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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:dextromethadone
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Accession:CHEBI:167308 term browser browse the term
Definition:A 6-(dimethylamino)-4,4-diphenylheptan-3-one that has (S)-configuration. It is the less active enantiomer of methadone and has very little activity on opioid receptors and mainly responsible for the inhibition of hERG K+ channels and thus for cardiac toxicity. The drug is currently under clinical development for the treatment of major depressive disorder.
Synonyms:exact_synonym: (6S)-6-(dimethylamino)-4,4-diphenylheptan-3-one
 related_synonym: (+)-methadone;   (6S)-methadone;   (S)-6-(dimethylamino)-4,4-diphenyl-3-heptanone;   Formula=C21H27NO;   InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3/t17-/m0/s1;   InChIKey=USSIQXCVUWKGNF-KRWDZBQOSA-N;   REL-1017;   S-methadone;   SMILES=CCC(=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1;   d-6-(dimethylamino)-4,4-diphenyl-3-heptanone;   d-methadone
 xref: CAS:5653-80-5;   Chemspider:559067;   DrugBank:DB15198;   PMID:21175445;   PMID:23249875;   PMID:23935979;   PMID:27055456;   PMID:27456067;   PMID:27974484;   PMID:29458047;   PMID:30907440;   PMID:31091116;   PMID:31368772;   PMID:31454827;   PMID:32302325;   PMID:33345336;   Reaxys:3213667;   Wikipedia:Dextromethadone
 cyclic_relationship: is_enantiomer_of CHEBI:136003



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methadone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases expression
affects activity
ISO Methadone results in increased expression of ABCB1 protein
Methadone affects the activity of ABCB1 protein
CTD PMID:19840843 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
JBrowse link
G Abcb1b ATP-binding cassette, subfamily B (MDR/TAP), member 1B affects activity
increases expression
EXP Methadone affects the activity of ABCB1B protein
Methadone results in increased expression of ABCB1B protein
CTD PMID:19840843 NCBI chr 4:25,242,761...25,325,194
Ensembl chr 4:25,242,798...25,325,199
JBrowse link
G Bax BCL2 associated X, apoptosis regulator affects localization ISO Methadone affects the localization of BAX protein CTD PMID:20691259 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 increases secretion EXP Methadone results in increased secretion of CCL2 protein CTD PMID:20178837 NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
JBrowse link
G Ccl3 C-C motif chemokine ligand 3 increases secretion EXP Methadone results in increased secretion of CCL3 protein CTD PMID:20178837 NCBI chr10:68,451,388...68,452,938
Ensembl chr10:68,451,388...68,452,938
JBrowse link
G Cx3cl1 C-X3-C motif chemokine ligand 1 increases secretion EXP Methadone results in increased secretion of CX3CL1 protein CTD PMID:20178837 NCBI chr19:10,227,337...10,237,826
Ensembl chr19:10,227,340...10,236,833
JBrowse link
G Cxcl1 C-X-C motif chemokine ligand 1 increases secretion EXP Methadone results in increased secretion of CXCL1 protein CTD PMID:20178837 NCBI chr14:17,193,364...17,195,143
Ensembl chr14:17,193,365...17,195,215
JBrowse link
G Cycs cytochrome c, somatic affects localization ISO Methadone affects the localization of CYCS protein CTD PMID:20691259 NCBI chr 4:79,651,894...79,653,994
Ensembl chr 4:79,651,378...79,654,054
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 multiple interactions
affects metabolic processing
ISO Aminoglutethimide inhibits the reaction [CYP19A1 protein affects the metabolism of Methadone]; formestane inhibits the reaction [CYP19A1 protein affects the metabolism of Methadone] CTD PMID:15242824 NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 increases metabolic processing
decreases activity
ISO CYP2D22 protein results in increased metabolism of Methadone
Methadone results in decreased activity of CYP2D6 protein
CTD PMID:16595712 NCBI chr 7:113,882,584...113,891,754
Ensembl chr 7:113,881,618...113,891,759
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 affects metabolic processing
increases metabolic processing
ISO CYP3A4 protein affects the metabolism of Methadone
CYP3A4 protein results in increased metabolism of Methadone
CTD PMID:15986265 PMID:16595712 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Drd2 dopamine receptor D2 multiple interactions EXP Methadone affects the reaction [Cocaine affects the expression of DRD2 mRNA] CTD PMID:18990547 NCBI chr 8:49,708,903...49,772,888
Ensembl chr 8:49,708,927...49,772,875
JBrowse link
G Hcrt hypocretin neuropeptide precursor multiple interactions EXP Methadone affects the reaction [Cocaine affects the expression of HCRT mRNA] CTD PMID:18990547 NCBI chr10:85,689,992...85,691,206
Ensembl chr10:85,689,465...85,691,210
JBrowse link
G Il10 interleukin 10 increases secretion EXP Methadone results in increased secretion of IL10 protein CTD PMID:20178837 NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
JBrowse link
G Il1a interleukin 1 alpha increases expression EXP Methadone results in increased expression of IL1A protein CTD PMID:20178837 NCBI chr 3:116,526,601...116,537,055
Ensembl chr 3:116,526,604...116,536,822
JBrowse link
G Il1b interleukin 1 beta increases secretion
increases expression
EXP Methadone results in increased secretion of IL1B protein
Methadone results in increased expression of IL1B protein
CTD PMID:20178837 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
JBrowse link
G Il2 interleukin 2 decreases expression ISO Methadone results in decreased expression of IL2 mRNA CTD PMID:23965172 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
JBrowse link
G Il4 interleukin 4 increases expression
multiple interactions
ISO Methadone results in increased expression of IL4 mRNA; Methadone results in increased expression of IL4 protein
CTAP octapeptide inhibits the reaction [Methadone results in increased expression of IL4 mRNA]; SB 203580 inhibits the reaction [Methadone results in increased expression of IL4 mRNA]
CTD PMID:23965172 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
JBrowse link
G Il6 interleukin 6 increases expression
increases secretion
EXP Methadone results in increased expression of IL6 mRNA; Methadone results in increased expression of IL6 protein
Methadone results in increased secretion of IL6 protein
CTD PMID:20178837 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Ins2 insulin 2 decreases response to substance ISO Methadone results in decreased susceptibility to INS protein CTD PMID:2554359 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
JBrowse link
G Kcnh2 potassium voltage-gated channel subfamily H member 2 multiple interactions
decreases activity
ISO Chlorobutanol promotes the reaction [Methadone results in decreased activity of KCNH2 protein] CTD PMID:14527710 NCBI chr 4:10,826,834...10,859,009
Ensembl chr 4:10,826,928...10,859,008
JBrowse link
G Lep leptin increases expression ISO Methadone results in increased expression of LEP protein CTD PMID:15717844 NCBI chr 4:57,661,127...57,675,262
Ensembl chr 4:57,661,131...57,675,262
JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO Methadone results in increased phosphorylation of MAPK1 protein CTD PMID:23965172 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation ISO Methadone results in increased phosphorylation of MAPK3 protein CTD PMID:23965172 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Nfkbia NFKB inhibitor alpha increases expression ISO Methadone results in increased expression of NFKBIA protein CTD PMID:22258905 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
JBrowse link
G Oprd1 opioid receptor, delta 1 affects binding
multiple interactions
EXP Methadone binds to OPRD1 protein
[Methadone binds to OPRD1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRD1 protein] which results in decreased uptake of Serotonin
CTD PMID:7562497 NCBI chr 5:144,306,188...144,340,960
Ensembl chr 5:144,306,188...144,340,960
JBrowse link
G Oprk1 opioid receptor, kappa 1 affects binding
multiple interactions
EXP Methadone binds to OPRK1 protein
[Methadone binds to OPRK1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRK1 protein] which results in decreased uptake of Serotonin
CTD PMID:7562497 NCBI chr 5:13,860,016...13,877,823
Ensembl chr 5:13,860,021...13,877,823
JBrowse link
G Oprm1 opioid receptor, mu 1 multiple interactions
affects binding
EXP [Methadone binds to OPRM1 protein] which results in decreased uptake of Norepinephrine; [Methadone binds to OPRM1 protein] which results in decreased uptake of Serotonin CTD PMID:7562497 NCBI chr 1:43,160,057...43,413,409
Ensembl chr 1:43,160,057...43,413,409
JBrowse link
G Pld2 phospholipase D2 increases activity ISO Methadone results in increased activity of PLD2 protein CTD PMID:23965172 NCBI chr10:55,256,326...55,274,192
Ensembl chr10:55,256,359...55,272,808
JBrowse link
G Prl prolactin affects secretion
increases secretion
increases expression
ISO Methadone affects the secretion of PRL protein
Methadone results in increased secretion of PRL protein
Methadone results in increased expression of PRL protein
CTD PMID:2554359 PMID:16675813 PMID:21094671 NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062
JBrowse link
G Tlr4 toll-like receptor 4 affects binding
increases expression
affects response to substance
multiple interactions
ISO
EXP
Methadone binds to TLR4 protein
Methadone results in increased expression of TLR4 mRNA; Methadone results in increased expression of TLR4 protein
Methadone affects the susceptibility to TLR4 protein
Naloxone affects the reaction [Methadone binds to TLR4 protein]
CTD PMID:20178837 NCBI chr 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628
JBrowse link
G Tnf tumor necrosis factor increases secretion
increases expression
EXP Methadone results in increased secretion of TNF protein
Methadone results in increased expression of TNF protein
CTD PMID:20178837 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19795
    role 19746
      biological role 19746
        pharmacological role 18832
          analgesic 13307
            opioid analgesic 637
              dextromethadone 32
                methadone + 32
Path 2
Term Annotations click to browse term
  CHEBI ontology 19795
    subatomic particle 19794
      composite particle 19794
        hadron 19794
          baryon 19794
            nucleon 19794
              atomic nucleus 19794
                atom 19794
                  main group element atom 19693
                    p-block element atom 19693
                      carbon group element atom 19614
                        carbon atom 19604
                          organic molecular entity 19604
                            organic group 18713
                              organic divalent group 18697
                                organodiyl group 18697
                                  carbonyl group 18646
                                    carbonyl compound 18646
                                      ketone 16955
                                        dialkyl ketone 46
                                          heptan-3-one 32
                                            6-(dimethylamino)-4,4-diphenylheptan-3-one 32
                                              dextromethadone 32
                                                methadone + 32
paths to the root