NP-MRD: Showing NP-Card for 2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione (NP0283749)

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Record Information

Version

2.0

Created at

2022-09-09 11:08:52 UTC

Updated at

2022-09-09 11:08:52 UTC

NP-MRD ID

NP0283749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione

Description

2-Methyl-6-(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton. 2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione is found in Biflustra perfragilis. 2-Methyl-6-(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517222D          

 16 17  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0283749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=CC(=O)C2=CN(C)C(=O)C=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO3S/c1-12-5-7-6(3-10(12)14)11(15)9(16-2)4-8(7)13/h3-5H,1-2H3

> <INCHI_KEY>
FQUMKAMMIHTWOX-UHFFFAOYSA-N

> <FORMULA>
C11H9NO3S

> <MOLECULAR_WEIGHT>
235.26

> <EXACT_MASS>
235.030314328

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
23.20697784408103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-6-(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.5575397326666668

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.390210241126874

> <JCHEM_POLAR_SURFACE_AREA>
54.45

> <JCHEM_REFRACTIVITY>
64.1076

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.000  -3.080   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-6-(methylsulphanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione	Generator

Chemical Formula

C₁₁H₉NO₃S

Average Mass

235.2600 Da

Monoisotopic Mass

235.03031 Da

IUPAC Name

2-methyl-6-(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione

Traditional Name

2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione

CAS Registry Number

Not Available

SMILES

CSC1=CC(=O)C2=CN(C)C(=O)C=C2C1=O

InChI Identifier

InChI=1S/C11H9NO3S/c1-12-5-7-6(3-10(12)14)11(15)9(16-2)4-8(7)13/h3-5H,1-2H3

InChI Key

FQUMKAMMIHTWOX-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
Biflustra perfragilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinoline quinones

Direct Parent

Isoquinoline quinones

Alternative Parents

Substituents

Isoquinoline quinone
Isoquinolone
Aryl ketone
Pyridinone
Pyridine
Vinylogous thioester
Heteroaromatic compound
Vinylogous amide
Ketone
Lactam
Thioenolether
Azacycle
Sulfenyl compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	0.92	ALOGPS
logP	0.56	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	54.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.11 m³·mol⁻¹	ChemAxon
Polarizability	23.21 Å³	ChemAxon
Number of Rings	2	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

23427448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione (NP0283749)

MOL for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

3D MOL for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

3D SDF for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

3D-SDF for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

PDB for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

3D PDB for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

SMILES for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

INCHI for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

Structure for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)

3D Structure for NP0283749 (2-methyl-6-(methylsulfanyl)isoquinoline-3,5,8-trione)