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Showing NP-Card for (3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol (NP0196677)

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Record Information
Version2.0
Created at2022-09-04 14:48:20 UTC
Updated at2022-09-04 14:48:20 UTC
NP-MRD IDNP0196677
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol
DescriptionRaphanusanin belongs to the class of organic compounds known as thiolactams. These are cyclic thioamides, obtained by replacing the oxygen atom from a lactam ring with sulfur. (3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol is found in Raphanus sativus. (3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol was first documented in 2008 (PMID: 18952246). Based on a literature review a small amount of articles have been published on Raphanusanin (PMID: 24923677) (PMID: 20553608).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)


  Mrv1652309042216482D          

  9  9  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 S   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.5673   -0.1792   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038   -0.9210    0.0820 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.2766   -0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5630    0.1076   -0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -1.0144    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665   -1.0210    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051    0.3276   -0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    0.9437   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426    2.6151   -1.1382 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -0.9478   -0.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    0.3820    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.5593   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    1.1416   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441   -0.8181    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -1.9783    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -1.1472    1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247   -1.7816   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9576    3.4551   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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3D SDF for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)


  Mrv1652309042216482D          

  9  9  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 S   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C1/CCN=C1S

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NS2/c1-9-4-5-2-3-7-6(5)8/h4H,2-3H2,1H3,(H,7,8)/b5-4+

> <INCHI_KEY>
BVYUPEKENRMVJK-SNAWJCMRSA-N

> <FORMULA>
C6H9NS2

> <MOLECULAR_WEIGHT>
159.27

> <EXACT_MASS>
159.017641642

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
16.905087802650115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E)-4-[(methylsulfanyl)methylidene]-3,4-dihydro-2H-pyrrole-5-thiol

> <JCHEM_LOGP>
1.0995938944133756

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.848430853899587

> <JCHEM_PKA_STRONGEST_BASIC>
5.653367363849094

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
46.1336

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)

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PDB for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       2.393   4.390   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0      -1.651   1.651   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)
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SMILES for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)
CS\C=C1/CCN=C1S
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INCHI for NP0196677 ((3e)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol)
InChI=1S/C6H9NS2/c1-9-4-5-2-3-7-6(5)8/h4H,2-3H2,1H3,(H,7,8)/b5-4+
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Synonyms
ValueSource
3-(Methylthio)methylene-2-pyrrolidinethioneMeSH
Chemical FormulaC6H9NS2
Average Mass159.2700 Da
Monoisotopic Mass159.01764 Da
IUPAC Name(4E)-4-[(methylsulfanyl)methylidene]-3,4-dihydro-2H-pyrrole-5-thiol
Traditional Name(3E)-3-[(methylsulfanyl)methylidene]-4,5-dihydropyrrole-2-thiol
CAS Registry NumberNot Available
SMILES
CS\C=C1/CCN=C1S
InChI Identifier
InChI=1S/C6H9NS2/c1-9-4-5-2-3-7-6(5)8/h4H,2-3H2,1H3,(H,7,8)/b5-4+
InChI KeyBVYUPEKENRMVJK-SNAWJCMRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Raphanus sativusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiolactams. These are cyclic thioamides, obtained by replacing the oxygen atom from a lactam ring with sulfur.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassThiolactams  
Sub ClassNot Available
Direct ParentThiolactams  
Alternative Parents
Substituents
  • Thiolactam
    • 

  • Pyrrolidine
    • 

  • Thioenolether
    • 

  • Azacycle
    • 

  • Sulfenyl compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Thiocarbonyl group
    • 

  • Organosulfur compound
    • 

  • Organonitrogen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.1ChemAxon
pKa (Strongest Acidic)6.85ChemAxon
pKa (Strongest Basic)5.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.13 m³·mol⁻¹ChemAxon
Polarizability16.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000309  
Chemspider ID8165093  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9989511  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Moehninsi, Miura K, Yamada K, Shigemori H: Raphanusanin-mediated resistance to pathogens is light dependent in radish and Arabidopsis thaliana. Planta. 2014 Sep;240(3):513-24. doi: 10.1007/s00425-014-2103-5. Epub 2014 Jun 13. [PubMed:24923677  ] 
  2. Moehninsi, Miura K, Nakajyo H, Yamada K, Hasegawa K, Shigemori H: Comparative transcriptional profiling-based identification of raphanusanin-inducible genes. BMC Plant Biol. 2010 Jun 16;10:111. doi: 10.1186/1471-2229-10-111. [PubMed:20553608  ] 
  3. Moehninsi, Yamada K, Hasegawa T, Shigemori H: Raphanusanin-induced genes and the characterization of RsCSN3, a raphanusanin-induced gene in etiolated radish hypocotyls. Phytochemistry. 2008 Nov;69(16):2781-92. doi: 10.1016/j.phytochem.2008.09.014.  Epub 2008 Oct 24. [PubMed:18952246  ] 
  4. LOTUS database [Link]