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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:40:35 UTC
Update Date2021-09-14 14:58:45 UTC
HMDB IDHMDB0033901
Secondary Accession Numbers
  • HMDB33901
Metabolite Identification
Common NameGlyceollin I
DescriptionIsopentyl mercaptan, also known as 2-methyl-4-butanethiol or fema 3858, belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. Isopentyl mercaptan is an extremely weak basic (essentially neutral) compound (based on its pKa). Isopentyl mercaptan is a glue and onion tasting compound. Outside of the human body, Isopentyl mercaptan has been detected, but not quantified in, alcoholic beverages. This could make isopentyl mercaptan a potential biomarker for the consumption of these foods.
Structure
Data?1563862478
Synonyms
ValueSource
1-Mercapto-3-methylbutaneHMDB
2-Methyl-4-butanethiolHMDB
3-Methyl-1-butanethiolHMDB
3-Methyl-1-butylthiolHMDB
3-Methylbutane-1-thiolHMDB
3-MethylbutanethiolHMDB
FEMA 3858HMDB
Isoamyl mercaptanHMDB
Isoamyl sulfhydrateHMDB
Isoamyl thioalcoholHMDB
IsoamylthiolHMDB
IsopentanethiolHMDB
Thioisoamyl alcoholHMDB
rac-Glyceollin IChEMBL, HMDB
(-) - Glyceollin IHMDB
(-)-Glyceollin IHMDB
2,2-Dimethyl-2H,6H-benzofuro[3,2-c]pyrano[2,3-H][1]benzopyran-6a,9(11ah)-diol, 9ciHMDB
GlyceollinHMDB
Glyceollin IMeSH
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Name17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
Traditional Name17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
CAS Registry Number57103-57-8
SMILES
CC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2(O)CO1
InChI Identifier
InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3
InChI KeyYIFYYPKWOQSCRI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

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 Solubility0.06 g/LALOGPS
logP10(3.24) g/LALOGPS
logP10(2.91) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.08 m³·mol⁻¹ChemAxon
Polarizability35.63 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.73331661259
DarkChem[M-H]-178.52131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glyceollin ICC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2(O)CO14085.0Standard polar33892256
Glyceollin ICC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2(O)CO12793.5Standard non polar33892256
Glyceollin ICC1(C)OC2=C(C=C1)C1=C(C=C2)C2OC3=C(C=CC(O)=C3)C2(O)CO13053.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glyceollin I,1TMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC2(O)C4=CC=C(O[Si](C)(C)C)C=C4OC32)O12887.0Semi standard non polar33892256
Glyceollin I,1TMS,isomer #2CC1(C)C=CC2=C(C=CC3=C2OCC2(O[Si](C)(C)C)C4=CC=C(O)C=C4OC32)O12831.5Semi standard non polar33892256
Glyceollin I,2TMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC2(O[Si](C)(C)C)C4=CC=C(O[Si](C)(C)C)C=C4OC32)O12868.1Semi standard non polar33892256
Glyceollin I,1TBDMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC2(O)C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OC32)O13147.7Semi standard non polar33892256
Glyceollin I,1TBDMS,isomer #2CC1(C)C=CC2=C(C=CC3=C2OCC2(O[Si](C)(C)C(C)(C)C)C4=CC=C(O)C=C4OC32)O13089.1Semi standard non polar33892256
Glyceollin I,2TBDMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC2(O[Si](C)(C)C(C)(C)C)C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OC32)O13356.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin I GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1729000000-509c3c88ec1754df6c4a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin I GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9504700000-aaaddd9634462f5876d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin I 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 - Glyceollin I 10V, Positive-QTOFsplash10-000i-1009000000-7da7b6353a3bf7f2ada42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Positive-QTOFsplash10-000i-2049000000-855330d2cec507834ce02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Positive-QTOFsplash10-00kg-9110000000-8a0d1442e4b4f3322f0f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 10V, Positive-QTOFsplash10-000i-1009000000-7da7b6353a3bf7f2ada42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Positive-QTOFsplash10-000i-2049000000-855330d2cec507834ce02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Positive-QTOFsplash10-00kg-9110000000-8a0d1442e4b4f3322f0f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 10V, Negative-QTOFsplash10-000i-0009000000-37c5e7045763865109d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Negative-QTOFsplash10-000i-0019000000-4f535f09f63f7d0c10302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Negative-QTOFsplash10-0udi-1091000000-7a0481b012fd7d6d95ca2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 10V, Negative-QTOFsplash10-000i-0009000000-37c5e7045763865109d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Negative-QTOFsplash10-000i-0019000000-4f535f09f63f7d0c10302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Negative-QTOFsplash10-0udi-1091000000-7a0481b012fd7d6d95ca2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 10V, Negative-QTOFsplash10-000i-0009000000-fba49930c01349472a4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Negative-QTOFsplash10-000j-0079000000-6471d5b92e9794bce9522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Negative-QTOFsplash10-0007-5093000000-9b8151ac497c3e7f01682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 10V, Positive-QTOFsplash10-000i-0009000000-2b8ef97f349df851f3ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 20V, Positive-QTOFsplash10-000i-0019000000-9abe671c9118c63fb6942021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin I 40V, Positive-QTOFsplash10-000i-0479000000-87f665e2b92e3c4fe6312021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB012097
KNApSAcK IDNot Available
Chemspider ID10462
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10925
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .