NP-MRD: Showing NP-Card for 2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole (NP0164053)

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Record Information

Version

2.0

Created at

2022-09-02 22:51:50 UTC

Updated at

2022-09-02 22:51:50 UTC

NP-MRD ID

NP0164053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole

Description

1,2,3,4-Tetrahydro-2-methyl-b-carboline, also known as 2-methyl-1,2,3,4-tetrahydro-beta-carboline or 2-methyltryptoline, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 1,2,3,4-Tetrahydro-2-methyl-b-carboline is a very strong basic compound (based on its pKa). Outside of the human body, 1,2,3,4-Tetrahydro-2-methyl-b-carboline has been detected, but not quantified in, fruits. 2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole is found in Arundo donax, Cyathobasis fruticulosa, Papaver rhoeas, Phalaris aquatica, Phalaris arundinacea and Phalaris coerulescens. This could make 1,2,3,4-tetrahydro-2-methyl-b-carboline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -3.7297    0.6274   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591   -0.3417   -0.1715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -0.3091    1.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -1.0702    1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586   -0.4899    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -0.1358   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    0.3619   -1.6392 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    0.3350   -0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    0.7184   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.5671   -0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8052    0.0324    1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -0.3492    1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5059   -0.2012    0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -0.3300   -1.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    1.2402   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6719    1.3261    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6832    0.0602   -0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -0.8206    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430    0.7061    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -2.1290    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -0.8978    2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428    0.7322   -2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3623    1.1413   -2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1015    0.8773   -0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840   -0.0751    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235   -0.7745    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0713    0.4829   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772   -1.2846   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6 14  1  0
  6  7  1  0
  7  8  1  0
  8 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 14  2  1  0
  9  8  1  0
 13  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
 14 27  1  0
 14 28  1  0
  7 22  1  0
 12 26  1  0
 11 25  1  0
 10 24  1  0
  9 23  1  0
M  END


  Mrv0541 02241215032D          

 14 16  0  0  0  0            999 V2000
    0.4946    1.3196    0.0000 C   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
    0.3296   -0.0821    0.0000 C   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
    1.6496    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    1.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321    1.8971    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
   -0.9896   -0.2471    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
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  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
M  END
> <DATABASE_ID>
NP0164053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=C(C1)NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3

> <INCHI_KEY>
JOFKCNJIUXPJAC-UHFFFAOYSA-N

> <FORMULA>
C12H14N2

> <MOLECULAR_WEIGHT>
186.253

> <EXACT_MASS>
186.115698458

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.969912389360736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.9732942060000003

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.448722090420933

> <JCHEM_PKA_STRONGEST_BASIC>
6.917092080291092

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
58.874300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.923   2.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.001   1.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.615  -0.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.155  -0.307   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.079   0.923   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.463   2.309   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.233   3.541   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      -1.847  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.615  -1.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.615  -2.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.847  -3.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.233  -2.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.233  -1.231   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    3    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,3,4,9-Tetrahydro-2-methyl-1H-pyrido[3,4-b]indole	HMDB
2,3,4,9-Tetrahydro-2-methyl-1H-pyrido[3,4-b]indole, 9ci	HMDB
2-Methyl-1,2,3,4-tetrahydro-beta-carboline	HMDB
2-Methyl-9H-1,2,3,4-tetrahydropyrido(3,4-b) indole	HMDB
2-Methyltryptoline	HMDB
2-Methyltetrahydro-beta-carboline	HMDB

Chemical Formula

C₁₂H₁₄N₂

Average Mass

186.2530 Da

Monoisotopic Mass

186.11570 Da

IUPAC Name

2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

Traditional Name

2-methyl-1H,3H,4H,9H-pyrido[3,4-b]indole

CAS Registry Number

Not Available

SMILES

CN1CCC2=C(C1)NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3

InChI Key

JOFKCNJIUXPJAC-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
Arundo donax	LOTUS Database	35616633
Cyathobasis fruticulosa	LOTUS Database	35616633
Papaver rhoeas	LOTUS Database	35616633
Phalaris aquatica	LOTUS Database	35616633
Phalaris arundinacea	LOTUS Database	35616633
Phalaris coerulescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
3-alkylindole
Indole
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Amine
Organonitrogen compound
Organopnictogen compound
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	1.83	ALOGPS
logP	1.97	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	6.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	58.87 m³·mol⁻¹	ChemAxon
Polarizability	21.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029836

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001051

KNApSAcK ID

Not Available

Chemspider ID

108744

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121896

PDB ID

Not Available

ChEBI ID

213990

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole (NP0164053)

MOL for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

3D MOL for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

3D SDF for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

3D-SDF for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

PDB for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

3D PDB for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

SMILES for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

INCHI for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

Structure for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)

3D Structure for NP0164053 (2-methyl-1h,3h,4h,9h-pyrido[3,4-b]indole)