NP-MRD: Showing NP-Card for 6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione (NP0227678)

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Record Information

Version

2.0

Created at

2022-09-06 07:04:50 UTC

Updated at

2022-09-06 07:04:50 UTC

NP-MRD ID

NP0227678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione

Description

6-(2-{4,8-Dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione is found in Picrasma quassioides. 6-(2-{4,8-Dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506392D          

 37 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004201506392D          

 37 43  0  0  0  0            999 V2000
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 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
 26 31  1  0  0  0  0
 11 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
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
  7 37  1  0  0  0  0
 10 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0227678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1NC1=C2C(OC)=CN=C1CCN1C=CC2=C3N(C4=CC=CC=C24)C(=O)C(=O)C=C13

> <INCHI_IDENTIFIER>
InChI=1S/C29H22N4O4/c1-36-23-9-5-7-18-25-24(37-2)15-30-19(27(25)31-26(18)23)11-13-32-12-10-17-16-6-3-4-8-20(16)33-28(17)21(32)14-22(34)29(33)35/h3-10,12,14-15,31H,11,13H2,1-2H3

> <INCHI_KEY>
RXCDWRJHTVZARX-UHFFFAOYSA-N

> <FORMULA>
C29H22N4O4

> <MOLECULAR_WEIGHT>
490.519

> <EXACT_MASS>
490.164105204

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
52.66049175938298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(2-{4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
3.0842079326666685

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.0622815125248

> <JCHEM_PKA_STRONGEST_BASIC>
5.093052132549562

> <JCHEM_POLAR_SURFACE_AREA>
89.45

> <JCHEM_REFRACTIVITY>
139.99179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-{4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.237   5.942   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.398   4.410   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.805   3.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.051   4.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.457   4.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.618   2.531   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.373   1.626   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.966   2.253   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.935   1.108   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -5.705  -0.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.229  -1.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.723  -2.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.693  -0.866   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.186  -1.186   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.710  -2.651   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.796  -2.971   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.827  -1.827   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.351  -0.362   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.156  -0.042   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.217   1.796   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.029   2.701   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.868   4.233   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.436   2.075   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.681   2.980   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       2.597   0.543   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.842  -0.362   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.349  -0.042   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.379  -1.186   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.903  -2.651   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.397  -2.971   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.367  -1.827   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -6.260  -2.835   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -7.766  -2.514   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.242  -1.050   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -9.748  -0.730   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.224   0.735   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.212   0.095   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   37                                                  
CONECT   11   10   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   17   26                                                  
CONECT   32   11   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34    7   10                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₂N₄O₄

Average Mass

490.5190 Da

Monoisotopic Mass

490.16411 Da

IUPAC Name

6-(2-{4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione

Traditional Name

6-(2-{4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10,12,14-hexaene-2,3-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1NC1=C2C(OC)=CN=C1CCN1C=CC2=C3N(C4=CC=CC=C24)C(=O)C(=O)C=C13

InChI Identifier

InChI=1S/C29H22N4O4/c1-36-23-9-5-7-18-25-24(37-2)15-30-19(27(25)31-26(18)23)11-13-32-12-10-17-16-6-3-4-8-20(16)33-28(17)21(32)14-22(34)29(33)35/h3-10,12,14-15,31H,11,13H2,1-2H3

InChI Key

RXCDWRJHTVZARX-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
Picrasma quassioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Harman
Beta-carboline
Pyridoindole
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Anisole
Phenol ether
Alkyl aryl ether
Pyridinone
Benzenoid
Pyridine
Vinylogous amide
Pyrrole
Heteroaromatic compound
Cyclic ketone
Lactam
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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
logP	4.21	ALOGPS
logP	3.08	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	11.06	ChemAxon
pKa (Strongest Basic)	5.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.99 m³·mol⁻¹	ChemAxon
Polarizability	52.66 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione (NP0227678)

MOL for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

3D MOL for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

3D SDF for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

3D-SDF for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

PDB for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

3D PDB for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

SMILES for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

INCHI for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

Structure for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)

3D Structure for NP0227678 (6-(2-{4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl}ethyl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione)