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Showing metabocard for (S)-Methylbutanethioic acid (HMDB0061879)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-10-08 15:56:28 UTC
Update Date2023-02-21 17:30:32 UTC
HMDB IDHMDB0061879
Secondary Accession Numbers
  • HMDB61879
Metabolite Identification
Common Name(S)-Methylbutanethioic acid
Description(S)-Methylbutanethioic acid belongs to the class of organic compounds known as carbothioic S-acids. These are organic acids with the general formula RCS-OH (R=H, organic group).
Structure
Data?1677000632
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061879 ((S)-Methylbutanethioic acid)


  Mrv1652310012003002D          

  7  6  0  0  0  0            999 V2000
10004.439210004.2128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.723910004.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.154410004.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.439210003.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.723910005.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.008710004.2128    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.868610004.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0061879 ((S)-Methylbutanethioic acid)

HMDB0061879
     RDKit          3D
(S)-Methylbutanethioic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.8529   -0.1979    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -0.3193   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    0.1808   -0.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5594    1.6410    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -0.6476    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.1695    2.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3792    0.6821 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9414    0.7763    0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.9935    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665   -0.3264   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    0.2592   -1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -1.3653   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.0958   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0413    2.1970   -0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    1.7751    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136    1.9911    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -2.5176   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  6
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
Download

3D SDF for HMDB0061879 ((S)-Methylbutanethioic acid)


  Mrv1652310012003002D          

  7  6  0  0  0  0            999 V2000
10004.439210004.2128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.723910004.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.154410004.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.439210003.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.723910005.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.008710004.2128    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10005.868610004.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061879

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](C)C(S)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10OS/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1

> <INCHI_KEY>
QJDRJTFSPVQEDV-BYPYZUCNSA-N

> <FORMULA>
C5H10OS

> <MOLECULAR_WEIGHT>
118.19

> <EXACT_MASS>
118.045236116

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.993606875093992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-methylbutanethioic S-acid

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
1.978259429

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5856906334564309

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
32.8599

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-methylbutanethioic S-acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061879 ((S)-Methylbutanethioic acid)

HMDB0061879
     RDKit          3D
(S)-Methylbutanethioic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.8529   -0.1979    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -0.3193   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    0.1808   -0.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5594    1.6410    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -0.6476    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -0.1695    2.0304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3792    0.6821 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9414    0.7763    0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.9935    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665   -0.3264   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    0.2592   -1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -1.3653   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.0958   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0413    2.1970   -0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    1.7751    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136    1.9911    0.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -2.5176   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  6
  4 14  1  0
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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PDB for HMDB0061879 ((S)-Methylbutanethioic acid)

HEADER    PROTEIN                                 01-OCT-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-20         0                                  
HETATM    1  C   UNK     0    8674.9538674.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8673.6188675.299   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8676.2888675.299   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.9538672.991   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8673.6188676.838   0.000  0.00  0.00           O+0
HETATM    6  S   UNK     0    8672.2838674.531   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0    8677.6218674.531   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0061879 ((S)-Methylbutanethioic acid)

COMPND    HMDB0061879
HETATM    1  C1  UNL     1       1.853  -0.198   0.053  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.664  -0.319  -0.838  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.607   0.181  -0.232  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.559   1.641   0.150  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.080  -0.648   0.910  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.218  -0.170   2.030  1.00  0.00           O  
HETATM    7  S1  UNL     1      -1.466  -2.379   0.682  1.00  0.00           S  
HETATM    8  H1  UNL     1       1.941   0.776   0.556  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.925  -0.994   0.815  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.766  -0.326  -0.596  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.847   0.259  -1.764  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.531  -1.365  -1.118  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.399   0.096  -1.027  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.041   2.197  -0.646  1.00  0.00           H  
HETATM   15  H8  UNL     1      -0.113   1.775   1.155  1.00  0.00           H  
HETATM   16  H9  UNL     1      -1.614   1.991   0.202  1.00  0.00           H  
HETATM   17  H10 UNL     1      -2.431  -2.518  -0.331  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    5   13
CONECT    4   14   15   16
CONECT    5    6    6    7
CONECT    7   17
END
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SMILES for HMDB0061879 ((S)-Methylbutanethioic acid)

CC[C@H](C)C(S)=O
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INCHI for HMDB0061879 ((S)-Methylbutanethioic acid)

InChI=1S/C5H10OS/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-Methylbutanethioic acidHMDB
(S)-Methylbutanethioic acidHMDB
2-Methylbutanethioic acidHMDB
Methylbutanethioic acidHMDB
Chemical FormulaC5H10OS
Average Molecular Weight118.19
Monoisotopic Molecular Weight118.045236116
IUPAC Name(2S)-2-methylbutanethioic S-acid
Traditional Name(2S)-2-methylbutanethioic S-acid
CAS Registry Number929103-96-8
SMILES
CC[C@H](C)C(S)=O
InChI Identifier
InChI=1S/C5H10OS/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1
InChI KeyQJDRJTFSPVQEDV-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carbothioic s-acids. These are organic acids with the general formula RCS-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarbothioic S-acids
Sub ClassNot Available
Direct ParentCarbothioic S-acids
Alternative Parents
Substituents
  • Carbothioic s-acid
  • Carbodithioic acid
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility184 g/LALOGPS
logP2.51ALOGPS
logP1.98ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.86 m³·mol⁻¹ChemAxon
Polarizability12.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+128.85230932474
DeepCCS[M-H]-126.63630932474
DeepCCS[M-2H]-162.75430932474
DeepCCS[M+Na]+137.44330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-Methylbutanethioic acidCC[C@H](C)C(S)=O1488.0Standard polar33892256
(S)-Methylbutanethioic acidCC[C@H](C)C(S)=O972.1Standard non polar33892256
(S)-Methylbutanethioic acidCC[C@H](C)C(S)=O943.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Methylbutanethioic acid,1TMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C1096.4Semi standard non polar33892256
(S)-Methylbutanethioic acid,1TMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C1095.6Standard non polar33892256
(S)-Methylbutanethioic acid,1TMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C1220.3Standard polar33892256
(S)-Methylbutanethioic acid,1TBDMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C(C)(C)C1331.3Semi standard non polar33892256
(S)-Methylbutanethioic acid,1TBDMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C(C)(C)C1340.8Standard non polar33892256
(S)-Methylbutanethioic acid,1TBDMS,isomer #1CC[C@H](C)C(=O)S[Si](C)(C)C(C)(C)C1372.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Methylbutanethioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Methylbutanethioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 10V, Positive-QTOFsplash10-014r-8900000000-e328e7cf22cbe1c162372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 20V, Positive-QTOFsplash10-0a4i-9100000000-780666774724ab9286742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 40V, Positive-QTOFsplash10-06r6-9000000000-6830d0bbd3b6874919112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 10V, Negative-QTOFsplash10-014i-0900000000-4bd8fda8e68e209a86e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 20V, Negative-QTOFsplash10-0159-6900000000-f1b863ba0ff8a8bf37cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Methylbutanethioic acid 40V, Negative-QTOFsplash10-0bu0-9100000000-54f4b67b7190c902331d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87203143
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.