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Record Information
Version1.0
Created at2022-03-17 19:44:50 UTC
Updated at2022-03-17 19:44:50 UTC
NP-MRD IDNP0045884
Secondary Accession NumbersNone
Natural Product Identification
Common NamePerlolyrine
DescriptionPerlolyrine, also known as alkaloid 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 is a moderately basic compound (based on its pKa). Outside of the human body, Perlolyrine has been detected, but not quantified in, a few different foods, such as herbs and spices, saffrons, and soy beans. Perlolyrine is found in Apis cerana, Codonopsis pilosula , Codonopsis tangshen , Codonopsis pilosula var.modesta , Houttuynia cordata , Ligusticum chuanxiong, Lolium chuanxiong, Lolium perenne , Lycium chinense, Ophiocordyceps sinensis, Panax ginseng , Polygala tenuifolia , Streptomyces spp. and Tribulus terrestris . This could make perlolyrine a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
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
Substance ysMeSH
Yellow substance ysMeSH
Chemical FormulaC16H12N2O2
Average Mass264.2787 Da
Monoisotopic Mass264.08988 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Codonopsis pilosulaPlant
Codonopsis pilosula subsp. tangshenPlant
Codonopsis pilosula var.modestaPlant
Crocus sativusFooDB
Glycine maxFooDB
Houttuynia cordataPlant
Ligusticum chuanxiongLOTUS Database
Lolium chuanxiongPlant
Lolium perennePlant
Lycium chinenseLOTUS Database
Ophiocordyceps sinensisLOTUS Database
Panax ginsengPlant
Polygala tenuifoliaPlant
Streptomyces spp.Bacteria
Tribulus terrestrisPlant
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0030327
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General ReferencesNot Available