NP-MRD: Showing NP-Card for 2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione (NP0313205)

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Record Information

Version

2.0

Created at

2022-09-11 10:35:29 UTC

Updated at

2022-09-11 10:35:29 UTC

NP-MRD ID

NP0313205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione

Description

Perfragilin B 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-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione is found in Biflustra perfragilis. Perfragilin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.6331   -2.9062    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508   -1.1406   -0.0402 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832   -0.5167   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    0.7503   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0952    1.8325   -0.6727 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    3.5235   -1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3837    1.2959   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797    2.5182   -0.5918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518    0.4363   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    0.8682   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -0.0019    0.2465 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140    0.5064    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507   -1.2987    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -2.0656    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -1.7700    0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -0.8927    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558   -1.3901    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -2.6167    0.5112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569   -3.3367    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0012   -3.4280   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1411   -3.0307    1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5298   -1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363    4.2049   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    3.9100   -0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459    1.9152   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766    1.5503    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507    0.4473   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839   -0.0823    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -2.8119    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  4  1  0
  9 16  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 15 29  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 10 25  1  0
M  END


  Mrv1533004201505022D          

 18 19  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
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0313205

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO3S2/c1-13-5-7-6(4-8(13)14)9(15)11(17-2)12(18-3)10(7)16/h4-5H,1-3H3

> <INCHI_KEY>
YCRBNFTXGDZHPI-UHFFFAOYSA-N

> <FORMULA>
C12H11NO3S2

> <MOLECULAR_WEIGHT>
281.34

> <EXACT_MASS>
281.018035566

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
28.140677362400083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-6,7-bis(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
0.9394056143333336

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3963164984112972

> <JCHEM_POLAR_SURFACE_AREA>
54.45

> <JCHEM_REFRACTIVITY>
76.85300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-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  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  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   17                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₁NO₃S₂

Average Mass

281.3400 Da

Monoisotopic Mass

281.01804 Da

IUPAC Name

2-methyl-6,7-bis(methylsulfanyl)-2,3,5,8-tetrahydroisoquinoline-3,5,8-trione

Traditional Name

2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione

CAS Registry Number

Not Available

SMILES

CSC1=C(SC)C(=O)C2=CC(=O)N(C)C=C2C1=O

InChI Identifier

InChI=1S/C12H11NO3S2/c1-13-5-7-6(4-8(13)14)9(15)11(17-2)12(18-3)10(7)16/h4-5H,1-3H3

InChI Key

YCRBNFTXGDZHPI-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
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
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	1.52	ALOGPS
logP	0.94	ChemAxon
logS	-2.8	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	2	ChemAxon
Refractivity	76.85 m³·mol⁻¹	ChemAxon
Polarizability	28.14 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

381111

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-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione (NP0313205)

MOL for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

3D MOL for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

3D SDF for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

3D-SDF for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

PDB for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

3D PDB for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

SMILES for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

INCHI for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

Structure for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)

3D Structure for NP0313205 (2-methyl-6,7-bis(methylsulfanyl)isoquinoline-3,5,8-trione)