AFCDB: Harmol (FDB012520)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:13 UTC

Update date

2019-11-26 03:06:57 UTC

Primary ID

FDB012520

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Harmol

Description

Harmol 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 Number

487-03-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.7	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	6.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	57.89 m³·mol⁻¹	ChemAxon
Polarizability	21.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H10N2O

IUPAC name

1-methyl-9H-pyrido[3,4-b]indol-7-ol

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 Key

SATMZMMKDDTOSQ-UHFFFAOYSA-N

Isomeric SMILES

CC1=C2NC3=C(C=CC(O)=C3)C2=CC=N1

Average Molecular Weight

198.2206

Monoisotopic Molecular Weight

198.079312952

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

an alkaloid (CPD-9941 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 72.71%; H 5.08%; N 14.13%; O 8.07%	DFC
Melting Point	Mp 304-307°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.84	BIOBYTE STARLIST (2009)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	325 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Harmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-0900000000-b59bea685cca31080e7b	Spectrum
Predicted GC-MS	Harmol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0600-3960000000-1033d38ae570f8042b47	Spectrum
Predicted GC-MS	Harmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Harmol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-2793a2b636cbae800fe7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0fr2-0900000000-840d74da55c572209015	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-014i-0900000000-6c60e0c1febf864c4586	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0900000000-3433739210a9a989db84	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0fr2-0900000000-2272c64e070c4d983c32	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-001i-0900000000-f7be6e87d0c6b12b1bbd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e57107b8427991235ec1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-5eaac99880950e42843a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00ea-0900000000-0c5cdea376cf0026e656	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0900000000-6164c97f088c584e13ec	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-cf4644350d7b35b7e988	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0900000000-0b0caa4f33c55d5a79d8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-f84acd3ea336cd158db9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-007k-0900000000-1bed203e72867106ec0b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0900000000-25de019838d10fec4732	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0zpi-1900000000-940f781afeb268c17ce4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-f936c3c05b1041e50bb6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-d4dbc6f248c9a78d0008	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-6670a1adbaf27df44430	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-8a48c9cd1607d2b939c5	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-6ef4c1498197971d61f1	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0900000000-4fd7df78d5e694121c2c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-b2ecd9a4e9ca62951255	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-8c2c6a9af6d70906a5b1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00sj-0900000000-fc47830e60c4afeefe9f	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

10296888

ChEMBL ID

CHEMBL14285

KEGG Compound ID

Not Available

Pubchem Compound ID

68094

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34217

CRC / DFC (Dictionary of Food Compounds) ID

HHR34-N:HHR34-N

EAFUS ID

Not Available

Dr. Duke ID

HARMOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti trypanosomic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Harmol (FDB012520)

Structure for FDB012520 (Harmol)