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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:23:15 UTC
Update Date2022-03-07 02:53:48 UTC
HMDB IDHMDB0033637
Secondary Accession Numbers
  • HMDB33637
Metabolite Identification
Common NameFistulosin
DescriptionFistulosin belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Fistulosin has been detected, but not quantified in, several different foods, such as red onion, garden onion (var.), welsh onions (Allium fistulosum), green onion, and onion-family vegetables. This could make fistulosin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Fistulosin.
Structure
Data?1563862436
Synonyms
ValueSource
1,2-dihydro-2-Octadecyl-3H-indol-3-oneHMDB
2-Octadecyl-1H-indol-3-olHMDB
FistulosinMeSH
Chemical FormulaC26H43NO
Average Molecular Weight385.6257
Monoisotopic Molecular Weight385.334465003
IUPAC Name2-octadecyl-1H-indol-3-ol
Traditional Name2-octadecyl-1H-indol-3-ol
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N1
InChI Identifier
InChI=1S/C26H43NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22-25-26(28)23-20-18-19-21-24(23)27-25/h18-21,27-28H,2-17,22H2,1H3
InChI KeyAYPYUZXAFNVUEC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point80 - 83 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.2e-05 g/LALOGPS
logP9.48ALOGPS
logP9.6ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity122.42 m³·mol⁻¹ChemAxon
Polarizability52.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+200.57530932474
DeepCCS[M-H]-198.02430932474
DeepCCS[M-2H]-231.22830932474
DeepCCS[M+Na]+206.91930932474
AllCCS[M+H]+210.932859911
AllCCS[M+H-H2O]+208.532859911
AllCCS[M+NH4]+213.132859911
AllCCS[M+Na]+213.832859911
AllCCS[M-H]-208.532859911
AllCCS[M+Na-2H]-211.132859911
AllCCS[M+HCOO]-214.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FistulosinCCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N13815.8Standard polar33892256
FistulosinCCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N13100.4Standard non polar33892256
FistulosinCCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N13331.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fistulosin,1TMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C)C2=CC=CC=C2[NH]13228.4Semi standard non polar33892256
Fistulosin,1TMS,isomer #2CCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N1[Si](C)(C)C3406.7Semi standard non polar33892256
Fistulosin,2TMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C3372.5Semi standard non polar33892256
Fistulosin,2TMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C3144.1Standard non polar33892256
Fistulosin,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2[NH]13441.3Semi standard non polar33892256
Fistulosin,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCC1=C(O)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3583.6Semi standard non polar33892256
Fistulosin,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3716.2Semi standard non polar33892256
Fistulosin,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCC1=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3403.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fistulosin GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r5-5962000000-80e0b0bcaba27a53158f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fistulosin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9663400000-c728c5c6f4aaea2ea8cd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fistulosin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fistulosin 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 - Fistulosin 10V, Positive-QTOFsplash10-000i-0019000000-12ab4291449e7ad30dfe2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 20V, Positive-QTOFsplash10-000i-4898000000-a42c3d33b514ea78d5412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 40V, Positive-QTOFsplash10-052o-9852000000-44106a70abca0c41b12b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 10V, Negative-QTOFsplash10-001i-0009000000-0a0a4c6773c5b32cee6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 20V, Negative-QTOFsplash10-001i-0209000000-9ecfca521f691ef007922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 40V, Negative-QTOFsplash10-001i-4901000000-acdfe0a2120c965568ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 10V, Negative-QTOFsplash10-001i-0009000000-3a23c683a43a5b72c4bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 20V, Negative-QTOFsplash10-001i-0209000000-b62a6447d3107af24fc52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 40V, Negative-QTOFsplash10-001l-2925000000-57a304b5e126024f59962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 10V, Positive-QTOFsplash10-000i-0009000000-fdfd5e67aa5d60f2641f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 20V, Positive-QTOFsplash10-0019-4629000000-d31727eed46ccd27f90d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fistulosin 40V, Positive-QTOFsplash10-055f-9301000000-d71945cdec06c28622ab2021-09-25Wishart 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 IDFDB011736
KNApSAcK IDNot Available
Chemspider ID9749331
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11574561
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.. .