NP-MRD: Showing NP-Card for 4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole (NP0199568)

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Record Information

Version

2.0

Created at

2022-09-04 18:13:58 UTC

Updated at

2022-09-04 18:13:58 UTC

NP-MRD ID

NP0199568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole

Description

5-Methanesulfinyl-4-({9H-pyrido[3,4-b]indol-9-yl}methyl)-1H-imidazole belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 5-Methanesulfinyl-4-({9H-pyrido[3,4-b]indol-9-yl}methyl)-1H-imidazole is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    4.0045    2.0617    0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594    1.3638   -0.5484 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.7800    1.9060   -1.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6231   -0.3730   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3447   -1.2661   -1.1630 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714   -2.4953   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0390   -2.3708    0.1634 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7888   -1.0456    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -0.6517    1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4784   -0.2194    0.8821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.0266    0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -2.3964    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -3.0220    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8657   -2.2832   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566   -0.9066   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791   -0.3038    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    1.0068    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733    2.1701   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    3.3819    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    3.4284    0.4855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404    2.2909    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    1.0320    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283    1.2994    1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6897    2.7224   -0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    2.7199    1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477   -1.0079   -1.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.4583   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    0.1813    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -1.4517    2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -2.9713    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969   -4.1034    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7975   -2.7325   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5553   -0.2915   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984    2.1463   -0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    4.3130   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513    2.3531    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  2  0
  2  4  1  0
  4  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 16 17  1  0
 17 22  2  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
 22 10  1  0
 12 11  2  0
 18 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  9 28  1  0
  9 29  1  0
 15 33  1  0
 14 32  1  0
 13 31  1  0
 12 30  1  0
 21 36  1  0
 19 35  1  0
 18 34  1  0
  6 27  1  0
  5 26  1  0
M  END


  Mrv1533004161514552D          

 22 25  0  0  0  0            999 V2000
    2.5310    3.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    4.1205    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748    4.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    3.7400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862    3.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658    2.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195    2.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    2.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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
  4  8  2  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  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  2  0  0  0  0
 16 17  1  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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 17 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0199568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)C1=C(CN2C3=C(C=CC=C3)C3=C2C=NC=C3)N=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N4OS/c1-22(21)16-13(18-10-19-16)9-20-14-5-3-2-4-11(14)12-6-7-17-8-15(12)20/h2-8,10H,9H2,1H3,(H,18,19)

> <INCHI_KEY>
NUHYIZQBMKHEAZ-UHFFFAOYSA-N

> <FORMULA>
C16H14N4OS

> <MOLECULAR_WEIGHT>
310.38

> <EXACT_MASS>
310.088832261

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.578843536649178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methanesulfinyl-4-({9H-pyrido[3,4-b]indol-9-yl}methyl)-1H-imidazole

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.6070699596666664

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.446017234842024

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.147351298701203

> <JCHEM_PKA_STRONGEST_BASIC>
5.372556868334987

> <JCHEM_POLAR_SURFACE_AREA>
63.57

> <JCHEM_REFRACTIVITY>
86.87209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3H-imidazole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.724   7.216   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       3.260   7.692   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       2.940   9.198   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.115   6.661   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.609   6.981   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.161   5.648   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.869   4.503   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.276   5.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.610   4.360   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   10   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
5-Methanesulphinyl-4-({9h-pyrido[3,4-b]indol-9-yl}methyl)-1H-imidazole	Generator

Chemical Formula

C₁₆H₁₄N₄OS

Average Mass

310.3800 Da

Monoisotopic Mass

310.08883 Da

IUPAC Name

5-methanesulfinyl-4-({9H-pyrido[3,4-b]indol-9-yl}methyl)-1H-imidazole

Traditional Name

4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3H-imidazole

CAS Registry Number

Not Available

SMILES

CS(=O)C1=C(CN2C3=C(C=CC=C3)C3=C2C=NC=C3)N=CN1

InChI Identifier

InChI=1S/C16H14N4OS/c1-22(21)16-13(18-10-19-16)9-20-14-5-3-2-4-11(14)12-6-7-17-8-15(12)20/h2-8,10H,9H2,1H3,(H,18,19)

InChI Key

NUHYIZQBMKHEAZ-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

Not Available

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
N-alkylindole
Indole
Benzenoid
Substituted pyrrole
Pyridine
Azole
Imidazole
Heteroaromatic compound
Pyrrole
Sulfoxide
Azacycle
Sulfinyl compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	1.4	ALOGPS
logP	0.61	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	5.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.87 m³·mol⁻¹	ChemAxon
Polarizability	31.58 Å³	ChemAxon
Number of Rings	4	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

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

15410361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole (NP0199568)

MOL for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

3D MOL for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

3D SDF for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

3D-SDF for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

PDB for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

3D PDB for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

SMILES for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

INCHI for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

Structure for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)

3D Structure for NP0199568 (4-methanesulfinyl-5-{pyrido[3,4-b]indol-9-ylmethyl}-3h-imidazole)