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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:11 UTC
Update Date2019-07-23 06:15:30 UTC
HMDB IDHMDB0034217
Secondary Accession Numbers
  • HMDB34217
Metabolite Identification
Common NameHarmol
DescriptionHarmol, also known as 7-hydroxyharman, 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. Harmol is a chemical compound classified as a β-carboline. Harmol is a very strong basic compound (based on its pKa). Outside of the human body, harmol has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and sea-buckthornberries. This could make harmol a potential biomarker for the consumption of these foods.
Structure
Data?1563862530
Synonyms
ValueSource
1-Methyl-9H-beta-carbolin-7-olHMDB
1-Methyl-9H-pyrido(3,4-b)indol-7-olHMDB
1-Methyl-9H-pyrido[3,4-b]indol-7-olHMDB
1-Methyl-9H-pyrido[3,4-b]indol-7-ol, 9ciHMDB
7-HydroxyharmanHMDB
9H-Pyrido(3,4-b)indol-7-ol, 1-methyl- (8ci)(9ci)HMDB
beta 7-Hydroxy-1-methyl--carbolineHMDB
Chemical FormulaC12H10N2O
Average Molecular Weight198.2206
Monoisotopic Molecular Weight198.079312952
IUPAC Name1-methyl-9H-pyrido[3,4-b]indol-7-ol
Traditional Nameharmol
CAS Registry Number487-03-6
SMILES
CC1=C2NC3=C(C=CC(O)=C3)C2=CC=N1
InChI Identifier
InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,14-15H,1H3
InChI KeySATMZMMKDDTOSQ-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
  • Hydroxyindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point304 - 307 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.84Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.07ALOGPS
logP1.7ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)6.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.91 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57.89 m³·mol⁻¹ChemAxon
Polarizability21.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-b59bea685cca31080e7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0600-3960000000-1033d38ae570f8042b47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8a48c9cd1607d2b939c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-6ef4c1498197971d61f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0900000000-4fd7df78d5e694121c2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b2ecd9a4e9ca62951255Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-8c2c6a9af6d70906a5b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00sj-0900000000-fc47830e60c4afeefe9fSpectrum
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 IDFDB012520
KNApSAcK IDNot Available
Chemspider ID10296888
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHarmol
METLIN IDNot Available
PubChem Compound5280952
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .