Np mrd loader

Showing NP-Card for gamma-thiobutyrolactone (NP0201418)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-04 20:27:42 UTC
Updated at2022-09-04 20:27:42 UTC
NP-MRD IDNP0201418
Secondary Accession NumbersNone
Natural Product Identification
Common Namegamma-thiobutyrolactone
DescriptionDihydro-2(3H)-thiophenone, also known as 2-oxothiolane or 4-butyrothiolactone, belongs to the class of organic compounds known as thiolanes. These are organic compounds containing thiolane, a five-member saturated ring containing four carbon atoms and a sulfur atom. Dihydro-2(3H)-thiophenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydro-2(3H)-thiophenone is a burnt and garlic tasting compound. Outside of the human body, Dihydro-2(3H)-thiophenone has been detected, but not quantified in, coffee and coffee products. gamma-thiobutyrolactone is found in Coffea arabica. This could make dihydro-2(3H)-thiophenone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0201418 (gamma-thiobutyrolactone)


  Mrv0541 05061305502D          

  6  6  0  0  0  0            999 V2000
    0.9803   -0.1553    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
    0.1553   -0.1553    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
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
Download

3D MOL for NP0201418 (gamma-thiobutyrolactone)

     RDKit          3D

 12 12  0  0  0  0  0  0  0  0999 V2000
    2.4550   -0.7192   -0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.4662   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987    0.7802   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.2810    0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860   -0.5636    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -1.5131   -1.0036 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0450    1.1563   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    1.5247    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694    1.1278    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -0.3940    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8040   -1.2706    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400    0.0566   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
M  END
Download

3D SDF for NP0201418 (gamma-thiobutyrolactone)


  Mrv0541 05061305502D          

  6  6  0  0  0  0            999 V2000
    0.9803   -0.1553    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
    0.1553   -0.1553    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
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCCS1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6OS/c5-4-2-1-3-6-4/h1-3H2

> <INCHI_KEY>
KMSNYNIWEORQDJ-UHFFFAOYSA-N

> <FORMULA>
C4H6OS

> <MOLECULAR_WEIGHT>
102.155

> <EXACT_MASS>
102.013935504

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.121710686655746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
thiolan-2-one

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.8004028483333332

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.053860639169298

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
26.653

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-thiobutyrolactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0201418 (gamma-thiobutyrolactone)

Download
PDB for NP0201418 (gamma-thiobutyrolactone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   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  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    6  S   UNK     0      -0.186   1.175   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

Download
3D PDB for NP0201418 (gamma-thiobutyrolactone)
Download
SMILES for NP0201418 (gamma-thiobutyrolactone)
O=C1CCCS1
Download
INCHI for NP0201418 (gamma-thiobutyrolactone)
InChI=1S/C4H6OS/c5-4-2-1-3-6-4/h1-3H2
Download
View in JSmol
Synonyms
ValueSource
2-OxothiolaneHMDB
2-ThiolanoneHMDB
4-ButyrothiolactoneHMDB
4-Mercaptobutanoic acid g-thiolactoneHMDB
4-ThiobutyrolactoneHMDB
Dihydro-2-(3H)-thiophenoneHMDB
g-ThiobutyrolactoneHMDB
gamma-ThiobutyrolactoneHMDB
Laquo gammaraquo -thiobutyrolactoneHMDB
Tetrahydro-2-thiophenoneHMDB
Thiacyclopentan-2-oneHMDB
Thiacyclopentanone-2HMDB
Thiolan-2-oneHMDB
Dihydro-2(3H)-thiophenoneMeSH
Chemical FormulaC4H6OS
Average Mass102.1550 Da
Monoisotopic Mass102.01394 Da
IUPAC Namethiolan-2-one
Traditional Namegamma-thiobutyrolactone
CAS Registry NumberNot Available
SMILES
O=C1CCCS1
InChI Identifier
InChI=1S/C4H6OS/c5-4-2-1-3-6-4/h1-3H2
InChI KeyKMSNYNIWEORQDJ-UHFFFAOYSA-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
Coffea arabicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiolanes. These are organic compounds containing thiolane, a five-member saturated ring containing four carbon atoms and a sulfur atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassThiolanes  
Sub ClassNot Available
Direct ParentThiolanes  
Alternative Parents
Substituents
  • Carbothioic s-lactone
    • 

  • Thiolane
    • 

  • Thiolactone
    • 

  • Thiocarboxylic acid ester
    • 

  • Thiocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.58ALOGPS
logP0.8ChemAxon
logS-0.42ALOGPS
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.65 m³·mol⁻¹ChemAxon
Polarizability10.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031253  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003286  
KNApSAcK IDNot Available
Chemspider ID13252  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13852  
PDB IDNot Available
ChEBI ID187055  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]