Bovine Metabolome Database: Showing metabocard for Escitalopram (BMDB0005028)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:14:47 UTC

Update Date

2020-05-11 20:41:18 UTC

BMDB ID

BMDB0005028

Secondary Accession Numbers

BMDB05028

Metabolite Identification

Common Name

Escitalopram

Description

Escitalopram, also known as esertia or cipralex, belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. Escitalopram is a very strong basic compound (based on its pKa). Escitalopram is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Citalopram	ChEBI
(S)-Citalopram	ChEBI
Escitalopramum	ChEBI
Esertia	ChEBI
S(+)-Citalopram	ChEBI
S-(+)-Citalopram	ChEBI
Cipralex	HMDB
Lexapro	HMDB
Cytalopram	HMDB
Citalopram	HMDB
Celexa	HMDB
Citalopram hydrobromide	HMDB
Escitalopram oxalate	HMDB
Seropram	HMDB

Chemical Formula

C₂₀H₂₁FN₂O

Average Molecular Weight

324.3919

Monoisotopic Molecular Weight

324.163791509

IUPAC Name

(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

lexapro

CAS Registry Number

128196-01-0

SMILES

CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1

InChI Key

WSEQXVZVJXJVFP-FQEVSTJZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isocoumaran
Fluorobenzene
Halobenzene
Aralkylamine
Aryl halide
Aryl fluoride
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Carbonitrile
Nitrile
Organoheterocyclic compound
Organic oxygen compound
Organopnictogen compound
Amine
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.58	ALOGPS
logP	3.76	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	35.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6190000000-9c092c583199a2a486ef	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-1497000000-a840cd3176ff240d74f6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0bt9-0692000000-dbd03d31621a5efaba54	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0019000000-84c6ddc8fad411d8541f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1029000000-d4716f92fec4a098ef2c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-5290000000-45334fd57d41c1fadf1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-23521c8b9dc4834c9328	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0091000000-bdb51930294423bb3315	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1590000000-b821092ee64991ad4390	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1029000000-b0f10b0f7897ca083ed5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003r-2294000000-5935fccdd160458bb836	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9740000000-7a3a98de78c385feae56	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-5baf9d241e4712801e87	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3079000000-3efd9cf0f4fddbeed2c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1950000000-69ba9b80f8bec9cbe874	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0005028

DrugBank ID

DB01175

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023596

KNApSAcK ID

Not Available

Chemspider ID

129277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Escitalopram

METLIN ID

Not Available

PubChem Compound

146570

PDB ID

Not Available

ChEBI ID

36791

References

Synthesis Reference

Dall'asta, Leone; Casazza, Umberto; Petersen, Hans. Method for the preparation of citalopram. PCT Int. Appl. (2000), 26 pp. CODEN: PIXXD2 WO 2000023431 A1 20000427 CAN 132:308238 AN 2000:277969

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Escitalopram (BMDB0005028)

Structure for BMDB0005028 (Escitalopram)