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
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