Hmdb loader

Showing metabocard for Lenthionine (HMDB0031258)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:57 UTC
Update Date2023-02-21 17:20:13 UTC
HMDB IDHMDB0031258
Secondary Accession Numbers
  • HMDB31258
Metabolite Identification
Common NameLenthionine
DescriptionLenthionine belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl). Lenthionine is a mushroom tasting compound. Lenthionine has been detected, but not quantified in, several different foods, such as common mushrooms (Agaricus bisporus), green vegetables, mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make lenthionine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Lenthionine.
Structure
Data?1677000013
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031258 (Lenthionine)


  Mrv0541 05061305502D          

  7  7  0  0  0  0            999 V2000
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031258 (Lenthionine)

HMDB0031258
     RDKit          3D
Lenthionine
 11 11  0  0  0  0  0  0  0  0999 V2000
   -1.9049   -0.4645   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057   -1.4646   -0.9319 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.3365   -1.2662 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -0.1037    0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    1.0979    1.2796 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    2.2834    0.0253 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8434    1.2590   -0.6934 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -0.8792   -0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -0.5633    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -1.0653    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.2369    0.1159 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
  5  6  1  0
  6  7  1  0
  7  1  1  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  4 11  1  0
M  END
Download

3D SDF for HMDB0031258 (Lenthionine)


  Mrv0541 05061305502D          

  7  7  0  0  0  0            999 V2000
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031258

> <DATABASE_NAME>
hmdb

> <SMILES>
C1SSCSSS1

> <INCHI_IDENTIFIER>
InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2

> <INCHI_KEY>
DZKOKXZNCDGVRY-UHFFFAOYSA-N

> <FORMULA>
C2H4S5

> <MOLECULAR_WEIGHT>
188.378

> <EXACT_MASS>
187.891653578

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
16.70302525893579

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,5,6-pentathiepane

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
2.2012452136666667

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
46.1032

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lenthionine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0031258 (Lenthionine)

HMDB0031258
     RDKit          3D
Lenthionine
 11 11  0  0  0  0  0  0  0  0999 V2000
   -1.9049   -0.4645   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057   -1.4646   -0.9319 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.3365   -1.2662 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -0.1037    0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    1.0979    1.2796 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553    2.2834    0.0253 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8434    1.2590   -0.6934 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -0.8792   -0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -0.5633    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -1.0653    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.2369    0.1159 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
  5  6  1  0
  6  7  1  0
  7  1  1  0
  1  8  1  0
  1  9  1  0
  4 10  1  0
  4 11  1  0
M  END
Download

PDB for HMDB0031258 (Lenthionine)

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       2.986   1.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       1.599   2.545   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       0.211   1.877   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0       3.329   0.375   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0       0.829  -0.829   0.000  0.00  0.00           S+0
HETATM    7  S   UNK     0       2.369  -0.829   0.000  0.00  0.00           S+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    4                                                       
CONECT    4    2    3                                                       
CONECT    5    1    7                                                       
CONECT    6    2    7                                                       
CONECT    7    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
Download

3D PDB for HMDB0031258 (Lenthionine)

COMPND    HMDB0031258
HETATM    1  C1  UNL     1      -1.905  -0.464  -0.136  1.00  0.00           C  
HETATM    2  S1  UNL     1      -0.606  -1.465  -0.932  1.00  0.00           S  
HETATM    3  S2  UNL     1       1.150  -0.337  -1.266  1.00  0.00           S  
HETATM    4  C2  UNL     1       2.023  -0.104   0.315  1.00  0.00           C  
HETATM    5  S3  UNL     1       1.063   1.098   1.280  1.00  0.00           S  
HETATM    6  S4  UNL     1      -0.155   2.283   0.025  1.00  0.00           S  
HETATM    7  S5  UNL     1      -1.843   1.259  -0.693  1.00  0.00           S  
HETATM    8  H1  UNL     1      -2.876  -0.879  -0.513  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.890  -0.563   0.961  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.986  -1.065   0.844  1.00  0.00           H  
HETATM   11  H4  UNL     1       3.053   0.237   0.116  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3
CONECT    3    4
CONECT    4    5   10   11
CONECT    5    6
CONECT    6    7
END
Download

SMILES for HMDB0031258 (Lenthionine)

C1SSCSSS1
Download

INCHI for HMDB0031258 (Lenthionine)

InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
LenthioninChEBI
1,2,3,5,6-PentathiepaneKegg
1,2,3,5,6-PentathiacycloheptaneHMDB
Chemical FormulaC2H4S5
Average Molecular Weight188.378
Monoisotopic Molecular Weight187.891653578
IUPAC Name1,2,3,5,6-pentathiepane
Traditional Namelenthionine
CAS Registry Number292-46-6
SMILES
C1SSCSSS1
InChI Identifier
InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2
InChI KeyDZKOKXZNCDGVRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassOrganic trisulfides
Sub ClassNot Available
Direct ParentOrganic trisulfides
Alternative Parents
Substituents
  • Organic trisulfide
  • Organic disulfide
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point60 - 61 °CNot Available
Boiling Point287.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility532.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.238 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
logP0.96ALOGPS
logP2.2ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.1 m³·mol⁻¹ChemAxon
Polarizability16.7 ųChemAxon
Number of Rings1ChemAxon
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]+135.33631661259
DarkChem[M-H]-128.25531661259
DeepCCS[M+H]+133.72830932474
DeepCCS[M-H]-131.76430932474
DeepCCS[M-2H]-167.30830932474
DeepCCS[M+Na]+141.67530932474
AllCCS[M+H]+131.132859911
AllCCS[M+H-H2O]+126.932859911
AllCCS[M+NH4]+135.132859911
AllCCS[M+Na]+136.232859911
AllCCS[M-H]-126.532859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-132.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.01 minutes32390414
Predicted by Siyang on May 30, 202212.8304 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.19 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid214.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1880.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid713.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid278.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid525.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid314.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid647.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid759.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)717.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1312.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid500.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1454.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid521.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid494.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate833.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA632.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water240.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LenthionineC1SSCSSS12684.6Standard polar33892256
LenthionineC1SSCSSS11611.3Standard non polar33892256
LenthionineC1SSCSSS11577.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lenthionine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a74-8900000000-aa070964843c2b308b162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lenthionine 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 - Lenthionine 10V, Positive-QTOFsplash10-000i-0900000000-76a68cfd48f4003290192016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 20V, Positive-QTOFsplash10-000i-1900000000-af9c6aba1fc9402d12172016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 40V, Positive-QTOFsplash10-004i-9400000000-c9514b0cb1a376039f5c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 10V, Negative-QTOFsplash10-000l-2900000000-72be2c357818b8ae15b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 20V, Negative-QTOFsplash10-00fu-9500000000-192eb03ed8363aec4eec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 40V, Negative-QTOFsplash10-002f-9500000000-35101930bb8ef33fe3a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 10V, Negative-QTOFsplash10-002r-4900000000-95cd86942d00d4909a1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 20V, Negative-QTOFsplash10-004i-9000000000-19ebb4d56cc8db97f7fe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 40V, Negative-QTOFsplash10-004i-9100000000-096fa5ecaa1ad3ec90262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 10V, Positive-QTOFsplash10-000i-0900000000-c55b25ea741d2fc407a72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 20V, Positive-QTOFsplash10-000i-3900000000-27fda75c6c3ebd5b488c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lenthionine 40V, Positive-QTOFsplash10-004u-9200000000-3f71520038724896348a2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB003295
KNApSAcK IDC00001256
Chemspider ID60844
KEGG Compound IDC08382
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLenthionine
METLIN IDNot Available
PubChem Compound67521
PDB IDNot Available
ChEBI ID6408
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1576921
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .