NP-MRD: Showing NP-Card for 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol (NP0301794)

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Record Information

Version

2.0

Created at

2022-09-10 14:58:07 UTC

Updated at

2022-09-10 14:58:07 UTC

NP-MRD ID

NP0301794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol

Description

1',2',3',4'-Tetradehydrotubulosine belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol is found in Pogonopus speciosus. 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol was first documented in 1999 (PMID: 10514334). Based on a literature review very few articles have been published on 1',2',3',4'-Tetradehydrotubulosine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216582D          

 35 40  0  0  1  0            999 V2000
   12.1332    1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5811    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8361   -0.3207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6431   -0.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8980   -1.2769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7050   -1.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9599   -2.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4079   -2.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6628   -3.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1108   -4.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3657   -5.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8137   -5.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3038   -4.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7518   -4.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9448   -4.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0489   -3.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6009   -2.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3460   -1.8899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5390   -1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2840   -0.9338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.2221    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5192    1.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7123    1.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1602    0.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4152    0.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7477   -0.2910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    0.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7213    0.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9762    1.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4242    2.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7832    1.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3352    0.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  8 17  1  0  0  0  0
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 18  5  1  6  0  0  0
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  3 20  1  0  0  0  0
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 34 35  1  0  0  0  0
 29 35  2  0  0  0  0
 26 35  1  0  0  0  0
M  END

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309102216582D          

 35 40  0  0  1  0            999 V2000
   12.1332    1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5811    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 29 35  2  0  0  0  0
 26 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1CC1=NC=CC2=C1NC1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H33N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-7,9,13-15,17,19,26,31,33H,4,8,10-12,16H2,1-3H3/t17-,19-,26-/m0/s1

> <INCHI_KEY>
FYIJNEXYFHEJLZ-IAKTWSEQSA-N

> <FORMULA>
C29H33N3O3

> <MOLECULAR_WEIGHT>
471.601

> <EXACT_MASS>
471.252191935

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.905273116279524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9H-pyrido[3,4-b]indol-6-ol

> <JCHEM_LOGP>
4.392098554186196

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.329760878481402

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.512673802474803

> <JCHEM_PKA_STRONGEST_BASIC>
8.617814621965067

> <JCHEM_POLAR_SURFACE_AREA>
70.61

> <JCHEM_REFRACTIVITY>
137.7805

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-{[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9H-pyrido[3,4-b]indol-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      22.649   2.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.618   0.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.094  -0.599   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.600  -0.919   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      24.076  -2.383   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      25.583  -2.704   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.058  -4.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.028  -5.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.504  -6.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.473  -7.922   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      24.949  -9.386   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      23.919 -10.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.967  -7.602   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.937  -8.746   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      20.430  -8.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.491  -6.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.522  -4.993   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.046  -3.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.539  -3.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.064  -1.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.557  -1.423   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.081   0.042   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      20.112   1.186   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      19.636   2.651   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.130   2.971   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.099   1.827   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.575   0.362   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      16.329  -0.543   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      15.083   0.362   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.577   0.042   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.546   1.186   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.022   2.651   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.992   3.795   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.529   2.971   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.559   1.827   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29   26                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
1',2',3',4'-Tetradehydro-tubulosine	MeSH

Chemical Formula

C₂₉H₃₃N₃O₃

Average Mass

471.6010 Da

Monoisotopic Mass

471.25219 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1CC1=NC=CC2=C1NC1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C29H33N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-7,9,13-15,17,19,26,31,33H,4,8,10-12,16H2,1-3H3/t17-,19-,26-/m0/s1

InChI Key

FYIJNEXYFHEJLZ-IAKTWSEQSA-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
Pogonopus speciosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Hydroxyindole
Quinolizidine
Tetrahydroisoquinoline
Indole
Indole or derivatives
Anisole
Phenol ether
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Piperidine
Pyridine
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
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

C00049409

Chemspider ID

10276277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21668793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ito A, Lee YH, Chai HB, Gupta MP, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD: 1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus. J Nat Prod. 1999 Sep;62(9):1346-8. doi: 10.1021/np990255u. [PubMed:10514334 ]
LOTUS database [Link]

Showing NP-Card for 1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol (NP0301794)

MOL for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

3D MOL for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

3D SDF for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

3D-SDF for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

PDB for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

3D PDB for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

SMILES for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

INCHI for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

Structure for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)

3D Structure for NP0301794 (1-{[(2r,3r,11bs)-3-ethyl-9,10-dimethoxy-1h,2h,3h,4h,6h,7h,11bh-pyrido[2,1-a]isoquinolin-2-yl]methyl}-9h-pyrido[3,4-b]indol-6-ol)