Norharman (CHEM016379)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:29:36 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016379
Identification
Common NameNorharman
ClassSmall Molecule
DescriptionThe parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass168.195 g/mol
Monoisotopic Mass168.069 g/mol
CAS Registry Number244-63-3
IUPAC Name9H-pyrido[3,4-b]indole
Traditional Nameβ-carboline
SMILESN1C2=CC=CC=C2C2=C1C=NC=C2
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.56ALOGPS
logP1.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.22ChemAxon
pKa (Strongest Basic)5.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.32 m³·mol⁻¹ChemAxon
Polarizability18.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0900000000-fcdb4b3e6837a47248e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-5f1c82b770634430089fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-ec1e052158bb7ac51fa5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 11V, negativesplash10-014i-0900000000-8356e3b21f024042498fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 15V, negativesplash10-014i-0900000000-309bca0da39eb9bfe16cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 21V, negativesplash10-014i-0900000000-5a054045fb18991566adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-014i-0900000000-6ae41f21021169fba158Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-014l-0900000000-18f3f6cb6eddcab3e38cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-03di-9000000000-eebba0b8b6a195a9bcf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, negativesplash10-014i-0900000000-bb0bad9db10636d0020aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-014i-0900000000-81c9902ae9712620ee7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-014i-0900000000-2ff64ee76e6f4e6e7b47Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-014i-0900000000-eb22bb403f17b41824eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-014i-0900000000-710549ac9a89ddcb850fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-014l-0900000000-0560d33cc2baa8568068Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-014i-1900000000-e89060680f0fbbb90fc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-7bfe2973a911f7d04882Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-c64bc52da34801ce4cf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-730c48ee2c09863f6c4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c27561fcfb62e1fb8dc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-eb27fd1af093e9373987Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-675b8bf1bb9442b351a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-6b01d3bcbbc7303b646bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a18ea037f074412ab5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-d9a1aef47a4155b550a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-82fd47fe0f1bc435ec2cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012897
FooDB IDFDB007945
Phenol Explorer IDNot Available
KNApSAcK IDC00026537
BiGG IDNot Available
BioCyc IDCPD-15304
METLIN IDNot Available
PDB IDNRH
Wikipedia LinkBeta-Carboline
Chemspider ID58486
ChEBI ID109895
PubChem Compound ID64961
Kegg Compound IDC20157
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23600147
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8070089
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.