChemAxon
pKa (Strongest Basic)	8.07	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	175.63 m³·mol⁻¹	ChemAxon
Polarizability	66.21 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

C00001897

Chemspider ID

390787

KEGG Compound ID

C09598

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442333

PDB ID

Not Available

ChEBI ID

7853

Good Scents ID

Not Available

References

General References

Joshi T, Bhat S, Pundir H, Chandra S: Identification of Berbamine, Oxyacanthine and Rutin from Berberis asiatica as anti-SARS-CoV-2 compounds: An in silico study. J Mol Graph Model. 2021 Dec;109:108028. doi: 10.1016/j.jmgm.2021.108028. Epub 2021 Oct 11. [PubMed:34649146 ]
Kirubhanand C, Selvaraj J, Rekha UV, Vishnupriya V, Sivabalan V, Manikannan M, Nalini D, Vijayalakshmi P, Rajalakshmi M, Ponnulakshmi R: Molecular docking analysis of Bcl-2 with phyto-compounds. Bioinformation. 2020 Jun 30;16(6):468-473. doi: 10.6026/97320630016468. eCollection 2020. [PubMed:32884211 ]
Alamzeb M, Omer M, Ur-Rashid M, Raza M, Ali S, Khan B, Ullah A: NMR, Novel Pharmacological and In Silico Docking Studies of Oxyacanthine and Tetrandrine: Bisbenzylisoquinoline Alkaloids Isolated from Berberis glaucocarpa Roots. J Anal Methods Chem. 2018 May 16;2018:7692913. doi: 10.1155/2018/7692913. eCollection 2018. [PubMed:29888027 ]
El Hosry L, Boyer L, Garayev EE, Mabrouki F, Bun SS, Debrauwer L, Auezova L, Cheble E, Elias R: Chemical Composition, Antioxidant and Cytotoxic Activities of Roots and Fruits of Berberis libanotica. Nat Prod Commun. 2016 May;11(5):645-8. [PubMed:27319140 ]

Showing NP-Card for Oxyacanthine (NP0051011)

MOL for NP0051011 (Oxyacanthine)

3D MOL for NP0051011 (Oxyacanthine)

3D SDF for NP0051011 (Oxyacanthine)

3D-SDF for NP0051011 (Oxyacanthine)

PDB for NP0051011 (Oxyacanthine)

3D PDB for NP0051011 (Oxyacanthine)

SMILES for NP0051011 (Oxyacanthine)

INCHI for NP0051011 (Oxyacanthine)

Structure for NP0051011 (Oxyacanthine)

3D Structure for NP0051011 (Oxyacanthine)