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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:40 UTC
Update Date2021-09-14 15:25:43 UTC
HMDB IDHMDB0061128
Secondary Accession Numbers
  • HMDB61128
Metabolite Identification
Common Name5-Hydroxy, 6-methoxy duloxetine sulfate
Description5-Hydroxy, 6-methoxy duloxetine sulfate belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 5-Hydroxy, 6-methoxy duloxetine sulfate is a very strong basic compound (based on its pKa). 5-Hydroxy, 6-methoxy duloxetine sulfate is a metabolite of duloxetine. Duloxetine (sold under the brand names Cymbalta, Ariclaim, Xeristar, Yentreve, Duzela) is a serotonin-norepinephrine reuptake inhibitor (SNRI) manufactured and marketed by Eli Lilly. It is effective for major depressive disorder and generalized anxiety disorder (GAD).
Structure
Data?1563866149
Synonyms
ValueSource
5-Hydroxy, 6-methoxy duloxetine sulfuric acidGenerator
5-Hydroxy, 6-methoxy duloxetine sulphateGenerator
5-Hydroxy, 6-methoxy duloxetine sulphuric acidGenerator
Chemical FormulaC19H21NO7S
Average Molecular Weight407.438
Monoisotopic Molecular Weight407.103872721
IUPAC Name{5-[1-(furan-2-yl)-3-(methylamino)propoxy]-2-methoxynaphthalen-1-yl}oxidanesulfonic acid
Traditional Name{5-[1-(furan-2-yl)-3-(methylamino)propoxy]-2-methoxynaphthalen-1-yl}oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
[H]C(CCNC)(OC1=C2C=CC(OC)=C(OS(O)(=O)=O)C2=CC=C1)C1=CC=CO1
InChI Identifier
InChI=1S/C19H21NO7S/c1-20-11-10-17(16-7-4-12-25-16)26-15-6-3-5-14-13(15)8-9-18(24-2)19(14)27-28(21,22)23/h3-9,12,17,20H,10-11H2,1-2H3,(H,21,22,23)
InChI KeyBIOIJFFUDCEYJH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Arylsulfate
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Furan
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.048 g/LALOGPS
logP1.46ALOGPS
logP1.19ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.23 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity101.67 m³·mol⁻¹ChemAxon
Polarizability40.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.06931661259
DarkChem[M-H]-193.86631661259
DeepCCS[M+H]+190.94830932474
DeepCCS[M-H]-188.57530932474
DeepCCS[M-2H]-223.02630932474
DeepCCS[M+Na]+198.59930932474
AllCCS[M+H]+194.532859911
AllCCS[M+H-H2O]+191.832859911
AllCCS[M+NH4]+196.932859911
AllCCS[M+Na]+197.632859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-191.132859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxy, 6-methoxy duloxetine sulfate[H]C(CCNC)(OC1=C2C=CC(OC)=C(OS(O)(=O)=O)C2=CC=C1)C1=CC=CO15118.8Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate[H]C(CCNC)(OC1=C2C=CC(OC)=C(OS(O)(=O)=O)C2=CC=C1)C1=CC=CO13129.8Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate[H]C(CCNC)(OC1=C2C=CC(OC)=C(OS(O)(=O)=O)C2=CC=C1)C1=CC=CO13062.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C)C(OC)=CC=C12)C1=CC=CO13176.7Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C)C(OC)=CC=C12)C1=CC=CO13251.3Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C)C(OC)=CC=C12)C1=CC=CO14636.5Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O3322.5Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O3276.9Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O4862.4Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C3300.2Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C3429.3Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C4400.7Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(OC)=CC=C12)C1=CC=CO13424.9Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(OC)=CC=C12)C1=CC=CO13520.2Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #1CNCCC(OC1=CC=CC2=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(OC)=CC=C12)C1=CC=CO14549.2Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O3572.0Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O3473.6Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,1TBDMS,isomer #2COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O4846.2Standard polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TBDMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C3778.5Semi standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TBDMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C3932.7Standard non polar33892256
5-Hydroxy, 6-methoxy duloxetine sulfate,2TBDMS,isomer #1COC1=CC=C2C(OC(CCN(C)[Si](C)(C)C(C)(C)C)C3=CC=CO3)=CC=CC2=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C4385.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9244000000-3a8189114436a01b64b32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 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 - 5-Hydroxy, 6-methoxy duloxetine sulfate 10V, Positive-QTOFsplash10-0a6r-0018900000-2a704673c8bd5869039e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 20V, Positive-QTOFsplash10-054o-7139100000-6e45dcc73dc24e0983a92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 40V, Positive-QTOFsplash10-0fdo-9761000000-59b9cce8c9fd350067282017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 10V, Negative-QTOFsplash10-0a4i-0011900000-32cf5d6c4902a297cf6e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 20V, Negative-QTOFsplash10-07fr-2139100000-d2dcb71304d8849852762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 40V, Negative-QTOFsplash10-000i-6961000000-74803fa1d421826033152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 10V, Positive-QTOFsplash10-0abi-4646900000-b17cdd4ea9a32d494fe92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 20V, Positive-QTOFsplash10-004v-1975000000-7ca10a586c25a7f838d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 40V, Positive-QTOFsplash10-0abl-5931100000-848dd77ebae95bac392f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 10V, Negative-QTOFsplash10-0aor-0080900000-59a483f5a71ba288400b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 20V, Negative-QTOFsplash10-014i-9151100000-4ec968f829816c620ac42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy, 6-methoxy duloxetine sulfate 40V, Negative-QTOFsplash10-014j-9341100000-fea3dde7dee41b896a962021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131770039
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available