Showing Compound Card for 3-azaindole (CDB005615)

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Record Information
Version1.0
Created at2020-04-27 16:38:21 UTC
Updated at2021-01-04 20:37:47 UTC
CannabisDB IDCDB005615
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-azaindole
DescriptionBenzimidazole, also known as 3-azaindole or 1,3-diazaindene, belongs to the class of organic compounds known as benzimidazoles. Benzimidazoles are compounds containing a benzimidazole moiety, which consists of a benzene ring fused to an imidazole. Imidazole is a 5-membered ring consisting of three carbon atoms and two nitrogen atoms at positions 1 and 3 of the imidazole ring. 3-Azaindole or benzimidazole is one of several isomers of azaindazoles that are found in marijuana smoke ( Ref:DOI ). Benzimidazole is formed during the combustion of cannabis. Benzimidazole is a heterocyclic aromatic organic compound. Benzimidazole is a strongly basic compound. This bicyclic compound is a colorless solid. Benzimidazole is produced by condensation of o-phenylenediamine with formic acid (doi:10.15227/orgsyn.019.0012) or the equivalent trimethyl orthoformate. Benzimidazole as been used to create many pharmaceutical drugs such as analgesics, antacids, anti-androgens (used to treat prostate cancer; PMID19145273 ), anti-cancers (PMID: 28544162) and many fungicides. Benzimidazole fungicides have been applied to cereals, fruits, vegetables, and vines since the 1960s and bind to fungal microtubules, inhibiting hyphal growth (PMID: 27686965). Benzimidazole derivatives are among the top frequently used ring systems for small molecule drugs listed by the US FDA (PMID: 24471928).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-BenzodiazoleChEBI
1,3-DiazaindeneChEBI
AzindoleChEBI
BenzoglyoxalineChEBI
HbimChEBI
HbzimChEBI
O-BenzimidazoleChEBI
BenzimidazoleChEBI
Benzimidazole monohydrochlorideMeSH
Benzimidazole mononitrateMeSH
Chemical FormulaC7H6N2
Average Molecular Weight118.14
Monoisotopic Molecular Weight118.0531
IUPAC Name1H-1,3-benzodiazole
Traditional Namebenzimidazole
CAS Registry Number79351-71-6
SMILES
N1C=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
InChI KeyHYZJCKYKOHLVJF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.67ALOGPS
logP1.26ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)12.25ChemAxon
pKa (Strongest Basic)5.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.97 m³·mol⁻¹ChemAxon
Polarizability12.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-azaindole, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-azaindole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1900000000-32b834c70848ea7f1481Spectrum
Predicted GC-MS3-azaindole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-a748760e317519d35edb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-237aaedc281a7c6869af2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-d19bf07c42eb46d0bdc22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-ec0018fe194a581ffd722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9300000000-4dbba5feb460aad641252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-ad44ad5a59274045d6112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-e13078ed71220f011c2d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-4900000000-aaf85c7703530656ac3b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-9200000000-db09859cc86d414cc7042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-ec3b4c31062d629a0e892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-c202fec2faf3ae48abc52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-52d1a9a5355bc378ce3a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-16431851c6c511b8d4162017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-966741cba5b2d1aca7002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-617c630f2de78c87d1302017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-4ca0c3738d04b209f4612017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-2900000000-3fd0f394d6fe39aaae0a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-5900000000-82aeab4fa1e6b14e1abd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014l-9500000000-4db723cb3bf3c8c453d92017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-ab27ee23aeb68d321e422016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-330df0f86f917285f0112016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7900000000-dcc19ff1ab06593e63ba2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-83a328793b3b48ec48f82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-83a328793b3b48ec48f82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-7c7647343faced64607b2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB02962
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02009
BioCyc IDBENZIMIDAZOLE
BiGG IDNot Available
Wikipedia LinkBenzimidazole
METLIN IDNot Available
PubChem Compound5798
PDB IDNot Available
ChEBI ID41275
References
General References
  1. Brawer MK: New treatments for castration-resistant prostate cancer: highlights from the 44th annual meeting of the american society of clinical oncology, may 30-june 3, 2008, chicago, IL. Rev Urol. 2008 Fall;10(4):294-6. [PubMed:19145273 ]