NP-MRD: Showing NP-Card for 3-Amino-1-methyl-5H-pyrido[4,3-b]indole (NP0336685)

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Record Information

Version

2.0

Created at

2024-09-11 07:24:23 UTC

Updated at

2024-09-11 07:24:23 UTC

NP-MRD ID

NP0336685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Amino-1-methyl-5H-pyrido[4,3-b]indole

Description

3-Amino-1-methyl-5H-pyrido[4,3-b]indole, also known as 1-methyl-5H-pyrido(4,3-b)indol-3-amine or RP-p-2, belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole. 3-Amino-1-methyl-5H-pyrido[4,3-b]indole is a very strong basic compound (based on its pKa). 3-Amino-1-methyl-5H-pyrido[4,3-b]indole is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214492D          

 15 17  0  0  0  0            999 V2000
    0.3296   -0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.5771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    1.8971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6496    0.4946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  1 14  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=NC(N)=CC2=C1C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C12H11N3/c1-7-12-8-4-2-3-5-9(8)15-10(12)6-11(13)14-7/h2-6,15H,1H3,(H2,13,14)

> <INCHI_KEY>
LKKMLIBUAXYLOY-UHFFFAOYSA-N

> <FORMULA>
C12H11N3

> <MOLECULAR_WEIGHT>
197.2358

> <EXACT_MASS>
197.095297367

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.81653482684974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-5H-pyrido[4,3-b]indol-3-amine

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.7701150073333332

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.09048202560929

> <JCHEM_PKA_STRONGEST_BASIC>
9.68837166303382

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
60.92069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-5H-pyrido[4,3-b]indol-3-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.615  -0.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.615  -1.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -2.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.847  -3.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.233  -2.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.233  -1.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.847  -0.461   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.539   1.077   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.001   1.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.769   2.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.463   2.309   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.233   3.541   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.079   0.923   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.155  -0.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.771  -1.693   0.000  0.00  0.00           C+0
CONECT    1    2    9   14                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14    1   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
1-Methyl-3-amino-5H-pyrido(4,3-b)indole	HMDB
1-Methyl-5H-pyrido(4,3-b)indol-3-amine	HMDB
1-Methyl-5H-pyrido[3,4-b]indol-1-amine, 9ci	HMDB
1-Methyl-5H-pyrido[4,3-b]indol-3-amine	HMDB
1-Methyl-9H-pyrido(4,3-b)indol-3-amine	HMDB
3-Amino-1-methyl-5H-pyrido(4,3-b)indole	HMDB
3-Amino-1-methyl-gamma-carboline	HMDB
RP-p-2	HMDB
TRP-2	HMDB
TRP-p-2	HMDB
TRP-P2	HMDB
Tryptophan P2	HMDB
Tryptophan pyrolysis product II	HMDB
Tryptophan-p-2	HMDB
Trytophan pyrolysate 2	HMDB
Tryptophan pyrolysate	HMDB
Tryptophan pyrolysis product 2	HMDB
3-Amino-1-methyl-5H-pyrido[4,3-b]indole	KEGG

Chemical Formula

C₁₂H₁₁N₃

Average Mass

197.2358 Da

Monoisotopic Mass

197.09530 Da

IUPAC Name

1-methyl-5H-pyrido[4,3-b]indol-3-amine

Traditional Name

1-methyl-5H-pyrido[4,3-b]indol-3-amine

CAS Registry Number

Not Available

SMILES

CC1=NC(N)=CC2=C1C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C12H11N3/c1-7-12-8-4-2-3-5-9(8)15-10(12)6-11(13)14-7/h2-6,15H,1H3,(H2,13,14)

InChI Key

LKKMLIBUAXYLOY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Gamma carbolines

Alternative Parents

Substituents

Gamma-carboline
Indole
Pyrrolopyridine
Aminopyridine
Methylpyridine
Imidolactam
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Azacycle
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridoindole (CHEBI:34328 )

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	2.46	ALOGPS
logP	1.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.92 m³·mol⁻¹	ChemAxon
Polarizability	21.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033188

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011200

KNApSAcK ID

Not Available

Chemspider ID

4447540

KEGG Compound ID

C14416

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5284476

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-Amino-1-methyl-5H-pyrido[4,3-b]indole (NP0336685)

MOL for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

3D MOL for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

3D SDF for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

3D-SDF for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

PDB for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

3D PDB for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

SMILES for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

INCHI for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

Structure for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)

3D Structure for NP0336685 (3-Amino-1-methyl-5H-pyrido[4,3-b]indole)