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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:51:56 UTC
Update Date2022-03-07 02:56:55 UTC
HMDB IDHMDB0041200
Secondary Accession Numbers
  • HMDB41200
Metabolite Identification
Common NameDehydroxymethylflazine
DescriptionDehydroxymethylflazine 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. Dehydroxymethylflazine is found, on average, in the highest concentration within blackcurrants (Ribes nigrum). Dehydroxymethylflazine has also been detected, but not quantified in, fruits. This could make dehydroxymethylflazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydroxymethylflazine.
Structure
Data?1563863636
Synonyms
ValueSource
1-(2-Furanyl)-9H-pyrido[3,4-b]indole-3-carboxylic acidHMDB
1-(2-Furyl)-9H-pyrido(3,4-b)indole-3-carboxylic acidHMDB
1-(2-Furyl)pyrido(3,4-b)indole-3-carboxylic acidHMDB
1-(Furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylateGenerator
Chemical FormulaC16H10N2O3
Average Molecular Weight278.2622
Monoisotopic Molecular Weight278.069142196
IUPAC Name1-(furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-(furan-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry Number76135-36-9
SMILES
OC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C1
InChI Identifier
InChI=1S/C16H10N2O3/c19-16(20)12-8-10-9-4-1-2-5-11(9)17-14(10)15(18-12)13-6-3-7-21-13/h1-8,17H,(H,19,20)
InChI KeyLTTIWDNLMMLJOI-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
  • Pyridine
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Pyrrole
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.77 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP3.36ALOGPS
logP3.01ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)0.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.35 m³·mol⁻¹ChemAxon
Polarizability28.79 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]+163.85231661259
DarkChem[M-H]-163.45631661259
DeepCCS[M+H]+165.44730932474
DeepCCS[M-H]-163.08930932474
DeepCCS[M-2H]-196.37530932474
DeepCCS[M+Na]+171.60230932474
AllCCS[M+H]+163.132859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+166.832859911
AllCCS[M+Na]+167.832859911
AllCCS[M-H]-164.532859911
AllCCS[M+Na-2H]-163.432859911
AllCCS[M+HCOO]-162.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydroxymethylflazineOC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C13780.4Standard polar33892256
DehydroxymethylflazineOC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C12777.9Standard non polar33892256
DehydroxymethylflazineOC(=O)C1=NC(C2=CC=CO2)=C2NC3=CC=CC=C3C2=C12907.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydroxymethylflazine,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=CO2)=N12959.1Semi standard non polar33892256
Dehydroxymethylflazine,1TMS,isomer #2C[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=CO3)=C212881.4Semi standard non polar33892256
Dehydroxymethylflazine,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C)C1=CC=CC=C212931.5Semi standard non polar33892256
Dehydroxymethylflazine,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C)C1=CC=CC=C212781.7Standard non polar33892256
Dehydroxymethylflazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C([NH]C3=CC=CC=C32)C(C2=CC=CO2)=N13179.7Semi standard non polar33892256
Dehydroxymethylflazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC(C(=O)O)=NC(C3=CC=CO3)=C213115.7Semi standard non polar33892256
Dehydroxymethylflazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C213294.2Semi standard non polar33892256
Dehydroxymethylflazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(C3=CC=CO3)=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C213109.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxymethylflazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0in9-1090000000-b8ac0b7cb732787760822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxymethylflazine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9074000000-1d23a98378bf7f3d140c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydroxymethylflazine 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 - Dehydroxymethylflazine 10V, Positive-QTOFsplash10-01t9-0090000000-7b485c676f0743e63e502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Positive-QTOFsplash10-03fr-0090000000-f66fa3c938036add94972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Positive-QTOFsplash10-0uyr-1190000000-ce52efd1d739765e5d502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Negative-QTOFsplash10-004i-0090000000-a175ebd335accba2b0a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Negative-QTOFsplash10-0560-0090000000-1e69fe205a1f4ffb906a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Negative-QTOFsplash10-0zgj-0090000000-19fdf8160961162351aa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Negative-QTOFsplash10-001i-0090000000-5d8c1b0e4e119c794cb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Negative-QTOFsplash10-001i-0090000000-5d8c1b0e4e119c794cb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Negative-QTOFsplash10-000x-6970000000-2ca9cf1f74528a218f4c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 10V, Positive-QTOFsplash10-004i-0090000000-878b730bb42bf868e9982021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 20V, Positive-QTOFsplash10-01t9-0090000000-cba2dc304071d202ee532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydroxymethylflazine 40V, Positive-QTOFsplash10-01s9-0290000000-3b2cf0f1615ae313628c2021-09-25Wishart 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 IDFDB021099
KNApSAcK IDC00055012
Chemspider ID4589673
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5488120
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1890421
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.. .