Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:35 UTC
Update Date2023-02-21 17:17:50 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
Data?1676999870
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
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydroisoquinolines
Sub ClassNot Available
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.79831661259
DarkChem[M-H]-138.47731661259
DeepCCS[M+H]+139.45430932474
DeepCCS[M-H]-135.62630932474
DeepCCS[M-2H]-173.06230932474
DeepCCS[M+Na]+148.630932474
AllCCS[M+H]+137.532859911
AllCCS[M+H-H2O]+133.032859911
AllCCS[M+NH4]+141.632859911
AllCCS[M+Na]+142.832859911
AllCCS[M-H]-138.632859911
AllCCS[M+Na-2H]-139.132859911
AllCCS[M+HCOO]-139.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2-DehydrosalsolinolCC1=NCCC2=C1C=C(O)C(O)=C22684.2Standard polar33892256
1,2-DehydrosalsolinolCC1=NCCC2=C1C=C(O)C(O)=C21754.5Standard non polar33892256
1,2-DehydrosalsolinolCC1=NCCC2=C1C=C(O)C(O)=C21916.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2-Dehydrosalsolinol,1TMS,isomer #1CC1=NCCC2=CC(O)=C(O[Si](C)(C)C)C=C121824.9Semi standard non polar33892256
1,2-Dehydrosalsolinol,1TMS,isomer #2CC1=NCCC2=CC(O[Si](C)(C)C)=C(O)C=C121851.6Semi standard non polar33892256
1,2-Dehydrosalsolinol,2TMS,isomer #1CC1=NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C121863.5Semi standard non polar33892256
1,2-Dehydrosalsolinol,1TBDMS,isomer #1CC1=NCCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C122103.6Semi standard non polar33892256
1,2-Dehydrosalsolinol,1TBDMS,isomer #2CC1=NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C122111.1Semi standard non polar33892256
1,2-Dehydrosalsolinol,2TBDMS,isomer #1CC1=NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C122328.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dehydrosalsolinol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-1392000000-f1e4a0be2f7e97323ee62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dehydrosalsolinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-0900000000-12d9d22ce9d1f53763a22017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Dehydrosalsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Positive-QTOFsplash10-004i-0900000000-3353063db7785c56ab4b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Positive-QTOFsplash10-002r-1900000000-60a5f8487936dabfac022019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Positive-QTOFsplash10-00vr-7900000000-9a57ee165717efdad1c82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Negative-QTOFsplash10-004i-0900000000-f972bf5f261cc77d06c02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Negative-QTOFsplash10-004i-0900000000-7529c280110b6380588a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Negative-QTOFsplash10-07w9-1900000000-3d8656d3388a0f99e63e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Negative-QTOFsplash10-004i-0900000000-ef6ae59e91e658cf298a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Negative-QTOFsplash10-004i-0900000000-ce3e229270093bb2c74b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Negative-QTOFsplash10-00xr-1900000000-f91c36aaafb986741bf52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Positive-QTOFsplash10-004i-0900000000-287b3d60ee7ac7576fb42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Positive-QTOFsplash10-004i-0900000000-5def6855fd9d71e1370e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Positive-QTOFsplash10-0a4i-4900000000-e69f269d4d26d100a1132021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029097
KNApSAcK IDNot Available
Chemspider ID17960720
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20844
PDB IDNot Available
ChEBI ID193796
Food Biomarker OntologyNot Available
VMH IDCE5629
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]