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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:yohimbine
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Accession:CHEBI:10093 term browser browse the term
Definition:An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.
Synonyms:exact_synonym: methyl 17alpha-hydroxyyohimban-16alpha-carboxylate
 related_synonym: (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester;   17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester;   Formula=C21H26N2O3;   InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1;   InChIKey=BLGXFZZNTVWLAY-SCYLSFHTSA-N;   Johimbin;   Quebrachin;   SMILES=[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCc3c1[nH]c1ccccc31)C2;   Yohimbin;   aphrodine;   corynine;   quebrachine;   yohimbic acid methyl ester
 xref: Beilstein:4720812;   Beilstein:97276;   CAS:146-48-5;   DrugBank:DB01392;   Drug_Central:3659;   KEGG:C09256;   KEGG:D08685;   KNApSAcK:C00001789;   LINCS:LSM-2779
 xref_mesh: MESH:D015016
 xref: VSDB:3010


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yohimbine 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 ISO Yohimbine analog results in increased expression of ABCB1 mRNA CTD PMID:7476894 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Abcb4 ATP binding cassette subfamily B member 4 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of ABCB4 mRNA CTD PMID:28843594 NCBI chr 4:22,133,984...22,192,687
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of ABCC2 mRNA CTD PMID:28843594 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Abcc3 ATP binding cassette subfamily C member 3 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of ABCC3 mRNA CTD PMID:28843594 NCBI chr10:82,047,308...82,116,928
Ensembl chr10:82,047,863...82,117,109
JBrowse link
G Actg1 actin, gamma 1 increases expression EXP Yohimbine results in increased expression of ACTG1 mRNA CTD PMID:21983523 NCBI chr10:109,518,429...109,521,288
Ensembl chr 3:75,643,054...75,644,954
Ensembl chr10:75,643,054...75,644,954
JBrowse link
G Adam9 ADAM metallopeptidase domain 9 decreases expression EXP Yohimbine results in decreased expression of ADAM9 mRNA CTD PMID:21983523 NCBI chr16:71,810,377...71,887,926
Ensembl chr16:71,810,377...71,887,926
JBrowse link
G Adamts4 ADAM metallopeptidase with thrombospondin type 1 motif, 4 increases expression EXP Yohimbine results in increased expression of ADAMTS4 mRNA CTD PMID:21983523 NCBI chr13:89,622,996...89,632,485
Ensembl chr13:89,622,632...89,634,419
JBrowse link
G Adra2a adrenoceptor alpha 2A multiple interactions ISO
EXP
Yohimbine inhibits the reaction [Brimonidine Tartrate promotes the reaction [Phenylephrine binds to and results in increased activity of ADRA2A protein]]; Yohimbine inhibits the reaction [Norepinephrine binds to and results in increased activity of ADRA2A protein]
Yohimbine binds to and results in decreased activity of ADRA2A protein
CTD PMID:8397342 PMID:10742289 PMID:17666864 NCBI chr 1:274,766,283...274,769,083
Ensembl chr 1:274,766,283...274,769,081
JBrowse link
G Adrb1 adrenoceptor beta 1 multiple interactions EXP [Imipramine co-treated with Yohimbine] results in decreased activity of ADRB1 protein CTD PMID:2868116 NCBI chr 1:277,537,585...277,538,985
Ensembl chr 1:277,537,585...277,538,985
JBrowse link
G Avpr1a arginine vasopressin receptor 1A multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of AVPR1A mRNA CTD PMID:28843594 NCBI chr 7:67,341,366...67,345,290
Ensembl chr 7:67,341,080...67,345,308
JBrowse link
G Bhmt betaine-homocysteine S-methyltransferase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of BHMT mRNA CTD PMID:28843594 NCBI chr 2:23,236,573...23,256,158
Ensembl chr 2:23,236,575...23,256,158
JBrowse link
G Calu calumenin increases expression EXP Yohimbine results in increased expression of CALU mRNA CTD PMID:21983523 NCBI chr 4:56,625,611...56,653,112
Ensembl chr 4:56,625,561...56,653,111
JBrowse link
G Cat catalase multiple interactions EXP Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in decreased activity of CAT protein] CTD PMID:27028940 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Ccng1 cyclin G1 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of CCNG1 mRNA CTD PMID:28843594 NCBI chr10:25,903,925...25,910,298
Ensembl chr10:25,903,911...25,910,325
JBrowse link
G Cd36 CD36 molecule multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of CD36 mRNA CTD PMID:28843594 NCBI chr 4:14,150,309...14,191,498
Ensembl chr 4:14,001,761...14,249,749
JBrowse link
G Cdc14b cell division cycle 14B multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of CDC14B mRNA CTD PMID:28843594 NCBI chr17:1,709,703...1,797,732
Ensembl chr17:1,703,943...1,797,750
JBrowse link
G Cemip2 cell migration inducing hyaluronidase 2 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of CEMIP2 mRNA CTD PMID:28843594 NCBI chr 1:239,397,322...239,474,931
Ensembl chr 1:239,398,043...239,474,931
JBrowse link
G Clic1 chloride intracellular channel 1 decreases expression EXP Yohimbine results in decreased expression of CLIC1 mRNA CTD PMID:21983523 NCBI chr20:5,040,314...5,049,166
Ensembl chr20:5,040,337...5,049,166
JBrowse link
G Col2a1 collagen type II alpha 1 chain multiple interactions EXP Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in decreased activity of CAT protein]; Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of PTGS2 protein]; Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of RELA protein]; Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of TNF protein] CTD PMID:27028940 NCBI chr 7:139,454,945...139,484,403
Ensembl chr 7:139,455,242...139,483,997
JBrowse link
G Crh corticotropin releasing hormone multiple interactions EXP Yohimbine affects the reaction [Norepinephrine affects the expression of and affects the secretion of CRH protein]; Yohimbine inhibits the reaction [Nitroprusside results in increased expression of and results in increased secretion of CRH protein] CTD PMID:3497798 NCBI chr 2:104,459,999...104,461,863
Ensembl chr 2:104,459,999...104,461,863
JBrowse link
G Cxcl12 C-X-C motif chemokine ligand 12 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of CXCL12 mRNA CTD PMID:28843594 NCBI chr 4:149,261,044...149,273,891
Ensembl chr 4:149,261,044...149,273,891
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of CYP1A2 mRNA CTD PMID:28843594 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 affects metabolic processing ISO CYP2D6 gene polymorphism affects the metabolism of Yohimbine CTD PMID:15289791 NCBI chr 7:123,599,264...123,608,436
Ensembl chr 7:123,599,266...123,608,436
JBrowse link
G Cyp3a62 cytochrome P450, family 3, subfamily a, polypeptide 62 multiple interactions
affects metabolic processing
ISO Yohimbine analog inhibits the reaction [Calcitriol results in increased expression of CYP3A4 protein]
CYP3A4 gene polymorphism affects the metabolism of Yohimbine
CTD PMID:15289791 PMID:29782822 NCBI chr12:18,679,809...18,709,397
Ensembl chr12:18,678,594...18,709,397
JBrowse link
G Fasn fatty acid synthase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of FASN mRNA CTD PMID:28843594 NCBI chr10:109,987,735...110,005,901
Ensembl chr10:109,987,735...110,005,901
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of GCLC mRNA CTD PMID:28843594 NCBI chr 8:85,059,051...85,097,471
Ensembl chr 8:85,059,051...85,097,468
JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of GSR mRNA CTD PMID:28843594 NCBI chr16:62,197,617...62,239,987
Ensembl chr16:62,197,617...62,241,361
JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A multiple interactions ISO [Yohimbine co-treated with Cocaine] affects the reaction [HTR2A protein results in increased susceptibility to 4-iodo-2,5-dimethoxyphenylisopropylamine] CTD PMID:8392199 NCBI chr15:56,666,152...56,732,469
Ensembl chr15:56,666,012...56,735,382
JBrowse link
G Lpl lipoprotein lipase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of LPL mRNA CTD PMID:28843594 NCBI chr16:22,537,687...22,561,487
Ensembl chr16:22,537,056...22,561,496
JBrowse link
G Lss lanosterol synthase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] affects the expression of LSS mRNA CTD PMID:28843594 NCBI chr20:12,844,522...12,870,474
Ensembl chr20:12,842,884...12,870,497
JBrowse link
G Maoa monoamine oxidase A decreases activity ISO Yohimbine results in decreased activity of MAOA protein CTD PMID:28302559 NCBI chr  X:6,554,698...6,620,722
Ensembl chr  X:6,554,698...6,620,722
JBrowse link
G Mir101a microRNA 101a multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of MIR101A mRNA CTD PMID:28843594 NCBI chr 5:120,168,437...120,168,511
Ensembl chr 5:120,168,433...120,168,515
JBrowse link
G Mir122 microRNA 122 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] affects the expression of MIR122 mRNA CTD PMID:28843594 NCBI chr18:60,755,285...60,755,369 JBrowse link
G Mir192 microRNA 192 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of MIR192 mRNA CTD PMID:28843594 NCBI chr 1:221,634,971...221,635,080
Ensembl chr 1:221,634,971...221,635,080
JBrowse link
G Mlxipl MLX interacting protein-like multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of MLXIPL mRNA CTD PMID:28843594 NCBI chr12:24,590,645...24,619,639 JBrowse link
G Myct1 myc target 1 increases expression EXP Yohimbine results in increased expression of MYCT1 mRNA CTD PMID:21983523 NCBI chr 1:42,121,572...42,132,131
Ensembl chr 1:42,121,636...42,131,547
JBrowse link
G Nfkbiz NFKB inhibitor zeta increases expression EXP Yohimbine results in increased expression of NFKBIZ mRNA CTD PMID:21983523 NCBI chr11:47,243,342...47,271,487
Ensembl chr11:47,243,342...47,271,487
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions EXP Yohimbine inhibits the reaction [endotoxin, Escherichia coli results in increased expression of NOS2 protein]; Yohimbine inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:17637181 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Npy neuropeptide Y multiple interactions EXP Yohimbine inhibits the reaction [Clonidine results in decreased expression of NPY mRNA] CTD PMID:1878751 NCBI chr 4:79,557,856...79,565,059
Ensembl chr 4:79,557,854...79,565,097
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of NQO1 mRNA CTD PMID:28843594 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Nrip3 nuclear receptor interacting protein 3 increases expression EXP Yohimbine results in increased expression of NRIP3 mRNA CTD PMID:21983523 NCBI chr 1:174,385,424...174,411,141
Ensembl chr 1:174,385,424...174,411,141
JBrowse link
G Pla2g12a phospholipase A2, group XIIA multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of PLA2G12A mRNA CTD PMID:28843594 NCBI chr 2:235,311,664...235,327,972
Ensembl chr 2:235,311,719...235,327,972
JBrowse link
G Prl prolactin increases expression ISO Yohimbine results in increased expression of PRL protein CTD PMID:3153710 NCBI chr17:39,814,236...39,824,299
Ensembl chr17:39,814,244...39,824,299
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of PTGS2 protein]; Yohimbine inhibits the reaction [endotoxin, Escherichia coli results in increased expression of PTGS2 protein]; Yohimbine inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein] CTD PMID:17637181 PMID:27028940 NCBI chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of RELA protein] CTD PMID:27028940 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G Ren renin multiple interactions
increases expression
EXP Chlorisondamine inhibits the reaction [Yohimbine results in increased expression of REN protein]; Indomethacin inhibits the reaction [Yohimbine results in increased expression of REN protein]; Meclofenamic Acid inhibits the reaction [Yohimbine results in increased expression of REN protein]; Propranolol inhibits the reaction [Yohimbine results in increased expression of REN protein] CTD PMID:6323192 NCBI chr13:50,502,724...50,513,953
Ensembl chr13:50,502,724...50,514,151
JBrowse link
G Scd stearoyl-CoA desaturase multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of SCD1 mRNA CTD PMID:28843594 NCBI chr 1:264,159,966...264,173,061
Ensembl chr 1:264,160,129...264,172,729
JBrowse link
G Thrsp thyroid hormone responsive multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in decreased expression of THRSP mRNA CTD PMID:28843594 NCBI chr 1:162,381,251...162,385,575
Ensembl chr 1:162,381,253...162,385,575
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP Yohimbine inhibits the reaction [[COL2A1 protein co-treated with Adjuvants, Immunologic co-treated with Freund's Adjuvant] results in increased expression of TNF protein] CTD PMID:27028940 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Txnrd1 thioredoxin reductase 1 multiple interactions ISO [Caffeine co-treated with coclaurine co-treated with aegeline co-treated with higenamine co-treated with Yohimbine co-treated with Hydrolyzable Tannins] results in increased expression of TXNRD1 mRNA CTD PMID:28843594 NCBI chr 7:26,946,124...26,984,400
Ensembl chr 7:26,946,125...26,984,400
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19875
    role 19825
      biological role 19825
        pharmacological role 18870
          antagonist 16306
            dopamine receptor D2 antagonist 53
              yohimbine 50
Path 2
Term Annotations click to browse term
  CHEBI ontology 19875
    subatomic particle 19873
      composite particle 19873
        hadron 19873
          baryon 19873
            nucleon 19873
              atomic nucleus 19873
                atom 19873
                  main group element atom 19763
                    p-block element atom 19763
                      carbon group element atom 19668
                        carbon atom 19657
                          organic molecular entity 19657
                            organic group 18569
                              cyclic organic group 1849
                                organic heterobicyclic ring 1849
                                  indole skeleton 1849
                                    indole alkaloid 1849
                                      terpenoid indole alkaloid 1467
                                        monoterpenoid indole alkaloid 1458
                                          yohimban alkaloid 158
                                            yohimban 51
                                              17-yohimbol 50
                                                17alpha-yohimbol 50
                                                  yohimbic acid 50
                                                    yohimbine 50
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