NP-MRD: Showing NP-Card for 4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium (NP0205179)

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Record Information

Version

2.0

Created at

2022-09-05 01:02:02 UTC

Updated at

2022-09-05 01:02:02 UTC

NP-MRD ID

NP0205179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium

Description

6-{4,8-Dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-9-methoxy-7λ⁵,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),8,11(16),12,14-hexaen-7-ylium 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. 4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium is found in Picrasma quassioides. Based on a literature review very few articles have been published on 6-{4,8-dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-9-methoxy-7λ⁵,17-diazatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),8,11(16),12,14-hexaen-7-ylium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203022D          

 36 42  0  0  0  0            999 V2000
    6.4546   -4.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6476   -3.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3927   -3.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857   -2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308   -2.2104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828   -1.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6279   -0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8209   -0.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5660    0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 25  1  0  0  0  0
  6 26  2  0  0  0  0
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 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 26 36  1  0  0  0  0
M  CHG  1  25   1
M  END

     RDKit          3D

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    0.0477   -2.3399    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4161    1.3120    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25  7  1  0
 19 20  1  0
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  3 36  1  0
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 31 60  1  0
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 34 63  1  0
  5 41  1  0
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  1 37  1  0
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  1 39  1  0
  7 42  1  1
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 24 57  1  0
 23 54  1  0
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 23 56  1  0
 13 49  1  0
 18 53  1  0
 17 52  1  0
 16 51  1  0
 15 50  1  0
M  CHG  1  25   1
M  END


  Mrv1652309052203022D          

 36 42  0  0  0  0            999 V2000
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    5.6476   -3.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 26 36  1  0  0  0  0
M  CHG  1  25   1
M  END
> <DATABASE_ID>
NP0205179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C3C(N=C12)=C(NC=C3OC)C1CCCC2=[N+]1C=C(OC)C1=C2NC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C29H26N4O3/c1-34-21-13-6-9-17-25-22(35-2)14-30-28(29(25)32-26(17)21)20-12-7-11-19-27-24(23(36-3)15-33(19)20)16-8-4-5-10-18(16)31-27/h4-6,8-10,13-15,20H,7,11-12H2,1-3H3,(H,30,32)/p+1

> <INCHI_KEY>
NQZOCXBXUNDIIB-UHFFFAOYSA-O

> <FORMULA>
C29H27N4O3

> <MOLECULAR_WEIGHT>
479.559

> <EXACT_MASS>
479.207767166

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
53.59289005934918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{4,8-dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-7-methoxy-1H,2H,3H,4H,12H-5lambda5-indolo[2,3-a]quinolizin-5-ylium

> <JCHEM_LOGP>
0.11103086286158821

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.89208559416675

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.215290124326998

> <JCHEM_PKA_STRONGEST_BASIC>
1.8597206629141558

> <JCHEM_POLAR_SURFACE_AREA>
76.04

> <JCHEM_REFRACTIVITY>
138.1162

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{4,8-dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-7-methoxy-1H,2H,3H,4H,12H-5lambda5-indolo[2,3-a]quinolizin-5-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.049  -7.696   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.542  -7.375   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.066  -5.911   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.560  -5.591   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.084  -4.126   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.115  -2.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.639  -1.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.132  -1.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.656   0.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.687   1.412   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.193   1.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.224   2.237   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.063   3.768   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      11.470   4.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.946   5.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.452   6.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.482   5.035   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.006   3.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.500   3.250   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.730   1.916   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.206   0.452   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.712   0.132   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.188  -1.333   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.176  -0.693   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       9.669  -0.372   0.000  0.00  0.00           N+1
HETATM   26  C   UNK     0      10.621  -3.302   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      11.867  -2.397   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      13.113  -3.302   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.619  -2.982   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.095  -1.517   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.601  -1.197   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.650  -4.126   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.174  -5.591   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.667  -5.911   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.637  -4.766   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.097  -4.766   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   12   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   11    7                                                  
CONECT   26    6   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35    3   26                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₇N₄O₃

Average Mass

479.5590 Da

Monoisotopic Mass

479.20777 Da

IUPAC Name

4-{4,8-dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-7-methoxy-1H,2H,3H,4H,12H-5lambda5-indolo[2,3-a]quinolizin-5-ylium

Traditional Name

4-{4,8-dimethoxy-2H-pyrido[3,4-b]indol-1-yl}-7-methoxy-1H,2H,3H,4H,12H-5lambda5-indolo[2,3-a]quinolizin-5-ylium

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C3C(N=C12)=C(NC=C3OC)C1CCCC2=[N+]1C=C(OC)C1=C2NC2=C1C=CC=C2

InChI Identifier

InChI=1S/C29H26N4O3/c1-34-21-13-6-9-17-25-22(35-2)14-30-28(29(25)32-26(17)21)20-12-7-11-19-27-24(23(36-3)15-33(19)20)16-8-4-5-10-18(16)31-27/h4-6,8-10,13-15,20H,7,11-12H2,1-3H3,(H,30,32)/p+1

InChI Key

NQZOCXBXUNDIIB-UHFFFAOYSA-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
Picrasma quassioides	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
Bipyridine
Quinolizine
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Benzenoid
Pyridine
Pyridinium
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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
logP	0.11	ChemAxon
pKa (Strongest Acidic)	10.22	ChemAxon
pKa (Strongest Basic)	1.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.12 m³·mol⁻¹	ChemAxon
Polarizability	53.59 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

10273258

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium (NP0205179)

MOL for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

3D MOL for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

3D SDF for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

3D-SDF for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

PDB for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

3D PDB for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

SMILES for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

INCHI for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

Structure for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)

3D Structure for NP0205179 (4-{4,8-dimethoxy-2h-pyrido[3,4-b]indol-1-yl}-7-methoxy-1h,2h,3h,4h,12h-5λ⁵-indolo[2,3-a]quinolizin-5-ylium)