Human Metabolome Database: Showing metabocard for Citalopram propionic acid (HMDB0060463)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:34 UTC

Update Date

2017-12-20 20:31:03 UTC

HMDB ID

HMDB0060463

Secondary Accession Numbers

HMDB60463

Metabolite Identification

Common Name

Citalopram propionic acid

Description

Citalopram propionic acid is a metabolite of citalopram. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. It has U.S. Food and Drug Administration (FDA) approval to treat major depression, and is prescribed off-label for a number of anxiety conditions. (Wikipedia)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₁₈H₁₄FNO₃

Average Molecular Weight

311.3071

Monoisotopic Molecular Weight

311.095771524

IUPAC Name

3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid

Traditional Name

citalopram propionic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C18H14FNO3/c19-15-4-2-14(3-5-15)18(8-7-17(21)22)16-6-1-12(10-20)9-13(16)11-23-18/h1-6,9H,7-8,11H2,(H,21,22)

InChI Key

JSYNRZJODZWUKX-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as isocoumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Oxacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nitrile (CHEBI:80605 )
benzenes (CHEBI:80605 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Process

Naturally occurring process:

Physical Properties

State

Not Available

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
Water Solubility	0.0055 g/L	ALOGPS
logP	2.88	ALOGPS
logP	3.17	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.03 m³·mol⁻¹	ChemAxon
Polarizability	30.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	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-0190000000-3d06e9999ac297d7ff75	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-2190000000-85bbf7d086d9c3730e81	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0097000000-a4cc60c1a67d15d9c509	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02u3-0191000000-32bf56429ae77a046a9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3690000000-f1889e924027df9a1682	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0039000000-205792dd03a321acfcea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1097000000-57e6d8b00468c04d0b19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003b-3190000000-9d9fff6b255b7514f399	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Location

Kidney
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Citalopram Action Pathway		Not Available
Citalopram Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Urine	Expected but not Quantified		Not Available	Not Available	Normal		details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16610

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10403174

PDB ID

Not Available

ChEBI ID

80605

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Reactions

Citalopram aldehyde + Water + Oxygen → Citalopram propionic acid + Hydrogen peroxide	details

Showing metabocard for Citalopram propionic acid (HMDB0060463)

Structure for HMDB0060463 (Citalopram propionic acid)

Enzymes

Reactions