NP-MRD: Showing NP-Card for (S)-Norreticuline (NP0076915)

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Record Information

Version

2.0

Created at

2022-04-28 22:06:03 UTC

Updated at

2022-04-28 22:06:03 UTC

NP-MRD ID

NP0076915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-Norreticuline

Description

(S)-norreticuline belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (S)-norreticuline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (S)-Norreticuline is found in Erythrina crista-galli , Erythrina verna, Glaucium flavum and Papaver somniferum . (S)-Norreticuline was first documented in 2013 (PMID: 24274926). Based on a literature review a small amount of articles have been published on (S)-norreticuline (PMID: 32881661) (PMID: 26297140) (PMID: 25909585) (PMID: 23738019).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    6.9550    0.9333    1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    0.2839    0.1268 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598    0.4050    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260    1.1844    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597    1.2654    0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761    0.5653   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5231    0.6963   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.3187    0.6370 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0865   -1.6562    0.3059 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -2.4389   -0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -1.6436   -1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453   -0.6515   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7784   -0.3990   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857    0.5250    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7313    0.8234    0.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5551    0.2264   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6450    1.1608    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    2.0920    1.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2976    0.8780    1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583   -0.0399    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7116   -0.2200   -1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0931   -0.3089   -0.9145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154   -1.1016   -1.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8909    0.3849    2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0070    0.8788    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7175    1.9922    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365    1.7322    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    1.9097    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334    0.6526   -1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2412    1.6991    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356   -0.1665    1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6765   -2.1401    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5916   -2.8442    0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -3.3222   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757   -2.3290   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -1.1735   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3280   -0.9206   -1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6075    0.4616   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4186   -0.8809   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3131    0.5523   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2515    2.2913    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121    1.3866    2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -0.7866   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865   -1.6385   -2.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 20  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 20  8  1  0
  8  7  1  0
  7  6  1  0
  6 21  2  0
 21 22  1  0
 22 23  1  0
 22  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 17 14  1  0
  5  6  1  0
 11 12  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 13 37  1  0
 19 42  1  0
 18 41  1  0
  8 31  1  1
  7 29  1  0
  7 30  1  0
 21 43  1  0
 23 44  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
M  END


  Mrv1652304292200062D          

 23 25  0  0  1  0            999 V2000
   -1.4289   -1.6500    0.0000 O   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
    0.0000   -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 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  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
    2.1434    2.0625    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
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)[C@H](CC1=CC(O)=C(OC)C=C1)NCC2

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-22-17-4-3-11(8-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3/t14-/m0/s1

> <INCHI_KEY>
FVEMXQCEJGGXJB-AWEZNQCLSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.369

> <EXACT_MASS>
315.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.27694517823548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.4744308362741734

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.389556434523996

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.790164982818228

> <JCHEM_PKA_STRONGEST_BASIC>
8.618912591374746

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
88.54160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-norreticuline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    6   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   11                                                       
CONECT   20    5   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(-)-Norreticuline	ChEBI
Norreticuline, (R)-isomer	MeSH
Norreticuline	MeSH
Norreticuline, (S)-isomer	MeSH
Norreticuline, hydrochloride, (S)-isomer	MeSH

Chemical Formula

C₁₈H₂₁NO₄

Average Mass

315.3690 Da

Monoisotopic Mass

315.14706 Da

IUPAC Name

(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

(-)-norreticuline

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)[C@H](CC1=CC(O)=C(OC)C=C1)NCC2

InChI Identifier

InChI=1S/C18H21NO4/c1-22-17-4-3-11(8-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3/t14-/m0/s1

InChI Key

FVEMXQCEJGGXJB-AWEZNQCLSA-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
Erythrina crista-galli	Plant	KNApSAcK
Erythrina verna	Plant	KNApSAcK
Glaucium flavum	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

norreticuline (CHEBI:28611 )
Isoquinoline alkaloids (C06520 )

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	2.17	ALOGPS
logP	2.47	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	8.62	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	4	ChemAxon
Refractivity	88.54 m³·mol⁻¹	ChemAxon
Polarizability	34.28 Å³	ChemAxon
Number of Rings	3	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

C00039868

Chemspider ID

389875

KEGG Compound ID

C06520

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441069

PDB ID

Not Available

ChEBI ID

28611

Good Scents ID

Not Available

References

General References

Shah A, Patel V, Parmar B: Discovery of Some Antiviral Natural Products to Fight Against Novel Coronavirus (SARS-CoV-2) Using an In silico Approach. Comb Chem High Throughput Screen. 2021;24(8):1271-1280. doi: 10.2174/1386207323666200902135928. [PubMed:32881661 ]
Chang L, Hagel JM, Facchini PJ: Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant Physiol. 2015 Oct;169(2):1127-40. doi: 10.1104/pp.15.01240. Epub 2015 Aug 21. [PubMed:26297140 ]
Ruiz-Olalla A, Wurdemann MA, Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H: Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids. J Org Chem. 2015 May 15;80(10):5125-32. doi: 10.1021/acs.joc.5b00509. Epub 2015 May 7. [PubMed:25909585 ]
Dion I, Vincent-Rocan JF, Zhang L, Cebrowski PH, Lebrun ME, Pfeiffer JY, Bedard AC, Beauchemin AM: Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products. J Org Chem. 2013 Dec 20;78(24):12735-49. doi: 10.1021/jo4023149. Epub 2013 Dec 4. [PubMed:24274926 ]
Pathak S, Lakhwani D, Gupta P, Mishra BK, Shukla S, Asif MH, Trivedi PK: Comparative transcriptome analysis using high papaverine mutant of Papaver somniferum reveals pathway and uncharacterized steps of papaverine biosynthesis. PLoS One. 2013 May 30;8(5):e65622. doi: 10.1371/journal.pone.0065622. Print 2013. [PubMed:23738019 ]

Showing NP-Card for (S)-Norreticuline (NP0076915)

MOL for NP0076915 ((S)-Norreticuline)

3D MOL for NP0076915 ((S)-Norreticuline)

3D SDF for NP0076915 ((S)-Norreticuline)

3D-SDF for NP0076915 ((S)-Norreticuline)

PDB for NP0076915 ((S)-Norreticuline)

3D PDB for NP0076915 ((S)-Norreticuline)

SMILES for NP0076915 ((S)-Norreticuline)

INCHI for NP0076915 ((S)-Norreticuline)

Structure for NP0076915 ((S)-Norreticuline)

3D Structure for NP0076915 ((S)-Norreticuline)