NP-MRD: Showing NP-Card for Demethyl tetrandrine (NP0138820)

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Record Information

Version

1.0

Created at

2022-06-29 19:18:34 UTC

Updated at

2022-06-29 19:18:34 UTC

NP-MRD ID

NP0138820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethyl tetrandrine

Description

Fangchinoline, also known as limacine or thaligine, 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. Demethyl tetrandrine is found in Abuta grandifolia, Arcangelisia flava, Berberis cretica, Berberis laurina, Cyclea barbata, Gyrocarpus americanus, Spirospermum penduliflorum, Stephania pierrei, Thalictrum pubescens and Thalictrum sachalinense. It was first documented in 2022 (PMID: 35867025). Based on a literature review a significant number of articles have been published on Fangchinoline (PMID: 35865104) (PMID: 35778370) (PMID: 35746702) (PMID: 35700820).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221182D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221182D          

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    8.4623   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -2.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2170   -2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7879   -1.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1995   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194   -0.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9938   -1.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3528   -0.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5130   -0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0209    0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471    0.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1939    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0234    2.4434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6921    3.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5543    2.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618    2.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1149    3.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019    4.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    4.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026    3.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    4.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0791    3.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470    2.7541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143    2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4821    4.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2644    5.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167    3.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1762   -1.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8850    3.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6276    3.4481    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  1  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 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
  8 30  1  0  0  0  0
 29 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
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 27 37  1  1  0  0  0
 37 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
 31 41  1  0  0  0  0
 21 42  1  0  0  0  0
 42 43  1  0  0  0  0
  7 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC3=CC=C(C[C@@H]4N(C)CCC5=CC(OC)=C(OC6=C7[C@@H](CC(C=C1)=C2)N(C)CCC7=CC(OC)=C6O)C=C45)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m0/s1

> <INCHI_KEY>
IIQSJHUEZBTSAT-URLMMPGGSA-N

> <FORMULA>
C37H40N2O6

> <MOLECULAR_WEIGHT>
608.735

> <EXACT_MASS>
608.288637016

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
66.59059850576325

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,14R)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24,26,31,35-dodecaen-21-ol

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
6.050110928197637

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.198443731818413

> <JCHEM_PKA_STRONGEST_BASIC>
9.259350589897657

> <JCHEM_POLAR_SURFACE_AREA>
72.86000000000001

> <JCHEM_REFRACTIVITY>
175.6323

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14R)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24,26,31,35-dodecaen-21-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      19.393  -2.856   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      19.457  -1.317   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      20.820  -0.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.886   0.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.575   1.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.642   3.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.340   4.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.909   3.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.871   2.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.175   1.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.125  -0.487   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.133  -1.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.796  -2.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.017  -4.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.472  -4.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.671  -2.757   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.439  -1.375   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.969  -1.387   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.188  -2.159   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.992  -1.048   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.424  -1.199   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.506   0.052   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.115   1.497   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.695   1.715   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.575   0.416   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.598   3.053   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.244   4.561   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.492   5.629   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.101   5.259   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.422   4.269   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.148   6.411   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.750   7.895   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.236   8.284   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.138   7.166   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.660   7.673   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.481   6.661   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       9.794   5.141   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       8.613   4.153   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      15.833   8.990   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      15.427  10.475   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      16.644   6.048   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       7.796  -2.605   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.699  -3.852   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.452   5.765   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      19.838   6.436   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   44                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   42                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28   37                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29    8                                                       
CONECT   31   29   32   41                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   28   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   27   38                                                  
CONECT   38   37                                                            
CONECT   39   32   40                                                       
CONECT   40   39                                                            
CONECT   41   31                                                            
CONECT   42   21   43                                                       
CONECT   43   42                                                            
CONECT   44    7   45                                                       
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Value	Source
Limacine	MeSH
(1beta)-Isomer OF fangchinoline	MeSH
7-O-Demethyl-tetrandrine	MeSH
Thaligine	MeSH
7-O-Demethyltetrandrine	MeSH
Isofangchinoline	MeSH
Thalrugosine	MeSH

Chemical Formula

C₃₇H₄₀N₂O₆

Average Mass

608.7350 Da

Monoisotopic Mass

608.28864 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

33889-68-8

SMILES

COC1=C2OC3=CC=C(C[C@@H]4N(C)CCC5=CC(OC)=C(OC6=C7[C@@H](CC(C=C1)=C2)N(C)CCC7=CC(OC)=C6O)C=C45)C=C3

InChI Identifier

InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m0/s1

InChI Key

IIQSJHUEZBTSAT-URLMMPGGSA-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
Abuta grandifolia	LOTUS Database	35616633
Arcangelisia flava	LOTUS Database	35616633
Berberis cretica	LOTUS Database	35616633
Berberis laurina	LOTUS Database	35616633
Cyclea barbata	LOTUS Database	35616633
Gyrocarpus americanus	LOTUS Database	35616633
Spirospermum penduliflorum	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Thalictrum polygamum	LOTUS Database	35616633
Thalictrum sachalinense	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
Alkyl aryl ether
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

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025306

Chemspider ID

90605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fangchinoline

METLIN ID

Not Available

PubChem Compound

100257

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jung YY, Um JY, Sethi G, Ahn KS: Fangchinoline abrogates growth and survival of hepatocellular carcinoma by negative regulation of c-met/HGF and its associated downstream signaling pathways. Phytother Res. 2022 Jul 22. doi: 10.1002/ptr.7573. [PubMed:35867025 ]
Cao Y, Fang J, Shi Y, Wang H, Chen X, Liu Y, Zhu Z, Cao Y, Hong Z, Chai Y: Screening potential P-glycoprotein inhibitors by combination of a detergent-free membrane protein extraction with surface plasmon resonance biosensor. Acta Pharm Sin B. 2022 Jul;12(7):3113-3123. doi: 10.1016/j.apsb.2022.03.016. Epub 2022 Mar 29. [PubMed:35865104 ]
Yu X, Liang TH, Wang M, Ren XL, Zhou ZY, Jiang MM, Zhang DQ: An innovative extraction strategy for herbal medicine by adopting p-sulphonatocalix[6]/[8]arenes. Phytochem Anal. 2022 Oct;33(7):1068-1085. doi: 10.1002/pca.3160. Epub 2022 Jul 1. [PubMed:35778370 ]
Dong S, Yu R, Wang X, Chen B, Si F, Zhou J, Xie C, Li Z, Zhang D: Bis-Benzylisoquinoline Alkaloids Inhibit Porcine Epidemic Diarrhea Virus In Vitro and In Vivo. Viruses. 2022 Jun 6;14(6). pii: v14061231. doi: 10.3390/v14061231. [PubMed:35746702 ]
Chen B, Song Y, Zhan Y, Zhou S, Ke J, Ao W, Zhang Y, Liang Q, He M, Li S, Xie F, Huang H, Chan WN, Cheung AHK, Ma BBY, Kang W, To KF, Xiao J: Fangchinoline inhibits non-small cell lung cancer metastasis by reversing epithelial-mesenchymal transition and suppressing the cytosolic ROS-related Akt-mTOR signaling pathway. Cancer Lett. 2022 Sep 1;543:215783. doi: 10.1016/j.canlet.2022.215783. Epub 2022 Jun 11. [PubMed:35700820 ]

Showing NP-Card for Demethyl tetrandrine (NP0138820)

MOL for NP0138820 (Demethyl tetrandrine)

3D MOL for NP0138820 (Demethyl tetrandrine)

3D SDF for NP0138820 (Demethyl tetrandrine)

3D-SDF for NP0138820 (Demethyl tetrandrine)

PDB for NP0138820 (Demethyl tetrandrine)

3D PDB for NP0138820 (Demethyl tetrandrine)

SMILES for NP0138820 (Demethyl tetrandrine)

INCHI for NP0138820 (Demethyl tetrandrine)

Structure for NP0138820 (Demethyl tetrandrine)

3D Structure for NP0138820 (Demethyl tetrandrine)