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Showing metabocard for 1-(Methylthio)-propane (HMDB0061871)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:18 UTC
Update Date2023-02-21 17:30:29 UTC
HMDB IDHMDB0061871
Secondary Accession Numbers
  • HMDB61871
Metabolite Identification
Common Name1-(Methylthio)-propane
Description1-(Methylthio)-propane belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups. 1-(Methylthio)-propane is possibly neutral. 1-(Methylthio)-propane is an alliaceous, creamy, and green tasting compound. Outside of the human body, 1-(Methylthio)-propane is found, on average, in the highest concentration within kohlrabis. 1-(Methylthio)-propane has also been detected, but not quantified in, garden onions. This could make 1-(methylthio)-propane a potential biomarker for the consumption of these foods.
Structure
Data?1677000629
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061871 (1-(Methylthio)-propane)


  Mrv0541 02241217482D          

  5  4  0  0  0  0            999 V2000
    1.0731   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0731    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    0.2064    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.6186    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0061871 (1-(Methylthio)-propane)

HMDB0061871
     RDKit          3D
1-(Methylthio)-propane
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.1845    0.4649   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -0.5756    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -0.6597   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696    0.8686   -0.2672 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147    0.4932   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307    0.0536   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    0.6844    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6578    1.4084   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337   -0.3144    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -1.5450    0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184   -0.7442   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284   -1.5036   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    1.2041    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    0.7019   -0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9028   -0.5368    0.3274 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
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
M  END
Download

3D SDF for HMDB0061871 (1-(Methylthio)-propane)


  Mrv0541 02241217482D          

  5  4  0  0  0  0            999 V2000
    1.0731   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0731    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    0.2064    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.6186    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061871

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCSC

> <INCHI_IDENTIFIER>
InChI=1S/C4H10S/c1-3-4-5-2/h3-4H2,1-2H3

> <INCHI_KEY>
ZOASGOXWEHUTKZ-UHFFFAOYSA-N

> <FORMULA>
C4H10S

> <MOLECULAR_WEIGHT>
90.187

> <EXACT_MASS>
90.05032101

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
11.279269092313896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(methylsulfanyl)propane

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.999131887

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
28.2135

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-propylmethylsulfide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061871 (1-(Methylthio)-propane)

HMDB0061871
     RDKit          3D
1-(Methylthio)-propane
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.1845    0.4649   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -0.5756    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -0.6597   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696    0.8686   -0.2672 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147    0.4932   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307    0.0536   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124    0.6844    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6578    1.4084   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337   -0.3144    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -1.5450    0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184   -0.7442   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284   -1.5036   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    1.2041    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    0.7019   -0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9028   -0.5368    0.3274 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
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  5 14  1  0
  5 15  1  0
M  END
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PDB for HMDB0061871 (1-(Methylthio)-propane)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.003  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.003   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.155   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -0.616   0.385   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      -2.003   1.155   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0061871 (1-(Methylthio)-propane)

COMPND    HMDB0061871
HETATM    1  C1  UNL     1      -2.185   0.465  -0.374  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.233  -0.576   0.174  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.046  -0.660  -0.635  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.970   0.869  -0.267  1.00  0.00           S  
HETATM    5  C4  UNL     1       2.715   0.493  -0.018  1.00  0.00           C  
HETATM    6  H1  UNL     1      -2.731   0.054  -1.251  1.00  0.00           H  
HETATM    7  H2  UNL     1      -2.912   0.684   0.448  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.658   1.408  -0.653  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.934  -0.314   1.208  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.739  -1.545   0.095  1.00  0.00           H  
HETATM   11  H6  UNL     1      -0.218  -0.744  -1.697  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.628  -1.504  -0.235  1.00  0.00           H  
HETATM   13  H8  UNL     1       3.108   1.204   0.748  1.00  0.00           H  
HETATM   14  H9  UNL     1       3.240   0.702  -0.984  1.00  0.00           H  
HETATM   15  H10 UNL     1       2.903  -0.537   0.327  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5
CONECT    5   13   14   15
END
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SMILES for HMDB0061871 (1-(Methylthio)-propane)

CCCSC
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INCHI for HMDB0061871 (1-(Methylthio)-propane)

InChI=1S/C4H10S/c1-3-4-5-2/h3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC4H10S
Average Molecular Weight90.187
Monoisotopic Molecular Weight90.05032101
IUPAC Name1-(methylsulfanyl)propane
Traditional NameN-propylmethylsulfide
CAS Registry NumberNot Available
SMILES
CCCSC
InChI Identifier
InChI=1S/C4H10S/c1-3-4-5-2/h3-4H2,1-2H3
InChI KeyZOASGOXWEHUTKZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassDialkylthioethers
Direct ParentDialkylthioethers
Alternative Parents
Substituents
  • Dialkylthioether
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
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 Solubility1.81 g/LALOGPS
logP1.96ALOGPS
logP2ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.21 m³·mol⁻¹ChemAxon
Polarizability11.28 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
DarkChem[M+H]+116.85931661259
DarkChem[M-H]-112.11131661259
DeepCCS[M+H]+126.02430932474
DeepCCS[M-H]-124.11630932474
DeepCCS[M-2H]-159.55430932474
DeepCCS[M+Na]+133.60530932474
AllCCS[M+H]+121.132859911
AllCCS[M+H-H2O]+116.732859911
AllCCS[M+NH4]+125.132859911
AllCCS[M+Na]+126.332859911
AllCCS[M-H]-145.032859911
AllCCS[M+Na-2H]-150.532859911
AllCCS[M+HCOO]-156.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-(Methylthio)-propaneCCCSC931.3Standard polar33892256
1-(Methylthio)-propaneCCCSC677.8Standard non polar33892256
1-(Methylthio)-propaneCCCSC713.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-(Methylthio)-propane GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r7-9000000000-d4a5340b139252c00a552017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(Methylthio)-propane 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 - 1-(Methylthio)-propane 10V, Positive-QTOFsplash10-0006-9000000000-dd37e24185a3dcff488b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 20V, Positive-QTOFsplash10-0006-9000000000-19939fa04634eb6bb2042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 40V, Positive-QTOFsplash10-0006-9000000000-b9d1481e466d2df04d0e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 10V, Negative-QTOFsplash10-000j-9000000000-e90fe11d56312886b9302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 20V, Negative-QTOFsplash10-0002-9000000000-b26f3bc56f31a18bb4fc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 40V, Negative-QTOFsplash10-0002-9000000000-3a2da9a2a9fe1631013c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 10V, Positive-QTOFsplash10-0006-9000000000-1e46987b746c0a0b151d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 20V, Positive-QTOFsplash10-03di-9000000000-7a0e20319c077245f0ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 40V, Positive-QTOFsplash10-0002-9000000000-3330e0850c49d723a7052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 10V, Negative-QTOFsplash10-000i-9000000000-c15245c3ae5818f2f7132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 20V, Negative-QTOFsplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Methylthio)-propane 40V, Negative-QTOFsplash10-0002-9000000000-38488f22b37c4e5a76f72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C 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+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020354
KNApSAcK IDNot Available
Chemspider ID18607
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19754
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Awaleh MO, Baril-Robert F, Reber C, Badia A, Brosse F: Gold(I)-dithioether supramolecular polymers: synthesis, characterization, and luminescence. Inorg Chem. 2008 Apr 21;47(8):2964-74. doi: 10.1021/ic701275k. [PubMed:18366159 ]
  2. Sangster SA, Caldwell J, Smith RL, Farmer PB: Metabolism of anethole. I. Pathways of metabolism in the rat and mouse. Food Chem Toxicol. 1984 Sep;22(9):695-706. [PubMed:6541622 ]
  3. Bergamini P, Bertolasi V, Marvelli L, Canella A, Gavioli R, Mantovani N, Manas S, Romerosa A: Phosphinic platinum complexes with 8-thiotheophylline derivatives: synthesis, characterization, and antiproliferative activity. Inorg Chem. 2007 May 14;46(10):4267-76. Epub 2007 Apr 20. [PubMed:17444631 ]
  4. Trabue S, Scoggin K, Tjandrakusuma S, Rasmussen MA, Reilly PJ: Ruminal fermentation of propylene glycol and glycerol. J Agric Food Chem. 2007 Aug 22;55(17):7043-51. Epub 2007 Jul 27. [PubMed:17655323 ]
  5. Gonda I, Bar E, Portnoy V, Lev S, Burger J, Schaffer AA, Tadmor Y, Gepstein S, Giovannoni JJ, Katzir N, Lewinsohn E: Branched-chain and aromatic amino acid catabolism into aroma volatiles in Cucumis melo L. fruit. J Exp Bot. 2010 Feb;61(4):1111-23. doi: 10.1093/jxb/erp390. Epub 2010 Jan 11. [PubMed:20065117 ]
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