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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:02:51 UTC
Update Date2019-07-23 06:15:33 UTC
HMDB IDHMDB0034244
Secondary Accession Numbers
  • HMDB34244
Metabolite Identification
Common NameIsoquinoline
DescriptionIsoquinoline is a flavouring agent Being an analog of pyridine, isoquinoline is a weak base, with a pKb of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative. Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine and morphine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine
Structure
Data?1563862533
Synonyms
ValueSource
2-BenzazineChEBI
Benzo[c]pyridineChEBI
IsochinolinChEBI
2-AzanaphthaleneHMDB
2-BenzanineHMDB
3,4-BenzopyridineHMDB
Benzo(c)pyridineHMDB
BenzopyridineHMDB
beta -QuinolineHMDB
beta-QuinolineHMDB
FEMA 2978HMDB
ISQHMDB
Isoquinoline sulfate (1:1)HMDB
Isoquinoline hydrobromideHMDB
Isoquinoline hydrochlorideHMDB
Isoquinoline hydroiodideHMDB
Isoquinoline conjugate acidHMDB
Chemical FormulaC9H7N
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
IUPAC Nameisoquinoline
Traditional Nameisoquinoline
CAS Registry Number119-65-3
SMILES
C1=CC=C2C=NC=CC2=C1
InChI Identifier
InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
InChI KeyAWJUIBRHMBBTKR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassNot Available
Direct ParentIsoquinolines and derivatives
Alternative Parents
Substituents
  • Isoquinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point25.5 - 26 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.52 mg/mL at 25 °CNot Available
LogP2.08Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.81 g/LALOGPS
logP2.14ALOGPS
logP1.75ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.35 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-153cb7989d20a5d305feSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-938e708f6f6371c89a90Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-153cb7989d20a5d305feSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-938e708f6f6371c89a90Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-0900000000-58fc23546d7bc648aaffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-fe8f7e7494fe51834c73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-53932d6a797b58065acfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-3bd6daf754e7fa1a6223Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-7900000000-c5e6dca63fceb0eb257aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-a4927588bd0391d5e768Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-43576b7775a986b95c7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ba509566033d258bb64Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a52113b66ca5a059f497Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-1631e63f0b49a1687150Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0f89-0900000000-95ee1aa2d6255c9ec936Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0ugi-4900000000-1dd979c3c8f2435edd6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9800000000-d91870148f53fbc1391aSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-bca894ecef9e1b2fb95eSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-aa2de101cd67d3fcfd39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-d3baf54cc19e70a1ec07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f58afd1811d8a3a4d0d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1900000000-4a2becbb485199b25f49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b4be2f7dd0aed898ee51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-b2a468601694a7ca84beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-416ad6650d560fd35318Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04329
Phenol Explorer Compound IDNot Available
FooDB IDFDB012557
KNApSAcK IDNot Available
Chemspider ID8098
KEGG Compound IDC06323
BioCyc IDISOQUINOLINE
BiGG IDNot Available
Wikipedia LinkIsoquinoline
METLIN IDNot Available
PubChem Compound8405
PDB IDISQ
ChEBI ID16092
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Candenas ML, Naline E, D'Ocon MP, Cortes D, Advenier C: Effects of cularine and other isoquinoline alkaloids on guinea-pig trachea and human bronchus. J Pharm Pharmacol. 1990 Feb;42(2):102-7. [PubMed:1972394 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .