NP-MRD: Showing NP-Card for 1-(3-propylphenyl)-9h-pyrido[3,4-b]indole (NP0184741)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 23:56:36 UTC

Updated at

2022-09-03 23:56:36 UTC

NP-MRD ID

NP0184741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3-propylphenyl)-9h-pyrido[3,4-b]indole

Description

1-(3-Propylphenyl)-9H-pyrido[3,4-b]indole 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-(3-propylphenyl)-9h-pyrido[3,4-b]indole is found in Nitraria komarovii. 1-(3-Propylphenyl)-9H-pyrido[3,4-b]indole is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241514242D          

 22 25  0  0  0  0            999 V2000
    1.8579   -6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059   -6.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -5.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088   -4.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018   -5.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -4.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -3.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 14 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0184741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC=CC(=C1)C1=NC=CC2=C1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N2/c1-2-6-14-7-5-8-15(13-14)19-20-17(11-12-21-19)16-9-3-4-10-18(16)22-20/h3-5,7-13,22H,2,6H2,1H3

> <INCHI_KEY>
WISHAHVIQZDSHU-UHFFFAOYSA-N

> <FORMULA>
C20H18N2

> <MOLECULAR_WEIGHT>
286.378

> <EXACT_MASS>
286.146998588

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.63146326042806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3-propylphenyl)-9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.308847669333334

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.157042797879555

> <JCHEM_PKA_STRONGEST_BASIC>
4.709614034124519

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
90.32270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-propylphenyl)-9H-pyrido[3,4-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.468 -12.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.438 -11.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.914 -10.366   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.883  -9.222   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.377  -9.542   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.654  -8.397   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.178  -6.933   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.328  -6.612   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.359  -7.757   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.774  -4.003   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   22  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                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   10   14                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈N₂

Average Mass

286.3780 Da

Monoisotopic Mass

286.14700 Da

IUPAC Name

1-(3-propylphenyl)-9H-pyrido[3,4-b]indole

Traditional Name

1-(3-propylphenyl)-9H-pyrido[3,4-b]indole

CAS Registry Number

Not Available

SMILES

CCCC1=CC=CC(=C1)C1=NC=CC2=C1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C20H18N2/c1-2-6-14-7-5-8-15(13-14)19-20-17(11-12-21-19)16-9-3-4-10-18(16)22-20/h3-5,7-13,22H,2,6H2,1H3

InChI Key

WISHAHVIQZDSHU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nitraria komarovii	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
2-phenylpyridine
Indole
Indole or derivatives
Phenylpropane
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen 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	5.73	ALOGPS
logP	5.31	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	4.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	33.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11077007

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3-propylphenyl)-9h-pyrido[3,4-b]indole (NP0184741)

MOL for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

3D MOL for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

3D SDF for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

3D-SDF for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

PDB for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

3D PDB for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

SMILES for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

INCHI for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

Structure for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)

3D Structure for NP0184741 (1-(3-propylphenyl)-9h-pyrido[3,4-b]indole)