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Showing NP-Card for 3-Methyl sulfolane (NP0083443)

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Record Information
Version2.0
Created at2022-04-29 04:29:17 UTC
Updated at2022-04-29 04:29:17 UTC
NP-MRD IDNP0083443
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyl sulfolane
DescriptionSulfolane, also known as 1,1-dioxothiolan or (CH2)4SO2, 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. The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides non-polar stability. Sulfolane is possibly neutral. This reaction produces tetramethylene sulfoxide, which can then be further oxidized. This was then hydrogenated using Raney nickel as a catalyst to give sulfolane. Because sulfolane is one of the most efficient industrial solvents for purifying aromatics, the process operates at a relatively low solvent-to-feed ratio, making sulfolane relatively cost effective compared to similar-purpose solvents. 3-Methyl sulfolane is found in Homo sapiens (Urine). 3-Methyl sulfolane was first documented in 1985 (PMID: 4071560). It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions (PMID: 11878596) (PMID: 22219044) (PMID: 22918536) (PMID: 22936336) (PMID: 3709502).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083443 (3-Methyl sulfolane)


  Mrv1533004171519322D          

  7  7  0  0  0  0            999 V2000
    1.1198    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   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 C   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
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  2  7  1  0  0  0  0
M  END
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3D MOL for NP0083443 (3-Methyl sulfolane)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.2665   -1.0983    1.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.6183    0.0393 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.6409   -0.7706   -1.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7801    1.0772    0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    1.0668   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.2392   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536   -1.3027    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5211    1.7338   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7822    1.3064    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4459    1.4676   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2011    1.8312    0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596   -0.2065    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267   -0.5603   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380   -1.4091    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -2.2778   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  4  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
M  END
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3D SDF for NP0083443 (3-Methyl sulfolane)


  Mrv1533004171519322D          

  7  7  0  0  0  0            999 V2000
    1.1198    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 O   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 C   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
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=S1(=O)CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2

> <INCHI_KEY>
HXJUTPCZVOIRIF-UHFFFAOYSA-N

> <FORMULA>
C4H8O2S

> <MOLECULAR_WEIGHT>
120.17

> <EXACT_MASS>
120.024500672

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.477256062199565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1λ⁶-thiolane-1,1-dione

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.5907958413333335

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
27.907999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfolane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0083443 (3-Methyl sulfolane)

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PDB for NP0083443 (3-Methyl sulfolane)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       2.090   3.224   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0       1.060   2.080   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       0.029   3.224   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0083443 (3-Methyl sulfolane)
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SMILES for NP0083443 (3-Methyl sulfolane)
O=S1(=O)CCCC1
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INCHI for NP0083443 (3-Methyl sulfolane)
InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
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View in JSmol
Synonyms
ValueSource
(CH2)4SO2ChEBI
1,1-DioxidetetrahydrothiofuranChEBI
1,1-DioxidetetrahydrothiopheneChEBI
1,1-DioxothiolanChEBI
2,3,4,5-Tetrahydrothiophene-1,1-dioxideChEBI
Cyclic tetramethylene sulfoneChEBI
Cyclotetramethylene sulfoneChEBI
DioxothiolanChEBI
SulfolanChEBI
Tetrahydrothiophene 1-dioxideChEBI
Tetramethylene sulfoneChEBI
Thiacyclopentane dioxideChEBI
Thiolane-1,1-dioxideChEBI
Thiophan sulfoneChEBI
Thiophane dioxideChEBI
Cyclic tetramethylene sulphoneGenerator
Cyclotetramethylene sulphoneGenerator
SulpholanGenerator
Tetramethylene sulphoneGenerator
Thiophan sulphoneGenerator
SulpholaneGenerator
Chemical FormulaC4H8O2S
Average Mass120.1700 Da
Monoisotopic Mass120.02450 Da
IUPAC Name1λ⁶-thiolane-1,1-dione
Traditional Namesulfolane
CAS Registry NumberNot Available
SMILES
O=S1(=O)CCCC1
InChI Identifier
InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
InChI KeyHXJUTPCZVOIRIF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Homo sapiens (Urine)Animalia
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
  • Thiolane
    • 

  • Sulfone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP-0.65ALOGPS
logP-0.59ChemAxon
logS-0.36ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.91 m³·mol⁻¹ChemAxon
Polarizability11.48 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-3747  
BiGG IDNot Available
Wikipedia LinkSulfolane  
METLIN IDNot Available
PubChem Compound31347  
PDB IDNot Available
ChEBI ID74794  
Good Scents IDNot Available
References
General References
  1. Headley JV, Fedorak PM, Dickson LC: A review of analytical methods for the determination of sulfolane and alkanolamines in environmental studies. J AOAC Int. 2002 Jan-Feb;85(1):154-62. [PubMed:11878596  ] 
  2. Douglass KA, Venter AR: Investigating the role of adducts in protein supercharging with sulfolane. J Am Soc Mass Spectrom. 2012 Mar;23(3):489-97. doi: 10.1007/s13361-011-0319-1. Epub 2012 Jan 5. [PubMed:22219044  ] 
  3. Versace F, Uppugunduri CR, Krajinovic M, Theoret Y, Gumy-Pause F, Mangin P, Staub C, Ansari M: A novel method for quantification of sulfolane (a metabolite of busulfan) in plasma by gas chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2012 Oct;404(6-7):1831-8. doi: 10.1007/s00216-012-6330-y. Epub 2012 Aug 24. [PubMed:22918536  ] 
  4. Thompson CM, Gaylor DW, Tachovsky JA, Perry C, Carakostas MC, Haws LC: Development of a chronic noncancer oral reference dose and drinking water screening level for sulfolane using benchmark dose modeling. J Appl Toxicol. 2013 Dec;33(12):1395-406. doi: 10.1002/jat.2799. Epub 2012 Aug 31. [PubMed:22936336  ] 
  5. Gordon CJ, Long MD, Fehlner KS, Dyer RS: Sulfolane-induced hypothermia enhances survivability in mice. Environ Res. 1986 Jun;40(1):92-7. doi: 10.1016/s0013-9351(86)80084-6. [PubMed:3709502  ] 
  6. Ruppert PH, Dyer RS: Acute behavioral toxicity of sulfolane: influence of hypothermia. Toxicol Lett. 1985 Nov;28(2-3):111-6. doi: 10.1016/0378-4274(85)90018-9. [PubMed:4071560  ]