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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:11:34 UTC
Update Date2022-03-07 02:53:43 UTC
HMDB IDHMDB0033459
Secondary Accession Numbers
  • HMDB33459
Metabolite Identification
Common NameFlazine
DescriptionFlazine 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. Flazine has been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and soy beans (Glycine max). This could make flazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Flazine.
Structure
Data?1563862409
Synonyms
ValueSource
1-[5-(Hydroxymethyl)-2-furanyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid, 9ciHMDB
FlazinHMDB
1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylateGenerator
FlazineMeSH
Chemical FormulaC17H12N2O4
Average Molecular Weight308.2882
Monoisotopic Molecular Weight308.079706882
IUPAC Name1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry Number100041-05-2
SMILES
OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O
InChI Identifier
InChI=1S/C17H12N2O4/c20-8-9-5-6-14(23-9)16-15-11(7-13(19-16)17(21)22)10-3-1-2-4-12(10)18-15/h1-7,18,20H,8H2,(H,21,22)
InChI KeyUSBWYUYKHHILLZ-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
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Furan
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point231 - 233 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.26 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.64ALOGPS
logP2.16ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)0.28ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.35 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.05 m³·mol⁻¹ChemAxon
Polarizability32.09 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]+172.98231661259
DarkChem[M-H]-172.46431661259
DeepCCS[M+H]+170.00930932474
DeepCCS[M-H]-167.65130932474
DeepCCS[M-2H]-200.91330932474
DeepCCS[M+Na]+176.1430932474
AllCCS[M+H]+172.132859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+175.532859911
AllCCS[M+Na]+176.432859911
AllCCS[M-H]-173.332859911
AllCCS[M+Na-2H]-172.432859911
AllCCS[M+HCOO]-171.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlazineOCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O4039.2Standard polar33892256
FlazineOCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O3005.9Standard non polar33892256
FlazineOCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O3348.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Flazine,1TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2[NH]C2=CC=CC=C23)O13292.6Semi standard non polar33892256
Flazine,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=C(CO)O2)=N13282.6Semi standard non polar33892256
Flazine,1TMS,isomer #3C[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=C(CO)O3)=C213267.1Semi standard non polar33892256
Flazine,2TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O13304.3Semi standard non polar33892256
Flazine,2TMS,isomer #2C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O13239.6Semi standard non polar33892256
Flazine,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=C(CO)O3)=N1)N([Si](C)(C)C)C1=CC=CC=C213250.7Semi standard non polar33892256
Flazine,3TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O13248.8Semi standard non polar33892256
Flazine,3TMS,isomer #1C[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C)=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O13160.3Standard non polar33892256
Flazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2[NH]C2=CC=CC=C23)O13516.5Semi standard non polar33892256
Flazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=C(CO)O2)=N13503.4Semi standard non polar33892256
Flazine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=C(CO)O3)=C213514.2Semi standard non polar33892256
Flazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2[NH]C2=CC=CC=C23)O13709.2Semi standard non polar33892256
Flazine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O13680.6Semi standard non polar33892256
Flazine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=C(CO)O3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C213655.6Semi standard non polar33892256
Flazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O13790.3Semi standard non polar33892256
Flazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC(C(=O)O[Si](C)(C)C(C)(C)C)=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O13656.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p6-0090000000-0deb89f70a9d791791462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flazine GC-MS (2 TMS) - 70eV, Positivesplash10-01w0-7009300000-ecca7acccf29e0231cd12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flazine 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 - Flazine 10V, Positive-QTOFsplash10-0a4l-0095000000-1263d337948d7d371f362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 20V, Positive-QTOFsplash10-03dl-0191000000-598b7ee60742ff605b5e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 40V, Positive-QTOFsplash10-014i-1190000000-cff9b067455a02de6a042016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 10V, Negative-QTOFsplash10-0a4i-0079000000-5e0da435e9075614bcf42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 20V, Negative-QTOFsplash10-0bwi-0091000000-f18ea79c8ce1382efea82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 40V, Negative-QTOFsplash10-0lec-2190000000-5e89b4135dd0b11d55dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 10V, Positive-QTOFsplash10-0a4i-0019000000-fa17a10e8a34d55baebc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 20V, Positive-QTOFsplash10-0a4l-0198000000-3c7bc5bdeed93fc7e77b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 40V, Positive-QTOFsplash10-01p9-0190000000-54a40d43b14592b5553b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 10V, Negative-QTOFsplash10-0a59-0098000000-d4f29a6ad1adfa42a2382021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 20V, Negative-QTOFsplash10-0bu0-0094000000-8fe6fad8f6880ecc505d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flazine 40V, Negative-QTOFsplash10-00lu-1790000000-7e9c1f226e8cbbbb8f652021-09-24Wishart 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 IDFDB011500
KNApSAcK IDC00050461
Chemspider ID4526683
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5377686
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1835811
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.. .