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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 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
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 4:25,150,998...25,209,489
Ensembl chr 4:25,151,953...25,209,202
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 1:242,664,657...242,723,239
Ensembl chr 1:242,664,657...242,723,238
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 chr10:79,296,681...79,342,749
Ensembl chr10:79,296,693...79,342,595
JBrowse link
G Actg1 actin, gamma 1 increases expression EXP Yohimbine results in increased expression of ACTG1 mRNA CTD PMID:21983523 NCBI chr10:105,619,738...105,622,587
Ensembl chr10:105,619,737...105,624,232
JBrowse link
G Adam9 ADAM metallopeptidase domain 9 decreases expression EXP Yohimbine results in decreased expression of ADAM9 mRNA CTD PMID:21983523 NCBI chr16:67,022,538...67,101,647
Ensembl chr16:67,022,655...67,100,917
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 chr13:83,670,556...83,680,045
Ensembl chr13:83,670,183...83,680,065
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 1:253,061,480...253,064,280
Ensembl chr 1:253,060,218...253,064,365
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 1:255,772,217...255,773,617
Ensembl chr 1:255,771,597...255,807,259
JBrowse link
G Aldoc aldolase, fructose-bisphosphate C 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 ALDOA mRNA CTD PMID:28843594 NCBI chr10:63,217,477...63,221,066
Ensembl chr10:63,217,451...63,221,066
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 7:58,114,306...58,118,230
Ensembl chr 7:58,114,284...58,122,215
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 2:24,859,871...24,879,449
Ensembl chr 2:24,859,873...24,879,742
JBrowse link
G Calu calumenin increases expression EXP Yohimbine results in increased expression of CALU mRNA CTD PMID:21983523 NCBI chr 4:57,949,086...57,976,589
Ensembl chr 4:57,948,997...57,976,593
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 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
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 chr10:25,176,231...25,182,604
Ensembl chr10:25,176,234...25,181,641
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 4:17,317,343...17,410,084
Ensembl chr 4:17,354,466...17,513,903
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 chr17:844,731...934,787
Ensembl chr17:844,685...933,235
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 1:219,330,295...219,407,760
Ensembl chr 1:219,337,985...219,407,760
JBrowse link
G Clic1 chloride intracellular channel 1 decreases expression EXP Yohimbine results in decreased expression of CLIC1 mRNA CTD PMID:21983523 NCBI chr20:3,764,867...3,773,711
Ensembl chr20:3,761,461...3,773,712
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 7:129,098,489...129,127,620
Ensembl chr 7:129,098,786...129,127,546
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 2:102,143,055...102,144,919
Ensembl chr 2:102,143,055...102,144,919
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 4:150,388,326...150,401,173
Ensembl chr 4:150,388,325...150,401,168
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 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 affects metabolic processing
affects response to substance
ISO CYP2D6 gene polymorphism affects the metabolism of Yohimbine
CYP2D6 protein affects the susceptibility to Yohimbine
CTD PMID:15289791 PMID:34027562 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 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 chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
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 chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261
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 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
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 chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
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 chr15:49,950,035...50,022,188
Ensembl chr15:49,950,804...50,020,928
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 chr16:20,830,055...20,853,855
Ensembl chr16:20,829,465...20,855,249
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 chr20:12,091,138...12,118,858
Ensembl chr20:12,092,774...12,118,762
JBrowse link
G Maoa monoamine oxidase A decreases activity ISO Yohimbine results in decreased activity of MAOA protein CTD PMID:28302559 NCBI chr  X:6,032,172...6,098,308
Ensembl chr  X:6,030,795...6,099,593
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 5:115,966,332...115,966,406
Ensembl chr 5:115,966,328...115,966,410
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 chr18:58,758,703...58,758,787 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 1:203,564,946...203,565,055
Ensembl chr 1:203,564,946...203,565,055
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 chr12:21,542,964...21,577,120
Ensembl chr12:21,543,576...21,577,112
JBrowse link
G Myct1 myc target 1 increases expression EXP Yohimbine results in increased expression of MYCT1 mRNA CTD PMID:21983523 NCBI chr 1:42,018,137...42,029,410
Ensembl chr 1:42,018,137...42,029,410
JBrowse link
G Nfkbiz NFKB inhibitor zeta increases expression EXP Yohimbine results in increased expression of NFKBIZ mRNA CTD PMID:21983523 NCBI chr11:44,782,676...44,810,723
Ensembl chr11:44,782,676...44,810,723
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 chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
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 4:78,881,294...78,888,495
Ensembl chr 4:78,881,264...78,888,495
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 1:163,789,738...163,815,036
Ensembl chr 1:163,789,738...163,815,600
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 2:218,436,450...218,452,760
Ensembl chr 2:218,436,513...218,452,740
JBrowse link
G Prl prolactin increases expression ISO Yohimbine results in increased expression of PRL protein CTD PMID:3153710 NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062
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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
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 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
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 chr13:44,796,260...44,807,491
Ensembl chr13:44,796,091...44,807,489
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 1:243,269,745...243,282,878
Ensembl chr 1:243,269,747...243,282,562
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 1:151,723,415...151,727,740
Ensembl chr 1:151,723,086...151,728,075
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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 7:20,830,042...20,914,990
Ensembl chr 7:20,830,045...20,907,863
JBrowse link

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  CHEBI ontology 20072
    role 20024
      biological role 20023
        pharmacological role 19105
          antagonist 16745
            dopamine receptor D2 antagonist 54
              yohimbine 51
Path 2
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  CHEBI ontology 20072
    subatomic particle 20071
      composite particle 20071
        hadron 20071
          baryon 20071
            nucleon 20071
              atomic nucleus 20071
                atom 20071
                  main group element atom 19971
                    p-block element atom 19971
                      carbon group element atom 19894
                        carbon atom 19887
                          organic molecular entity 19887
                            organic group 18965
                              cyclic organic group 1882
                                organic heterobicyclic ring 1882
                                  indole skeleton 1882
                                    indole alkaloid 1882
                                      terpenoid indole alkaloid 1479
                                        monoterpenoid indole alkaloid 1468
                                          yohimban alkaloid 159
                                            yohimban 52
                                              17-yohimbol 51
                                                17alpha-yohimbol 51
                                                  yohimbic acid 51
                                                    yohimbine 51
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