NP-MRD: Showing NP-Card for 8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one (NP0162997)

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Record Information

Version

2.0

Created at

2022-09-02 21:31:54 UTC

Updated at

2022-09-02 21:31:54 UTC

NP-MRD ID

NP0162997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one

Description

4,16-Dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]Heptadeca-2(7),3,5,13,16-pentaen-15-one 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. 8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one is found in Cocculus laurifolius. 4,16-Dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]Heptadeca-2(7),3,5,13,16-pentaen-15-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    1.9394    3.1984    3.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162    1.9765    3.1044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5201    1.2051    1.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6822    0.2293    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.6165    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9722   -0.3548   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918    0.6009   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658    1.4759    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820    2.3768    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -1.4212   -1.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -2.5230   -0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -2.0424    0.7169 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2191   -2.6793    1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449   -2.0410    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5894   -1.0605    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600   -0.8590   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671    0.0544   -1.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581    0.7929   -2.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339    1.7174   -3.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7146    2.0395   -3.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5013    0.5634   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -0.3463   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7270    3.9771    2.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    3.5993    4.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    3.1354    3.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1468    0.1215    2.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341    0.7335   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318   -1.7972   -1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1622   -1.0882   -2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -2.8343   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7247   -3.4440   -0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179   -2.8065    2.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -3.7461    0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -1.5492    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3740   -2.7577    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6146   -1.4485   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6788    0.2196   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    2.4483   -3.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336    2.7145   -4.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1574    1.1047   -4.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1317   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  5  4  1  1
  5 22  1  0
 22 21  2  0
 21 18  1  0
 22 15  1  0
  5 12  1  0
  5  6  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 17 37  1  0
 16 36  1  0
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 11 30  1  0
 11 31  1  0
 10 28  1  0
 10 29  1  0
  7 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 21 41  1  0
M  END


  Mrv1533004201500212D          

 22 25  0  0  0  0            999 V2000
    3.4502    2.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708    1.5328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    0.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -0.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143    1.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8263    2.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056    2.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3515    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6107    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5269    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922    0.4383    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  2  0  0  0  0
  4  5  1  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
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CCN3CCC4=CC(=O)C(OC)=CC34C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-21-14-4-3-12-5-7-19-8-6-13-9-16(20)17(22-2)11-18(13,19)15(12)10-14/h3-4,9-11H,5-8H2,1-2H3

> <INCHI_KEY>
PTSRTUGDUDWNCX-UHFFFAOYSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.354

> <EXACT_MASS>
297.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.48520751640916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,16-dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2,4,6,13,16-pentaen-15-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.0121413396666674

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.22787402259465

> <JCHEM_PKA_STRONGEST_BASIC>
7.181928339173654

> <JCHEM_POLAR_SURFACE_AREA>
38.769999999999996

> <JCHEM_REFRACTIVITY>
87.06630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,16-dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2,4,6,13,16-pentaen-15-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.440   4.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.919   2.861   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.403   2.588   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.769   1.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.366   0.866   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.555  -0.443   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.059  -0.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.054   1.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.372   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.893   3.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.409   3.764   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.930   5.213   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.283  -1.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.822  -1.848   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.634  -0.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.173  -0.587   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.984   0.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.256   2.079   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.067   3.388   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.607   3.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.717   2.127   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.906   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   22                                             
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21    5   15                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₃

Average Mass

297.3540 Da

Monoisotopic Mass

297.13649 Da

IUPAC Name

4,16-dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2,4,6,13,16-pentaen-15-one

Traditional Name

4,16-dimethoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2,4,6,13,16-pentaen-15-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CCN3CCC4=CC(=O)C(OC)=CC34C2=C1

InChI Identifier

InChI=1S/C18H19NO3/c1-21-14-4-3-12-5-7-19-8-6-13-9-16(20)17(22-2)11-18(13,19)15(12)10-14/h3-4,9-11H,5-8H2,1-2H3

InChI Key

PTSRTUGDUDWNCX-UHFFFAOYSA-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
Cocculus laurifolius	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
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
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	2.22	ALOGPS
logP	2.01	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
pKa (Strongest Basic)	7.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.07 m³·mol⁻¹	ChemAxon
Polarizability	31.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

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BiGG ID

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METLIN ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one (NP0162997)

MOL for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

3D MOL for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

3D SDF for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

3D-SDF for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

PDB for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

3D PDB for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

SMILES for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

INCHI for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

Structure for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)

3D Structure for NP0162997 (8,11-dimethoxy-1h,2h,4h,5h-indolo[7a,1-a]isoquinolin-12-one)