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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:09:26 UTC
Update Date2023-02-21 17:17:51 UTC
HMDB IDHMDB0012897
Secondary Accession Numbers
  • HMDB12897
Metabolite Identification
Common Namebeta-Carboline
Descriptionbeta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612 ). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548 ).
Structure
Data?1676999871
Synonyms
ValueSource
2,9-DiazafluoreneChEBI
2-AzacarbazoleChEBI
9H-beta-CarbolineChEBI
9H-Pyrido(3,4-b)indoleChEBI
9H-Pyrido[3,4-b]indoleChEBI
CarbazolineChEBI
NorharmanChEBI
NorharmaneChEBI
9H-b-CarbolineGenerator
9H-Β-carbolineGenerator
b-CarbolineGenerator
Β-carbolineGenerator
Norharman hydrochlorideMeSH, HMDB
NorhormaneMeSH, HMDB
beta-CarbolineHMDB
Chemical FormulaC11H8N2
Average Molecular Weight168.1946
Monoisotopic Molecular Weight168.068748266
IUPAC Name9H-pyrido[3,4-b]indole
Traditional Nameβ-carboline
CAS Registry Number244-63-3
SMILES
N1C2=CC=CC=C2C2=CC=NC=C12
InChI Identifier
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChI KeyAIFRHYZBTHREPW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Indole
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • 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 Point199 °CNot Available
Boiling Point391.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9.55 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.17BIAGI,GL ET AL. (1989)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available132.174http://allccs.zhulab.cn/database/detail?ID=AllCCS00001134
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007945
KNApSAcK IDC00026537
Chemspider ID58486
KEGG Compound IDC20157
BioCyc IDCPD-15304
BiGG IDNot Available
Wikipedia LinkBeta-Carboline
METLIN IDNot Available
PubChem Compound64961
PDB IDNRH
ChEBI ID109895
Food Biomarker OntologyNot Available
VMH IDCE3087
MarkerDB IDNot Available
Good Scents IDrw1269771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hidalgo J, Sanchez-Coronilla A, Balon M, Asuncion Munoz M, Carmona C: Dual emission of temperature-induced betacarboline self-associated hydrogen bond aggregates. Photochem Photobiol Sci. 2009 Mar;8(3):414-20. doi: 10.1039/b816776a. Epub 2009 Jan 20. [PubMed:19255684 ]
  2. Bailey JE, Nutt DJ: GABA-A receptors and the response to CO(2) inhalation - a translational trans-species model of anxiety? Pharmacol Biochem Behav. 2008 Jul;90(1):51-7. doi: 10.1016/j.pbb.2008.04.002. Epub 2008 Apr 9. [PubMed:18485466 ]
  3. Munoz MA, Sama O, Galan M, Guardado P, Carmona C, Balon M: Hydrogen bonding NH/pi interactions between betacarboline and methyl benzene derivatives. Spectrochim Acta A Mol Biomol Spectrosc. 2001 Apr;57A(5):1049-56. [PubMed:11374564 ]
  4. Gynther J, Konschin H, Tylli H, Rouvinen J: Electrostatic requirements for high benzodiazepine receptor affinity among betacarboline-3-carboxylic acid derivatives. Acta Pharm Nord. 1990;2(1):45-52. [PubMed:2160247 ]
  5. Venault P, Chapouthier G: From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory. ScientificWorldJournal. 2007 Feb 19;7:204-23. doi: 10.1100/tsw.2007.48. [PubMed:17334612 ]
  6. Cao R, Peng W, Wang Z, Xu A: beta-Carboline alkaloids: biochemical and pharmacological functions. Curr Med Chem. 2007;14(4):479-500. doi: 10.2174/092986707779940998. [PubMed:17305548 ]