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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 17:46:54 UTC

Update Date

2023-03-30 17:46:54 UTC

HMDB ID

HMDB0341483

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Amino-3-methyl-9H-pyrido[2,3-b]indole

Description

3-methyl-1H,2H,9H-pyrido[2,3-b]indol-2-imine, also known as mea-alpha-C or mea-α-C, belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). 3-methyl-1H,2H,9H-pyrido[2,3-b]indol-2-imine is a very strong basic compound (based on its pKa). 3-methyl-1H,2H,9H-pyrido[2,3-b]indol-2-imine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 09071422372D          

 15 17  0  0  0  0            999 V2000
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341483

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(NC3=CC=CC=C23)NC1=N

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

> <INCHI_KEY>
IVLCGFRPPGNALI-UHFFFAOYSA-N

> <FORMULA>
C12H11N3

> <MOLECULAR_WEIGHT>
197.2358

> <EXACT_MASS>
197.095297367

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.932789292870513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-1H,2H,9H-pyrido[2,3-b]indol-2-imine

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.193407346

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.859589987001268

> <JCHEM_PKA_STRONGEST_BASIC>
9.647073947601191

> <JCHEM_POLAR_SURFACE_AREA>
51.67

> <JCHEM_REFRACTIVITY>
72.4481

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-1H,9H-pyrido[2,3-b]indol-2-imine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.679   0.130   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.858  -0.695   0.000  0.00  0.00           N+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9                                                       
CONECT    7    1    6   11                                                  
CONECT    8    4    9   10                                                  
CONECT    9    6    8   12                                                  
CONECT   10    5    8   14                                                  
CONECT   11    7   13   15                                                  
CONECT   12    9   14   15                                                  
CONECT   13   11                                                            
CONECT   14   10   12                                                       
CONECT   15   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
MeA-alpha-C	Kegg
MeA-a-C	Generator
MeA-α-C	Generator
MeAalphaC	MeSH
2-a-3-MPI	MeSH
2-amino-3-Methyl-9H-pyrido(2,3-b)indole	MeSH

Chemical Formula

C₁₂H₁₁N₃

Average Molecular Weight

197.2358

Monoisotopic Molecular Weight

197.095297367

IUPAC Name

3-methyl-1H,2H,9H-pyrido[2,3-b]indol-2-imine

Traditional Name

3-methyl-1H,9H-pyrido[2,3-b]indol-2-imine

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(NC3=CC=CC=C23)NC1=N

InChI Identifier

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

InChI Key

IVLCGFRPPGNALI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Alpha carbolines

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridoindole (CHEBI:82337 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Microsome ()
Membrane ()

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nucleotide excision repair ()

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.9	ALOGPS
logP	2.19	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	16.86	ChemAxon
pKa (Strongest Basic)	9.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	51.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.45 m³·mol⁻¹	ChemAxon
Polarizability	21.93 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 10V, Positive-QTOF	splash10-0002-0900000000-ef9275aeb8d36560a645	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 20V, Positive-QTOF	splash10-0002-0900000000-14c2e8dacec9e417a811	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 40V, Positive-QTOF	splash10-001i-0900000000-60a7bd91909c4ec1c513	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 10V, Negative-QTOF	splash10-0002-0900000000-f62d69d9b4756b389e78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 20V, Negative-QTOF	splash10-0002-0900000000-bdd8b79de63705d85a80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-methyl-9H-pyrido[2,3-b]indole 40V, Negative-QTOF	splash10-0kc5-1900000000-538c572382f1501462ce	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19253

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62244

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-Amino-3-methyl-9H-pyrido[2,3-b]indole (HMDB0341483)

MOL for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

3D MOL for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

3D SDF for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

3D-SDF for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

PDB for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

3D PDB for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

SMILES for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

INCHI for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

Structure for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

3D Structure for HMDB0341483 (2-Amino-3-methyl-9H-pyrido[2,3-b]indole)

Predicted Kovats Retention Indices

MS/MS Spectra