NP-MRD: Showing NP-Card for Methyl troposulfenin (NP0019507)

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Record Information

Version

2.0

Created at

2021-01-06 05:00:28 UTC

Updated at

2021-07-15 17:31:09 UTC

NP-MRD ID

NP0019507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl troposulfenin

Provided By

NPAtlas

Description

Methyl troposulfenin is found in Phaeobacter inhibens. Methyl troposulfenin was first documented in 2019 (PMID: 30978024). Based on a literature review very few articles have been published on 8-(methylsulfanyl)-3H,4H-cyclohepta[c][1,2]oxathiole-3,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120173D          

 20 21  0  0  0  0            999 V2000
    3.5436   -0.7490   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9572   -1.5621   -0.3272 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.3815   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    0.9626   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    1.9983    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    1.9219    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311    0.8654    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358    1.1952    0.1205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.5154    0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483   -1.4159    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0924   -1.1120    0.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381   -2.6772    0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983   -2.6962    0.0715 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005   -1.0143    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935    0.1205   -1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2628   -1.4664   -0.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -0.4808    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400    1.1748   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995    3.0003    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901    2.8318    0.8775 H   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  3  1  0  0  0  0
 14  9  2  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0019507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(=O)C2=C(SOC2=O)C(SC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O3S2/c1-13-6-4-2-3-5(10)7-8(6)14-12-9(7)11/h2-4H,1H3

> <INCHI_KEY>
BMECXPFQKLRLQJ-UHFFFAOYSA-N

> <FORMULA>
C9H6O3S2

> <MOLECULAR_WEIGHT>
226.26

> <EXACT_MASS>
225.975836401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
21.494609218242317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(methylsulfanyl)-3H,4H-cyclohepta[c][1,2]oxathiole-3,4-dione

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.7526316596666667

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.113365050014629

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
61.08980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(methylsulfanyl)cyclohepta[c][1,2]oxathiole-3,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.544  -0.749  -0.542  0.00  0.00           C+0
HETATM    2  S   UNK     0       1.957  -1.562  -0.327  0.00  0.00           S+0
HETATM    3  C   UNK     0       0.633  -0.382  -0.129  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.926   0.963  -0.156  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.062   1.998   0.113  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.264   1.922   0.427  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.131   0.865   0.257  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.336   1.195   0.121  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.866  -0.515   0.214  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.848  -1.416   0.345  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.092  -1.112   0.517  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.538  -2.677   0.297  0.00  0.00           O+0
HETATM   13  S   UNK     0      -0.898  -2.696   0.072  0.00  0.00           S+0
HETATM   14  C   UNK     0      -0.601  -1.014   0.038  0.00  0.00           C+0
HETATM   15  H   UNK     0       3.494   0.121  -1.228  0.00  0.00           H+0
HETATM   16  H   UNK     0       4.263  -1.466  -0.998  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.946  -0.481   0.453  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.940   1.175  -0.417  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.500   3.000   0.067  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.690   2.832   0.878  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3    9                                                  
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
8-(Methylsulphanyl)-3H,4H-cyclohepta[c][1,2]oxathiole-3,4-dione	Generator
Methyl troposulphenin	Generator

Chemical Formula

C₉H₆O₃S₂

Average Mass

226.2600 Da

Monoisotopic Mass

225.97584 Da

IUPAC Name

8-(methylsulfanyl)-3H,4H-cyclohepta[c][1,2]oxathiole-3,4-dione

Traditional Name

8-(methylsulfanyl)cyclohepta[c][1,2]oxathiole-3,4-dione

CAS Registry Number

Not Available

SMILES

CSC1=CC=CC(=O)C2=C1SOC2=O

InChI Identifier

InChI=1S/C9H6O3S2/c1-13-6-4-2-3-5(10)7-8(6)14-12-9(7)11/h2-4H,1H3

InChI Key

BMECXPFQKLRLQJ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Phaeobacter inhibens	NPAtlas	30978024

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tropones. These are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Not Available

Direct Parent

Tropones

Alternative Parents

Substituents

Aryl thioether
Tropone
Alkylarylthioether
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Organic oxygen compound
Organic oxide
Organosulfur compound
Organooxygen 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	1.85	ALOGPS
logP	1.75	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.09 m³·mol⁻¹	ChemAxon
Polarizability	21.49 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

NPAtlas ID

NPA025179

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

75320563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145720948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Phippen CBW, Jorgensen CM, Bentzon-Tilia M, Gotfredsen CH, Larsen TO, Gram L, Sonnenschein EC: Isolation of Methyl Troposulfenin from Phaeobacter inhibens. J Nat Prod. 2019 May 24;82(5):1387-1390. doi: 10.1021/acs.jnatprod.8b01097. Epub 2019 Apr 12. [PubMed:30978024 ]

Showing NP-Card for Methyl troposulfenin (NP0019507)

MOL for NP0019507 (Methyl troposulfenin)

3D MOL for NP0019507 (Methyl troposulfenin)

3D SDF for NP0019507 (Methyl troposulfenin)

3D-SDF for NP0019507 (Methyl troposulfenin)

PDB for NP0019507 (Methyl troposulfenin)

3D PDB for NP0019507 (Methyl troposulfenin)

SMILES for NP0019507 (Methyl troposulfenin)

INCHI for NP0019507 (Methyl troposulfenin)

Structure for NP0019507 (Methyl troposulfenin)

3D Structure for NP0019507 (Methyl troposulfenin)