Showing metabocard for Sertraline (BMDB0005010)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:35 UTC
Update Date2020-05-11 20:45:53 UTC
BMDB IDBMDB0005010
Secondary Accession Numbers
  • BMDB05010
Metabolite Identification
Common NameSertraline
DescriptionSertraline, also known as CP 51974 or zoloft, belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton. Sertraline is a very strong basic compound (based on its pKa). Sertraline is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-SertralineChEBI
(1S,4S)-SertralineChEBI
(1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamineChEBI
cis-(+)-SertralineChEBI
CP 51974ChEBI
SertralinaChEBI
SertralinumChEBI
Sertraline hydrochlorideHMDB
ZoloftHMDB
BesitranHMDB
Gen sertralineHMDB
Novo sertralineHMDB
Parke davis brand OF sertraline hydrochlorideHMDB
Ratiopharm brand OF sertraline hydrochlorideHMDB
Rhoxal sertralineHMDB
Sertraline hydrochloride (1S-cis)-isomerHMDB
AltrulineHMDB
LustralHMDB
Novo-sertralineHMDB
Rhoxalpharma brand OF sertraline hydrochlorideHMDB
Roerig brand OF sertraline hydrochlorideHMDB
SealdinHMDB
Ratio sertralineHMDB
Ratio-sertralineHMDB
Apo sertralineHMDB
Apo-sertralineHMDB
AremisHMDB
Boehringer ingelheim brand OF sertraline hydrochlorideHMDB
GlademHMDB
Pfizer brand OF sertraline hydrochlorideHMDB
Apotex brand OF sertraline hydrochlorideHMDB
Esteve brand OF sertraline hydrochlorideHMDB
Gen-sertralineHMDB
Genpharm brand OF sertraline hydrochlorideHMDB
Hydrochloride, sertralineHMDB
Lacer brand OF sertraline hydrochlorideHMDB
Novopharm brand OF sertraline hydrochlorideHMDB
Rhoxal-sertralineHMDB
Chemical FormulaC17H17Cl2N
Average Molecular Weight306.23
Monoisotopic Molecular Weight305.073804963
IUPAC Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Traditional Namesertraline
CAS Registry Number79617-96-2
SMILES
CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12
InChI Identifier
InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1
InChI KeyVGKDLMBJGBXTGI-SJCJKPOMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassTametralines
Direct ParentTametralines
Alternative Parents
Substituents
  • Tametraline
  • 1,2-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Secondary aliphatic amine
  • Secondary amine
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organochloride
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.06ALOGPS
logP5.15ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.74 m³·mol⁻¹ChemAxon
Polarizability32.44 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0490000000-724d07a27d5e8d538495View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0091000000-10f81c7fd0a8c096039dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-0980000000-58873180fd0c95a215b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0900000000-35c397f9293e114f3234View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-569e7b0694b3ef81cf90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-2de49c544ebd922028dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-7753c869949091f5c066View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-a995c3f140efa6578777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bt9-2900000000-dee4675a5062129266c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a6r-0950000000-2a9cba59b69c41b10a59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a6r-0950000000-c83a31b55267aefe212aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-dd599a43cebe678e826dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-f3cbee6abbbc3ca370b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-c5202d63a9c4b21b0775View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0910000000-565998e1b2eefa1c2ccbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-fef875b785017dd6bb4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bt9-0900000000-1c524b8999874349f051View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-bf056f6f75a4ccc5d4c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-056r-0980000000-58873180fd0c95a215b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0091000000-10f81c7fd0a8c096039dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0139000000-4f4b68d5ff5484e81ce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1779000000-742a47a4d5d21cc8acb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-1960000000-f03bdc5054705000574cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-d658426c80474367477aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-68fb5194b39f7a3d992bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kwo-4390000000-925d4346a5a2a057e466View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00b9-2890000000-d53a90b04ec8457ad2f1View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005010
DrugBank IDDB01104
Phenol Explorer Compound IDNot Available
FooDB IDFDB023583
KNApSAcK IDNot Available
Chemspider ID61881
KEGG Compound IDC07246
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSertraline
METLIN ID2417
PubChem Compound68617
PDB IDSRE
ChEBI ID9123
References
Synthesis ReferenceCorey, E. J.; Gant, Thomas G. A catalytic enantioselective synthetic route to the important antidepressant sertraline. Tetrahedron Letters (1994), 35(30), 5373-6.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available