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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:escitalopram
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Accession:CHEBI:36791 term browser browse the term
Definition:A 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has S-configuration at the chiral centre. It is the active enantiomer of citalopram.
Synonyms:exact_synonym: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
 related_synonym: (+)-citalopram;   (S)-citalopram;   Esertia;   Formula=C20H21FN2O;   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;   InChIKey=WSEQXVZVJXJVFP-FQEVSTJZSA-N;   SMILES=CN(C)CCC[C@]1(OCc2cc(ccc12)C#N)c1ccc(F)cc1;   escitalopramum
 xref: Beilstein:9001444;   CAS:128196-01-0;   DrugBank:DB01175;   Drug_Central:1053;   HMDB:HMDB0005028;   KEGG:D07913;   LINCS:LSM-3569;   PMID:14501259;   PMID:14594439;   PMID:14708881;   PMID:15200745;   PMID:15609164;   PMID:16266205;   PMID:16421462;   PMID:16937393;   PMID:16953656;   PMID:18789789;   PMID:19710642;   PMID:20825390;   PMID:24172161;   PMID:24176515;   PMID:24289655;   PMID:24424469;   PMID:24469525;   PMID:24528284;   Wikipedia:Escitalopram
 cyclic_relationship: is_conjugate_base_of CHEBI:77406;   is_enantiomer_of CHEBI:36792


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citalopram term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcc2 ATP binding cassette subfamily C member 2 increases expression ISO Citalopram results in increased expression of ABCC2 protein CTD PMID:12524417 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Adora1 adenosine A1 receptor multiple interactions ISO [Citalopram co-treated with Caffeine deficiency] results in increased expression of ADORA1 mRNA; [Citalopram co-treated with Caffeine] results in decreased expression of ADORA1 mRNA CTD PMID:29107002 NCBI chr13:51,042,111...51,076,913
Ensembl chr13:51,042,248...51,076,852
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions
decreases expression
ISO Citalopram inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of AHR mRNA]
Citalopram results in decreased expression of AHR mRNA
CTD PMID:24316275 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of AKT1 protein] CTD PMID:30592962 NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G Casp3 caspase 3 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:10487422 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Cat catalase decreases expression ISO Citalopram results in decreased expression of CAT protein CTD PMID:15309392 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Cnr1 cannabinoid receptor 1 decreases expression EXP Citalopram results in decreased expression of CNR1 protein CTD PMID:28866072 NCBI chr 5:49,307,584...49,333,064
Ensembl chr 5:49,311,030...49,333,056
JBrowse link
G Cnr2 cannabinoid receptor 2 increases expression EXP Citalopram results in increased expression of CNR2 protein CTD PMID:28866072 NCBI chr 5:154,242,010...154,268,126
Ensembl chr 5:154,260,062...154,268,126
JBrowse link
G Creb1 cAMP responsive element binding protein 1 multiple interactions ISO Citalopram results in decreased phosphorylation of and results in decreased activity of CREB1 protein CTD PMID:20122921 NCBI chr 9:71,229,753...71,298,994
Ensembl chr 9:71,230,108...71,293,435
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 decreases activity ISO Citalopram results in decreased activity of CYP19A1 protein CTD PMID:26162595 NCBI chr 8:58,744,849...58,772,408
Ensembl chr 8:58,744,849...58,772,408
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases methylation ISO CYP2C19 protein polymorphism results in decreased methylation of Citalopram; CYP2C19 protein results in decreased methylation of Citalopram analog CTD PMID:9110356, PMID:12975335 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 decreases methylation ISO CYP2D6 protein results in decreased methylation of Citalopram analog CTD PMID:9110356 NCBI chr 7:123,599,264...123,608,436
Ensembl chr 7:123,599,266...123,608,436
JBrowse link
G Dbh dopamine beta-hydroxylase multiple interactions ISO DBH protein promotes the reaction [Citalopram results in increased abundance of Serotonin] CTD PMID:15148402 NCBI chr 3:5,709,236...5,731,895
Ensembl chr 3:5,709,236...5,731,898
JBrowse link
G Dnmt1 DNA methyltransferase 1 affects expression EXP Citalopram affects the expression of DNMT1 mRNA CTD PMID:21682946 NCBI chr 8:21,922,515...21,968,495
Ensembl chr 8:21,922,515...21,968,495
JBrowse link
G Dnmt3a DNA methyltransferase 3 alpha affects expression EXP Citalopram affects the expression of DNMT3A mRNA CTD PMID:21682946 NCBI chr 6:28,205,375...28,346,052
Ensembl chr 6:28,235,695...28,340,577
JBrowse link
G Fabp1 fatty acid binding protein 1 increases expression ISO Citalopram results in increased expression of FABP1 mRNA CTD PMID:17567588 NCBI chr 4:99,063,181...99,066,957
Ensembl chr 4:99,063,181...99,066,954
JBrowse link
G Fcer1g Fc fragment of IgE receptor Ig multiple interactions ISO Citalopram inhibits the reaction [convulxin promotes the reaction [FCER1G protein binds to SYK protein]] CTD PMID:30592962 NCBI chr13:89,601,894...89,606,326
Ensembl chr13:89,601,896...89,606,326
JBrowse link
G Gdpd3 glycerophosphodiester phosphodiesterase domain containing 3 increases expression ISO Citalopram results in increased expression of GDPD3 mRNA CTD PMID:17567588 NCBI chr 1:198,199,032...198,209,178
Ensembl chr 1:198,199,622...198,209,150
JBrowse link
G Gria1 glutamate ionotropic receptor AMPA type subunit 1 affects response to substance ISO GRIA1 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr10:42,441,723...42,760,200
Ensembl chr10:42,614,713...42,760,200
JBrowse link
G Gria3 glutamate ionotropic receptor AMPA type subunit 3 affects response to substance ISO GRIA3 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr  X:127,561,843...127,829,763
Ensembl chr  X:127,562,660...127,829,753
JBrowse link
G Grik2 glutamate ionotropic receptor kainate type subunit 2 affects response to substance ISO GRIK2 polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr20:53,791,428...54,517,691
Ensembl chr20:53,789,760...54,517,709
JBrowse link
G Grin2b glutamate ionotropic receptor NMDA type subunit 2B decreases expression EXP Citalopram results in decreased expression of GRIN2B protein CTD PMID:23260230 NCBI chr 4:169,541,620...170,000,216
Ensembl chr 4:169,560,387...169,999,873
JBrowse link
G Grin3a glutamate ionotropic receptor NMDA type subunit 3A affects response to substance ISO GRIN3A polymorphism affects the susceptibility to Citalopram CTD PMID:19295509 NCBI chr 5:64,928,620...65,073,012
Ensembl chr 5:64,928,620...65,073,012
JBrowse link
G Hmgcs1 3-hydroxy-3-methylglutaryl-CoA synthase 1 increases expression ISO Citalopram results in increased expression of HMGCS1 mRNA CTD PMID:16324787 NCBI chr 2:52,427,351...52,445,082
Ensembl chr 2:52,431,601...52,445,055
JBrowse link
G Htr1b 5-hydroxytryptamine receptor 1B decreases expression EXP Citalopram results in decreased expression of HTR1B protein CTD PMID:18157704 NCBI chr 8:89,113,984...89,130,830
Ensembl chr 8:89,129,453...89,130,991
JBrowse link
G Htr2c 5-hydroxytryptamine receptor 2C affects binding ISO Citalopram binds to HTR2C protein CTD PMID:18083778 NCBI chr  X:118,084,520...118,318,040
Ensembl chr  X:118,084,890...118,318,039
JBrowse link
G Inhbe inhibin subunit beta E increases expression ISO Citalopram results in increased expression of INHBE mRNA CTD PMID:17567588 NCBI chr 7:70,641,423...70,642,848
Ensembl chr 7:70,640,075...70,643,169
JBrowse link
G Lat linker for activation of T cells multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of LAT protein] CTD PMID:30592962 NCBI chr 1:197,765,644...197,770,669
Ensembl chr 1:197,765,644...197,770,669
JBrowse link
G Npvf neuropeptide VF precursor affects expression ISO Citalopram affects the expression of NPVF mRNA CTD PMID:20381503 NCBI chr 4:80,391,785...80,395,476
Ensembl chr 4:80,391,785...80,395,502
JBrowse link
G Nr3c1 nuclear receptor subfamily 3, group C, member 1 multiple interactions ISO Citalopram inhibits the reaction [Dexamethasone results in increased expression of NR3C1 mRNA] CTD PMID:24316275 NCBI chr18:31,728,373...32,704,022
Ensembl chr18:31,728,373...31,749,647
JBrowse link
G Ntrk2 neurotrophic receptor tyrosine kinase 2 multiple interactions ISO Citalopram results in increased phosphorylation of and results in increased activity of NTRK2 protein CTD PMID:21666748 NCBI chr17:5,934,651...6,245,778
Ensembl chr17:5,933,729...6,244,676
JBrowse link
G Nupr1 nuclear protein 1, transcriptional regulator increases expression ISO Citalopram results in increased expression of NUPR1 mRNA CTD PMID:17567588 NCBI chr 1:194,767,484...194,769,519
Ensembl chr 1:194,767,474...194,769,524
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Citalopram results in increased cleavage of PARP1 protein CTD PMID:10487422 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Pomc proopiomelanocortin increases expression ISO Citalopram results in increased expression of POMC protein CTD PMID:20414043 NCBI chr 6:28,382,937...28,388,771
Ensembl chr 6:28,382,962...28,388,967
JBrowse link
G Prkcd protein kinase C, delta multiple interactions ISO Citalopram inhibits the reaction [convulxin results in increased phosphorylation of PRKCD protein] CTD PMID:30592962 NCBI chr16:6,655,131...6,675,746
Ensembl chr16:6,655,120...6,675,746
JBrowse link
G Prl prolactin affects secretion
multiple interactions
increases expression
ISO Citalopram affects the secretion of PRL protein
SLC6A4 polymorphism inhibits the reaction [Citalopram affects the secretion of PRL protein]
Citalopram results in increased expression of PRL protein
CTD PMID:17000009, PMID:19153152 NCBI chr17:39,814,236...39,824,299
Ensembl chr17:39,814,244...39,824,299
JBrowse link
G S100a10 S100 calcium binding protein A10 affects expression EXP Citalopram affects the expression of S100A10 mRNA CTD PMID:21682946 NCBI chr 2:193,892,589...193,901,236
Ensembl chr 2:193,892,589...193,901,236
JBrowse link
G Scd stearoyl-CoA desaturase increases expression ISO Citalopram results in increased expression of SCD mRNA CTD PMID:16324787 NCBI chr 1:264,159,966...264,173,061
Ensembl chr 1:264,160,129...264,172,729
JBrowse link
G Serpina3m serpin family A member 3M increases expression ISO Citalopram results in increased expression of SERPINA3 mRNA CTD PMID:17567588 NCBI chr 6:127,808,785...127,816,067
Ensembl chr 6:127,808,785...127,816,055
JBrowse link
G Slc2a3 solute carrier family 2 member 3 decreases expression ISO Citalopram results in decreased expression of SLC2A3 mRNA CTD PMID:17567588 NCBI chr 4:155,549,991...155,626,018
Ensembl chr 4:155,408,233...155,631,856
JBrowse link
G Slc32a1 solute carrier family 32 member 1 decreases expression EXP Citalopram results in decreased expression of SLC32A1 protein CTD PMID:20707986 NCBI chr 3:155,102,980...155,107,815
Ensembl chr 3:155,103,150...155,107,817
JBrowse link
G Slc6a15 solute carrier family 6 member 15 multiple interactions ISO [Citalopram co-treated with Caffeine] results in decreased expression of SLC6A15 mRNA CTD PMID:29107002 NCBI chr 7:45,328,207...45,381,920
Ensembl chr 7:45,328,105...45,382,229
JBrowse link
G Slc6a3 solute carrier family 6 member 3 multiple interactions
affects response to substance
ISO SLC6A3 mutant form promotes the reaction [Citalopram results in increased abundance of Dopamine]
[SLC6A3 protein polymorphism affects the susceptibility to Citalopram] which affects the uptake of Dopamine; Citalopram inhibits the reaction [SLC6A3 protein results in increased uptake of Dopamine]
CTD PMID:14691264, PMID:31009648 NCBI chr 1:32,323,011...32,363,983
Ensembl chr 1:32,321,580...32,363,983
JBrowse link
G Slc6a4 solute carrier family 6 member 4 multiple interactions
affects response to substance
ISO Citalopram binds to and results in decreased activity of SLC6A4 protein; Citalopram inhibits the reaction [convulxin promotes the reaction [SLC6A4 protein binds to SYK protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Dopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Methamphetamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Octopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [tryptamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Tyramine results in increased activity of TAAR1 protein]]; SLC6A4 polymorphism inhibits the reaction [Citalopram affects the secretion of PRL protein]
SLC6A4 promoter polymorphism affects the susceptibility to Citalopram
CTD PMID:14624186, PMID:16272152, PMID:17000009, PMID:17234900, PMID:30592962 NCBI chr10:63,153,656...63,188,377
Ensembl chr10:63,153,651...63,176,463
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of SREBF1 protein CTD PMID:16324787 NCBI chr10:46,570,996...46,593,021
Ensembl chr10:46,570,996...46,593,009
JBrowse link
G Srebf2 sterol regulatory element binding transcription factor 2 multiple interactions ISO Citalopram results in increased cleavage of and results in increased activity of SREBF2 protein CTD PMID:16324787 NCBI chr 7:123,381,082...123,438,605
Ensembl chr 7:123,381,077...123,438,603
JBrowse link
G Syk spleen associated tyrosine kinase multiple interactions ISO Citalopram inhibits the reaction [convulxin promotes the reaction [FCER1G protein binds to SYK protein]]; Citalopram inhibits the reaction [convulxin promotes the reaction [SLC6A4 protein binds to SYK protein]]; Citalopram inhibits the reaction [convulxin results in increased phosphorylation of SYK protein] CTD PMID:30592962 NCBI chr17:12,614,311...12,669,568
Ensembl chr17:12,614,311...12,669,573
JBrowse link
G Taar1 trace-amine-associated receptor 1 multiple interactions ISO Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Dopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Methamphetamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Octopamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [tryptamine results in increased activity of TAAR1 protein]]; Citalopram inhibits the reaction [SLC6A4 protein promotes the reaction [Tyramine results in increased activity of TAAR1 protein]] CTD PMID:17234900 NCBI chr 1:22,595,477...22,596,475
Ensembl chr 1:22,595,477...22,596,475
JBrowse link
G Tagln transgelin decreases expression ISO Citalopram results in decreased expression of TAGLN mRNA CTD PMID:17567588 NCBI chr 8:50,222,895...50,228,369
Ensembl chr 8:50,222,896...50,231,357
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    chemical entity 19787
      group 19698
        pseudohalo group 2882
          cyano group 2882
            nitrile 2882
              1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile 49
                escitalopram 49
                  citalopram 49
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    main group molecular entity 19672
                      s-block molecular entity 19430
                        hydrogen molecular entity 19420
                          hydrides 18686
                            inorganic hydride 17411
                              pnictogen hydride 17383
                                nitrogen hydride 17224
                                  azane 16941
                                    ammonia 16940
                                      organic amino compound 16939
                                        tertiary amino compound 8630
                                          1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile 49
                                            escitalopram 49
                                              citalopram 49
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