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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 4:26,312,403...26,488,456
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 4:26,106,895...26,164,440
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 1:252,613,875...252,672,459
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 chr10:79,793,571...79,839,528
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 chr10:106,118,106...106,120,951
Ensembl chr10:105,619,737...105,624,232
Ensembl chr 3:105,619,737...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 chr16:73,725,186...73,804,284
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 chr13:86,203,011...86,212,500
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 1:263,066,780...263,069,580
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 1:265,777,103...265,780,114
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 chr10:63,715,544...63,719,133
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 7:59,999,743...60,003,667
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 2:26,594,852...26,614,429
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 4:58,914,456...58,941,957
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 3:110,297,340...110,329,526
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 chr10:25,678,503...25,684,876
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 4:18,209,088...18,302,142
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 chr17:850,272...938,972
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 1:228,756,826...228,834,313
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 chr20:3,769,522...3,778,367
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 7:130,977,561...131,006,627
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 2:104,059,184...104,061,048
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 4:152,060,781...152,073,628
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 8:66,971,261...66,978,149
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 7:115,762,662...115,771,832
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 chr12:14,321,771...14,343,886
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 chr10:106,570,415...106,588,581
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 8:87,510,251...87,548,896
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 chr16:65,185,574...65,228,742
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 chr15:56,360,647...56,428,703
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 chr16:25,596,205...25,621,928
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 chr20:12,090,641...12,118,230
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:8,615,239...8,681,372
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 5:121,081,683...121,081,757
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 chr18:61,028,817...61,028,901 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 1:212,994,209...212,994,318
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 chr12:27,178,158...27,213,675
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 chr11:58,251,720...58,279,767
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 chr10:64,313,335...64,349,221
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 4:80,212,111...80,219,310
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 chr19:52,205,374...52,220,267
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 1:173,224,532...173,249,829
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 2:221,110,722...221,126,966
Ensembl chr 2:218,436,513...218,452,740
JBrowse link
G Pomc proopiomelanocortin multiple interactions EXP Yohimbine inhibits the reaction [Ethanol results in increased secretion of POMC protein] CTD PMID:22236039 NCBI chr 6:32,659,137...32,665,175
Ensembl chr 6:26,939,837...26,945,664
JBrowse link
G Prl prolactin increases expression ISO Yohimbine results in increased expression of PRL protein CTD PMID:3153710 NCBI chr17:38,287,355...38,298,234
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 chr13:64,714,063...64,722,320
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 1:212,354,336...212,364,815
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 chr13:47,348,312...47,359,539
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 1:253,218,968...253,232,101
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 1:161,134,640...161,138,964
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 chr20:3,626,685...3,629,303
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 7:22,717,620...22,802,553
Ensembl chr 7:20,830,045...20,907,863
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19899
    role 19870
      biological role 19868
        pharmacological role 19105
          antagonist 17268
            dopamine receptor D2 antagonist 55
              yohimbine 52
Path 2
Term Annotations click to browse term
  CHEBI ontology 19899
    subatomic particle 19897
      composite particle 19897
        hadron 19897
          baryon 19897
            nucleon 19897
              atomic nucleus 19897
                atom 19897
                  main group element atom 19836
                    p-block element atom 19836
                      carbon group element atom 19776
                        carbon atom 19772
                          organic molecular entity 19772
                            heteroorganic entity 19537
                              organonitrogen compound 18854
                                alkaloid 8035
                                  indole alkaloid 1994
                                    terpenoid indole alkaloid 1502
                                      monoterpenoid indole alkaloid 1484
                                        yohimban alkaloid 160
                                          yohimban 53
                                            17-yohimbol 52
                                              17alpha-yohimbol 52
                                                yohimbic acid 52
                                                  yohimbine 52
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