NP-MRD: Showing NP-Card for Norisoboldine (NP0074469)

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Record Information

Version

2.0

Created at

2022-04-28 19:43:25 UTC

Updated at

2022-04-28 19:43:25 UTC

NP-MRD ID

NP0074469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Norisoboldine

Description

NORISOBOLDINE belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Norisoboldine is found in Beilschmiedia elliptica, Cassytha pubescens, Cocculus laurifolius, Croton lechleri, Croton lechleri Mull.Arg. , Fissistigma oldhamii, Guatteria dumetorum, Houttuynia cordata , Illigera pentaphylla, Litsea acuminata, Pachygone ovata, Monanthotaxis cauliflora, Stephania cephalantha and Zizyphus jujuba . Norisoboldine was first documented in 2018 (PMID: 30036998). Based on a literature review a significant number of articles have been published on NORISOBOLDINE (PMID: 35233835) (PMID: 34743982) (PMID: 34719823) (PMID: 34602563) (PMID: 34415684) (PMID: 33556569).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    4.7606    1.7558   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536    0.3465   -0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568   -0.3398   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    0.3252   -0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1986   -0.4216   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2161   -1.8013   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4428   -2.4427   -0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6110   -1.7166   -0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8228   -2.3968   -0.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -2.6199   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -1.9821    0.4192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3615   -2.6989    0.2940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -2.0052    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -0.7687    0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902    0.0613    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5726    1.4182    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    2.1889   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    3.5575   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7965    4.2148   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    1.6051   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    2.4461   -0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998    0.2371   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -0.5478    0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    2.2018   -1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8004    2.0798   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5479    2.1468    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983    1.3730   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313   -3.5309   -0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8353   -3.3867   -0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -2.7419   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.6601   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8037   -2.0887    1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654   -3.6918    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7129   -1.6595    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378   -2.6407    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990   -1.1278   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5176   -0.2260    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5622    1.8845    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    5.2700   -0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1467    4.2261    0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5651    3.7213   -0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7690    3.4356   -0.3686 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
 22  5  1  0
 23 11  1  0
 23 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  1
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
  7 28  1  0
  9 29  1  0
M  END


  Mrv1652304282221432D          

 23 26  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   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  1  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
  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 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H]3NCCC4=CC(OC)=C(O)C2=C34)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO4/c1-22-14-8-11-10(6-13(14)20)5-12-16-9(3-4-19-12)7-15(23-2)18(21)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/m0/s1

> <INCHI_KEY>
HORZNQYQXBFWNZ-LBPRGKRZSA-N

> <FORMULA>
C18H19NO4

> <MOLECULAR_WEIGHT>
313.353

> <EXACT_MASS>
313.131408096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.734954348465756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-4,15-dimethoxy-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,16-diol

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
2.0205215933423024

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.250605610733533

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.591174396974257

> <JCHEM_PKA_STRONGEST_BASIC>
8.761405304230964

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
87.61980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-4,15-dimethoxy-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,16-diol

> <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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    4                                                       
CONECT   14    8   15                                                       
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19    1                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₄

Average Mass

313.3530 Da

Monoisotopic Mass

313.13141 Da

IUPAC Name

(9S)-4,15-dimethoxy-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,16-diol

Traditional Name

(9S)-4,15-dimethoxy-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,16-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C[C@@H]3NCCC4=CC(OC)=C(O)C2=C34)C=C1O

InChI Identifier

InChI=1S/C18H19NO4/c1-22-14-8-11-10(6-13(14)20)5-12-16-9(3-4-19-12)7-15(23-2)18(21)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/m0/s1

InChI Key

HORZNQYQXBFWNZ-LBPRGKRZSA-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
Beilschmiedia elliptica	LOTUS Database	35616633
Cassytha pubescens R.Br.	LOTUS Database	35616633
Cocculus laurifolius	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Croton lechleri Mull.Arg.	Plant	KNApSAcK
Fissistigma oldhamii	LOTUS Database	35616633
Guatteria dumetorum	LOTUS Database	35616633
Houttuynia cordata	Plant	KNApSAcK
Illigera pentaphylla	LOTUS Database	35616633
Litsea acuminata	Plant	KNApSAcK
Pachygone ovata	LOTUS Database	35616633
Popowia cauliflora	LOTUS Database	35616633
Stephania cephalantha	LOTUS Database	35616633
Ziziphus jujuba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
1-naphthol
Naphthalene
Tetrahydroisoquinoline
Quinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Azacycle
Secondary aliphatic amine
Ether
Organoheterocyclic compound
Secondary amine
Amine
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen 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
logP	1.71	ALOGPS
logP	2.02	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.62 m³·mol⁻¹	ChemAxon
Polarizability	33.73 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025962

Chemspider ID

23282643

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14539911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He Y, Cheng P, Wang W, Yan S, Tang Q, Liu D, Xie H: Rapid Investigation and Screening of Bioactive Components in Simo Decoction via LC-Q-TOF-MS and UF-HPLC-MD Methods. Molecules. 2018 Jul 20;23(7). pii: molecules23071792. doi: 10.3390/molecules23071792. [PubMed:30036998 ]
Zhang Q, Fang Y, Lv C, Zhu Y, Xia Y, Wei Z, Dai Y: Norisoboldine induces the development of Treg cells by promoting fatty acid oxidation-mediated H3K27 acetylation of Foxp3. FASEB J. 2022 Apr;36(4):e22230. doi: 10.1096/fj.202101643R. [PubMed:35233835 ]
Fang Y, Duan C, Zhang J, Dai Y, Xia Y: NMR-based untargeted metabolomics approach to investigate the systemic lipid metabolism regulation of norisoboldine in collagen-induced arthritis rats. Eur J Pharmacol. 2021 Dec 5;912:174608. doi: 10.1016/j.ejphar.2021.174608. Epub 2021 Oct 28. [PubMed:34743982 ]
Xing D, Li Q, Lin G, Lin H, Kang W, Zhang M, Ding R, Li N: The protective effects of propofol against renal ischemia-reperfusion injury are potentiated by norisoboldine treatment via inhibition of oxidative stress pathways. J Biochem Mol Toxicol. 2022 Jan;36(1):e22937. doi: 10.1002/jbt.22937. Epub 2021 Oct 31. [PubMed:34719823 ]
Chen Q, Shao X, He Y, Lu E, Zhu L, Tang W: Norisoboldine Attenuates Sepsis-Induced Acute Lung Injury by Modulating Macrophage Polarization via PKM2/HIF-1alpha/PGC-1alpha Pathway. Biol Pharm Bull. 2021;44(10):1536-1547. doi: 10.1248/bpb.b21-00457. [PubMed:34602563 ]
Wu X, Long H, Li F, Wu W, Zhou J, Liu C, Hou J, Wu W, Guo D: Comprehensive feature-based molecular networking and metabolomics approaches to reveal the differences components in Cinnamomum cassia and Cinnamomum verum. J Sep Sci. 2021 Oct;44(20):3810-3821. doi: 10.1002/jssc.202100399. Epub 2021 Sep 1. [PubMed:34415684 ]
Chang L, Zhang Q, Tang Y, Fang Y, Dou R, Chu Y, Xia Y, Wei Z, Chen L, Dai Y: Synthesis of norisoboldine derivatives and bioactivity assay for inducing the generation of regulatory T cells. Bioorg Med Chem Lett. 2021 Apr 1;37:127844. doi: 10.1016/j.bmcl.2021.127844. Epub 2021 Feb 5. [PubMed:33556569 ]
Zhang J, Wen X, Dai Y, Xia Y: Mechanistic studies on the absorption enhancement of a self-nanoemulsifying drug delivery system loaded with norisoboldine-phospholipid complex. Int J Nanomedicine. 2019 Sep 2;14:7095-7106. doi: 10.2147/IJN.S211905. eCollection 2019. [PubMed:31564867 ]
Huang M, Su J, Lou Z, Xie F, Pan W, Yang Z, Gu L, Xie F, Xu Z, Zhang L, Liu F, Lai H, Zhang L, Lin N: Application of a DSS colitis model in toxicologically assessing norisoboldine. Toxicol Mech Methods. 2020 Feb;30(2):107-114. doi: 10.1080/15376516.2019.1669242. Epub 2019 Oct 2. [PubMed:31532267 ]

Showing NP-Card for Norisoboldine (NP0074469)

MOL for NP0074469 (Norisoboldine)

3D MOL for NP0074469 (Norisoboldine)

3D SDF for NP0074469 (Norisoboldine)

3D-SDF for NP0074469 (Norisoboldine)

PDB for NP0074469 (Norisoboldine)

3D PDB for NP0074469 (Norisoboldine)

SMILES for NP0074469 (Norisoboldine)

INCHI for NP0074469 (Norisoboldine)

Structure for NP0074469 (Norisoboldine)

3D Structure for NP0074469 (Norisoboldine)