NP-MRD: Showing NP-Card for (9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium (NP0322652)

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Record Information

Version

2.0

Created at

2022-09-12 01:32:37 UTC

Updated at

2022-09-12 01:32:37 UTC

NP-MRD ID

NP0322652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium

Description

75667-86-6 Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. (9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium is found in Pachygone ovata. Based on a literature review very few articles have been published on 75667-86-6.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    3.5583    0.3347    2.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.1318    1.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9088    0.7563    1.2409 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3301    1.4015   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377    0.2501   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133   -0.5810   -1.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9677   -1.8107   -1.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -2.6034   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756   -1.6310   -0.2815 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.5504   -1.5514   -1.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518   -1.8550    0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740   -0.6632    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0560    0.4284    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873    1.3121   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475    2.3321   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7564    2.4850   -1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5902    3.5241   -2.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7380    1.6205   -1.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491    0.6163   -0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752   -0.3831   -0.2140 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6116    0.0066    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667    0.3530    3.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148   -0.2604    3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074    1.3995    2.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595    1.5792    1.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697    2.2614   -0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282    1.6217    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636    0.0685   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268   -1.5959   -2.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -2.3234   -2.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1911   -2.8083   -0.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202   -3.4711   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4115   -0.6589   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -1.6091   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -2.4954   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -2.1472    1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -2.7314    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057   -0.2768    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608   -0.9870    0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0504    1.2383    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7572    3.0327   -1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335    4.3867   -2.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    1.7294   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.8566    1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.6941    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  1
 21  3  1  0
 20  6  1  0
 20  9  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
M  CHG  1   9   1
M  END


  Mrv1652309122203322D          

 21 24  0  0  1  0            999 V2000
    3.4259   -1.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -0.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8059   -1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334    0.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413    1.0588    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.3440    1.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    1.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    1.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158    1.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415    0.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -1.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416    0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669    0.3521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0770    0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  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
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  6  1  6  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
M  CHG  1   9   1
M  END
> <DATABASE_ID>
NP0322652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CC=C2CC[N+]3(C)CCC4=CC=C(O)C=C4[C@]23C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO2/c1-19-9-7-13-3-5-15(20)11-17(13)18(19)12-16(21-2)6-4-14(18)8-10-19/h3-5,11,16H,6-10,12H2,1-2H3/p+1/t16-,18-,19?/m0/s1

> <INCHI_KEY>
ZZOIDXABHPNSHY-SPIBDARASA-O

> <FORMULA>
C18H24NO2

> <MOLECULAR_WEIGHT>
286.394

> <EXACT_MASS>
286.180155437

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.35499203300549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,16S)-4-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-10-ium

> <JCHEM_LOGP>
-2.040903440805079

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.356423395564066

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126994236222327

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
96.5987

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,16S)-4-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,4,6,13-tetraen-10-ium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.395  -2.838   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.892  -1.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.380  -1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.371  -2.254   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.859  -1.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.356  -0.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.062   0.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.070   1.628   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.570   1.976   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0       0.642   3.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.315   3.324   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.855   3.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.650   2.034   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.190   2.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.984   0.743   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.239  -0.605   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.034  -1.924   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.699  -0.633   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.624   1.019   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.365   0.657   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.877   0.365   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19    6    9   21                                             
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₄NO₂

Average Mass

286.3940 Da

Monoisotopic Mass

286.18016 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC=C2CC[N+]3(C)CCC4=CC=C(O)C=C4[C@]23C1

InChI Identifier

InChI=1S/C18H23NO2/c1-19-9-7-13-3-5-15(20)11-17(13)18(19)12-16(21-2)6-4-14(18)8-10-19/h3-5,11,16H,6-10,12H2,1-2H3/p+1/t16-,18-,19?/m0/s1

InChI Key

ZZOIDXABHPNSHY-SPIBDARASA-O

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
Pachygone ovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Tetraalkylammonium salt
Quaternary ammonium salt
Pyrrolidine
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Amine
Organic cation
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

C00026000

Chemspider ID

138034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156796

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium (NP0322652)

MOL for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

3D MOL for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

3D SDF for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

3D-SDF for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

PDB for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

3D PDB for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

SMILES for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

INCHI for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

Structure for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)

3D Structure for NP0322652 ((9bs,11s)-8-hydroxy-11-methoxy-3-methyl-1h,2h,4h,5h,10h,11h,12h-indolo[7a,1-a]isoquinolin-3-ium)