NP-MRD: Showing NP-Card for 1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione (NP0230111)

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Record Information

Version

2.0

Created at

2022-09-06 10:27:31 UTC

Updated at

2022-09-06 10:27:31 UTC

NP-MRD ID

NP0230111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione

Description

1,4-Bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-dione 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. 1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione is found in Picrasma quassioides. 1,4-Bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-dione is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506262D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201506262D          

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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 14 17  1  0  0  0  0
  7 17  1  0  0  0  0
 10 17  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 31 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 24 40  1  0  0  0  0
 30 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0230111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1NC1=C2C(OC)=CN=C1C(=O)CCC(=O)C1=NC=C(OC)C2=C1NC1=C2C=CC=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H26N4O6/c1-37-19-9-5-7-15-23-21(39-3)13-31-27(29(23)33-25(15)19)17(35)11-12-18(36)28-30-24(22(40-4)14-32-28)16-8-6-10-20(38-2)26(16)34-30/h5-10,13-14,33-34H,11-12H2,1-4H3

> <INCHI_KEY>
LOAYVFVYPWFISK-UHFFFAOYSA-N

> <FORMULA>
C30H26N4O6

> <MOLECULAR_WEIGHT>
538.56

> <EXACT_MASS>
538.185234573

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
56.720417217332795

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-dione

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.050945611999999

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.769016765546615

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.166957199347042

> <JCHEM_PKA_STRONGEST_BASIC>
3.78734030183862

> <JCHEM_POLAR_SURFACE_AREA>
128.42000000000002

> <JCHEM_REFRACTIVITY>
146.79459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-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     -10.123  -8.397   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.616  -8.717   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.140 -10.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.171 -11.327   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.695 -12.791   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.189 -13.111   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.158 -11.967   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.634 -10.502   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -5.388  -9.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.142 -10.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.636 -10.182   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.606 -11.327   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.081 -12.791   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.588 -13.111   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.064 -14.576   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.570 -14.896   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.618 -11.967   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.160  -8.717   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.191  -7.573   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.654  -8.397   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.178  -6.933   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.328  -6.612   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.359  -7.757   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       0.774  -4.003   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.232  -0.754   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.738  -0.434   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.785  -6.612   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.291  -6.933   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0       3.311  -4.828   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   17                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    7   10                                                  
CONECT   18   11   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   40                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   40                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   31   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   24   30                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆N₄O₆

Average Mass

538.5600 Da

Monoisotopic Mass

538.18523 Da

IUPAC Name

1,4-bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-dione

Traditional Name

1,4-bis({4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl})butane-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1NC1=C2C(OC)=CN=C1C(=O)CCC(=O)C1=NC=C(OC)C2=C1NC1=C2C=CC=C1OC

InChI Identifier

InChI=1S/C30H26N4O6/c1-37-19-9-5-7-15-23-21(39-3)13-31-27(29(23)33-25(15)19)17(35)11-12-18(36)28-30-24(22(40-4)14-32-28)16-8-6-10-20(38-2)26(16)34-30/h5-10,13-14,33-34H,11-12H2,1-4H3

InChI Key

LOAYVFVYPWFISK-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 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
Indole
Indole or derivatives
Aryl alkyl ketone
Aryl ketone
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Pyridine
Vinylogous amide
Pyrrole
Heteroaromatic compound
Ketone
Azacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organic oxide
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	3.69	ALOGPS
logP	3.05	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	3.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.42 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.79 m³·mol⁻¹	ChemAxon
Polarizability	56.72 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

21637696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione (NP0230111)

MOL for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

3D MOL for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

3D SDF for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

3D-SDF for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

PDB for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

3D PDB for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

SMILES for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

INCHI for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

Structure for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)

3D Structure for NP0230111 (1,4-bis({4,8-dimethoxy-9h-pyrido[3,4-b]indol-1-yl})butane-1,4-dione)