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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:09:26 UTC
Update Date2019-01-11 19:31:53 UTC
HMDB IDHMDB0012897
Secondary Accession Numbers
  • HMDB12897
Metabolite Identification
Common NameBeta-Carboline
Descriptionb-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as b-carbolines.
Structure
Data?1547235113
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
b-CarbolineGenerator
β-carbolineGenerator
9H-b-CarbolineGenerator
9H-β-carbolineGenerator
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=C1C=NC=C2
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
DescriptionThis compound belongs to the class of organic compounds known as beta carbolines. These 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.17BIAGI,GL ET AL. (1989)
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 RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0900000000-fcdb4b3e6837a47248e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-5f1c82b770634430089fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-ec1e052158bb7ac51fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-eb27fd1af093e9373987View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-675b8bf1bb9442b351a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-6b01d3bcbbc7303b646bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a18ea037f074412ab5bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-d9a1aef47a4155b550a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-82fd47fe0f1bc435ec2cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (6 - 18 years old)Bothenthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
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 ]