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Record Information
Version4.0
Creation Date2009-07-25 00:01:35 UTC
Update Date2017-09-27 08:27:06 UTC
HMDB IDHMDB0012490
Secondary Accession Numbers
  • HMDB12490
Metabolite Identification
Common Name1,2-Dehydrosalsolinol
Description1,2-dehydrosalsolinol(1-methyl-6,7-dihydroxy-3,4-dihydroisoquinolines) is formed through the decarboxylation of salsolinol-1-carboxylic acid (1-methyl-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid), a novel endogenous catecholic adduct of dopamine and pyruvic acid, examined in nuclei-free homogenates of rat liver, whole brain, and kidney, as well as in buffer only. Liquid chromatographic analysis of incubations for varying times (30 min to 5 h) showed that the tetrahydroisoquinoline substrate decarboxylated oxidatively, forming the DSAL (PMID: 3369867 ). It is involved in Tyrosine Metabolism.
Structure
Thumb
Synonyms
ValueSource
1-Methyl-6,7-dihydroxy-3,4-dihydroisoquinolinesHMDB
3,4-dihydro-1-Methyl-6,7-isoquinolinediolHMDB
DSALHMDB
Chemical FormulaC10H11NO2
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
IUPAC Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
Traditional Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
CAS Registry Number4602-81-7
SMILES
CC1=NCCC2=C1C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C10H11NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-5,12-13H,2-3H2,1H3
InChI KeyDWHSGRLKLUGKOU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dihydroisoquinolines. These are isoquinoline derivatives where exactly two carbon atoms joined by an aromatic bond are linked with a hydrogen atom each, resulting in a CC single bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDihydroisoquinolines
Direct ParentDihydroisoquinolines
Alternative Parents
Substituents
  • Dihydroisoquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP1.19ALOGPS
logP1.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)5.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.69 m³·mol⁻¹ChemAxon
Polarizability18.65 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029097
KNApSAcK IDNot Available
Chemspider ID17960720
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID193796
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Collins MA, Cheng BY: Oxidative decarboxylation of salsolinol-1-carboxylic acid to 1,2-dehydrosalsolinol: evidence for exclusive catalysis by particulate factors in rat kidney. Arch Biochem Biophys. 1988 May 15;263(1):86-95. [PubMed:3369867 ]