Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:57 UTC
Primary IDFDB012520
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHarmol
DescriptionHarmol 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 has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and sea-buckthornberries (Hippophae rhamnoides). This could make harmol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Harmol.
CAS Number487-03-6
Structure
Thumb
Synonyms
SynonymSource
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
β-Carboline, 7-hydroxy-1-methyl-biospider
1-Methyl-9H-pyrido[3,4-b]indol-7-ol, 9CIdb_source
9H-Pyrido(3,4-b)indol-7-ol, 1-methyl- (8CI)(9CI)biospider
9H-Pyrido[3,4-b]indol-7-ol, 1-methyl-biospider
Harmoldb_source
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
Chemical FormulaC12H10N2O
IUPAC name1-methyl-9H-pyrido[3,4-b]indol-7-ol
InChI IdentifierInChI=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
Isomeric SMILESCC1=C2NC3=C(C=CC(O)=C3)C2=CC=N1
Average Molecular Weight198.2206
Monoisotopic Molecular Weight198.079312952
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.71%; H 5.08%; N 14.13%; O 8.07%DFC
Melting PointMp 304-307°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.84BIOBYTE STARLIST (2009)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data325 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHarmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0900000000-b59bea685cca31080e7bSpectrum
Predicted GC-MSHarmol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0600-3960000000-1033d38ae570f8042b47Spectrum
Predicted GC-MSHarmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHarmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2793a2b636cbae800fe7Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0fr2-0900000000-840d74da55c572209015Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-014i-0900000000-6c60e0c1febf864c4586Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-3433739210a9a989db84Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0fr2-0900000000-2272c64e070c4d983c32Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001i-0900000000-f7be6e87d0c6b12b1bbdSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e57107b8427991235ec1Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5eaac99880950e42843aSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00ea-0900000000-0c5cdea376cf0026e656Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0900000000-6164c97f088c584e13ecSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-cf4644350d7b35b7e988Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0900000000-0b0caa4f33c55d5a79d8Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-f84acd3ea336cd158db9Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-007k-0900000000-1bed203e72867106ec0bSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0900000000-25de019838d10fec4732Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0zpi-1900000000-940f781afeb268c17ce4Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-f936c3c05b1041e50bb6Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d4dbc6f248c9a78d0008Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6670a1adbaf27df44430Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8a48c9cd1607d2b939c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-6ef4c1498197971d61f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0900000000-4fd7df78d5e694121c2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b2ecd9a4e9ca62951255Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-8c2c6a9af6d70906a5b1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00sj-0900000000-fc47830e60c4afeefe9fSpectrum
NMRNot Available
ChemSpider ID10296888
ChEMBL IDCHEMBL14285
KEGG Compound IDNot Available
Pubchem Compound ID68094
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34217
CRC / DFC (Dictionary of Food Compounds) IDHHR34-N:HHR34-N
EAFUS IDNot Available
Dr. Duke IDHARMOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).