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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:08 UTC
Update Date2022-03-07 02:52:30 UTC
HMDB IDHMDB0030327
Secondary Accession Numbers
  • HMDB30327
Metabolite Identification
Common NamePerlolyrine
DescriptionPerlolyrine, also known as substance ys, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Perlolyrine has been detected, but not quantified in, a few different foods, such as herbs and spices, saffrons (Crocus sativus), and soy beans (Glycine max). This could make perlolyrine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Perlolyrine.
Structure
Data?1563861969
Synonyms
ValueSource
Substance ysMeSH
Yellow substance ysMeSH
2-(b-Carbolin-1-yl)-5-hydroxymethylfuranHMDB
2-DehydrocarbonylflazinHMDB
5-(9H-pyrido(3,4-b)indol-1-yl)-2-FuranmethanolHMDB
5-(9H-pyrido[3,4-b]indol-1-yl)-2-Furanmethanol, 9ciHMDB
Alkaloid ysHMDB
[5-(9H-beta-Carbolin-1-yl)-2-furyl]methanolHMDB
Chemical FormulaC16H12N2O2
Average Molecular Weight264.2787
Monoisotopic Molecular Weight264.089877638
IUPAC Name(5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol
Traditional Nameperlolyrine
CAS Registry Number29700-20-7
SMILES
OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21
InChI Identifier
InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2
InChI KeyKFUCYPGCMLPUMT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Indole
  • Indole or derivatives
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Furan
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.089 g/LALOGPS
logP2.66ALOGPS
logP2.12ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.43ChemAxon
pKa (Strongest Basic)2.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.05 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.16 m³·mol⁻¹ChemAxon
Polarizability28.59 ųChemAxon
Number of Rings4ChemAxon
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]+160.73631661259
DarkChem[M-H]-163.7331661259
DeepCCS[M-2H]-190.7330932474
DeepCCS[M+Na]+166.27430932474
AllCCS[M+H]+162.232859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+166.032859911
AllCCS[M+Na]+167.032859911
AllCCS[M-H]-165.532859911
AllCCS[M+Na-2H]-164.632859911
AllCCS[M+HCOO]-163.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PerlolyrineOCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C213693.8Standard polar33892256
PerlolyrineOCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C212687.8Standard non polar33892256
PerlolyrineOCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C212947.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Perlolyrine,1TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O12864.2Semi standard non polar33892256
Perlolyrine,1TMS,isomer #2C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C212844.0Semi standard non polar33892256
Perlolyrine,2TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O12844.7Semi standard non polar33892256
Perlolyrine,2TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O12744.8Standard non polar33892256
Perlolyrine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O13096.4Semi standard non polar33892256
Perlolyrine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C213039.4Semi standard non polar33892256
Perlolyrine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O13248.2Semi standard non polar33892256
Perlolyrine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O13146.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Perlolyrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-0190000000-366a1478638155f0b62d2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perlolyrine GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9263000000-7f547b2cb0cea39ddfb42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perlolyrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perlolyrine 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 - Perlolyrine 10V, Positive-QTOFsplash10-014i-0090000000-5aae234b5117054b9b0e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOFsplash10-014j-0090000000-c544b87c4bab088505c92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOFsplash10-014i-4960000000-89238e7378563fe9e3332015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOFsplash10-03di-0090000000-4022863ec611eb08878d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOFsplash10-01qa-0190000000-05b5aa6ed9c4bfaf6e902015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOFsplash10-0gb9-3490000000-2bf143ea0acfda8a07a22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOFsplash10-03e9-0090000000-5db7fd9219b8a82d732a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOFsplash10-03di-0090000000-3ba2386f41e0df1e8c342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOFsplash10-0006-2920000000-e2eeb6b2f419c48d29aa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 10V, Positive-QTOFsplash10-014i-0090000000-e6e22b9224f216c1ee622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOFsplash10-014i-0290000000-021deff5c273a5c42dc82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOFsplash10-05n0-0490000000-5349405c626001a3e4732021-09-25Wishart 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 IDFDB002170
KNApSAcK IDC00001756
Chemspider ID140791
KEGG Compound IDC09231
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160179
PDB IDNot Available
ChEBI ID610215
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.. .