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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:helenalin
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Accession:CHEBI:5635 term browser browse the term
Definition:A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).
Synonyms:exact_synonym: (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
 related_synonym: (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione;   6alpha,8beta-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone;   Formula=C15H18O4;   Helenalin A;   InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1;   InChIKey=ZVLOPMNVFLSSAA-XEPQRQSNSA-N;   SMILES=C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@@]2(C)[C@H]1C=CC2=O
 xref: CAS:6754-13-8;   KEGG:C09473;   KNApSAcK:C00003298
 xref_mesh: MESH:C001329
 xref: PMID:20175984;   PMID:21669190;   PMID:22784363;   PMID:23123298;   PMID:23727063;   PMID:24044884;   Reaxys:28081



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helenalin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Atf4 activating transcription factor 4 increases expression ISO helenalin results in increased expression of ATF4 protein CTD PMID:23123298 NCBI chr 7:111,804,135...111,806,457
Ensembl chr 7:111,804,183...111,806,446
JBrowse link
G Casp3 caspase 3 multiple interactions ISO helenalin inhibits the reaction [CD 437 results in increased activity of CASP3 protein] CTD PMID:16024638 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 multiple interactions ISO helenalin inhibits the reaction [CD 437 results in increased activity of CASP8 protein] CTD PMID:16024638 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Ccl5 C-C motif chemokine ligand 5 multiple interactions ISO helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CCL5 mRNA] CTD PMID:23688403 NCBI chr10:68,322,826...68,327,380
Ensembl chr10:68,322,829...68,327,377
JBrowse link
G Cd40 CD40 molecule multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased expression of CD40 protein]; helenalin inhibits the reaction [Polysaccharides results in increased expression of CD40 protein] CTD PMID:15894585 NCBI chr 3:153,790,372...153,805,279
Ensembl chr 3:153,790,449...153,805,534
JBrowse link
G Cd80 Cd80 molecule multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased expression of CD80 protein]; helenalin inhibits the reaction [Polysaccharides results in increased expression of CD80 protein] CTD PMID:15894585 NCBI chr11:62,254,543...62,293,414
Ensembl chr11:62,254,624...62,292,030
JBrowse link
G Cd83 CD83 molecule multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased expression of CD83 protein]; helenalin inhibits the reaction [Polysaccharides results in increased expression of CD83 protein] CTD PMID:15894585 NCBI chr17:20,887,309...20,907,009
Ensembl chr17:20,887,309...20,907,083
JBrowse link
G Cd86 CD86 molecule multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased expression of CD86 protein]; helenalin inhibits the reaction [Polysaccharides results in increased expression of CD86 protein] CTD PMID:15894585 NCBI chr11:64,142,193...64,200,816
Ensembl chr11:64,163,828...64,200,818
JBrowse link
G Chuk component of inhibitor of nuclear factor kappa B kinase complex multiple interactions ISO helenalin inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of CHUK protein] CTD PMID:21048310 NCBI chr 1:242,959,539...242,995,066
Ensembl chr 1:242,959,760...242,995,065
JBrowse link
G Cyp2a1 cytochrome P450, family 2, subfamily a, polypeptide 1 increases oxidation
decreases activity
ISO CYP2A13 protein results in increased oxidation of helenalin
helenalin results in decreased activity of CYP2A13 protein
CTD PMID:34989853 NCBI chr 1:82,231,611...82,244,887
Ensembl chr 1:82,231,611...82,244,887
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 increases oxidation ISO CYP2B6 protein results in increased oxidation of helenalin CTD PMID:34989853 NCBI chr 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases activity
increases oxidation
ISO helenalin results in decreased activity of CYP3A4 protein
CYP3A4 protein results in increased oxidation of helenalin
CTD PMID:34989853 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 decreases activity
increases oxidation
ISO helenalin results in decreased activity of CYP3A5 protein
CYP3A5 protein results in increased oxidation of helenalin
CTD PMID:34989853 NCBI chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO helenalin results in increased expression of DDIT3 protein CTD PMID:23123298 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Ddit4 DNA-damage-inducible transcript 4 increases expression ISO helenalin results in increased expression of DDIT4 protein CTD PMID:23123298 NCBI chr20:27,891,989...27,894,088
Ensembl chr20:27,891,998...27,894,105
JBrowse link
G Icam1 intercellular adhesion molecule 1 multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased expression of ICAM1 protein]; helenalin inhibits the reaction [Polysaccharides results in increased expression of ICAM1 protein]
helenalin inhibits the reaction [TNF protein results in increased expression of ICAM1 mRNA]; helenalin inhibits the reaction [TNF protein results in increased expression of ICAM1 protein]
CTD PMID:15894585 PMID:19608869 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438
JBrowse link
G Il10 interleukin 10 multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased secretion of IL10 protein]; helenalin inhibits the reaction [Polysaccharides results in increased secretion of IL10 protein] CTD PMID:15894585 NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313
JBrowse link
G Il12a interleukin 12A multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased secretion of [IL12A protein binds to IL12B protein]]; helenalin inhibits the reaction [Polysaccharides results in increased secretion of [IL12A protein binds to IL12B protein]] CTD PMID:15894585 NCBI chr 2:152,965,769...152,973,035
Ensembl chr 2:152,965,769...152,972,734
JBrowse link
G Il12b interleukin 12B multiple interactions ISO helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased secretion of [IL12A protein binds to IL12B protein]]; helenalin inhibits the reaction [Drugs, Chinese Herbal results in increased secretion of IL12B protein]; helenalin inhibits the reaction [Polysaccharides results in increased secretion of [IL12A protein binds to IL12B protein]]; helenalin inhibits the reaction [Polysaccharides results in increased secretion of IL12B protein] CTD PMID:15894585 NCBI chr10:28,888,832...28,903,802
Ensembl chr10:28,893,008...28,902,903
JBrowse link
G Il4 interleukin 4 multiple interactions ISO helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CCL5 mRNA]; helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CXCL8 mRNA]; helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]; helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein] CTD PMID:23688403 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
JBrowse link
G Il6 interleukin 6 multiple interactions ISO helenalin inhibits the reaction [Lipopolysaccharides results in increased secretion of IL6 protein] CTD PMID:17532054 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Irak1 interleukin-1 receptor-associated kinase 1 multiple interactions ISO helenalin inhibits the reaction [Lipopolysaccharides results in increased degradation of IRAK1 protein] CTD PMID:16678799 NCBI chr  X:151,768,621...151,778,521
Ensembl chr  X:151,768,777...151,778,521
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO helenalin inhibits the reaction [CD 437 results in decreased expression of NFKBIA protein]
helenalin inhibits the reaction [Lipopolysaccharides results in increased phosphorylation of NFKBIA protein]
CTD PMID:16024638 PMID:21048310 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO helenalin inhibits the reaction [Lipopolysaccharides results in increased expression of NOS2 protein] CTD PMID:21048310 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO helenalin inhibits the reaction [Particulate Matter results in increased expression of PTGS2 mRNA]; helenalin inhibits the reaction [Particulate Matter results in increased expression of PTGS2 protein]
helenalin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 protein]
CTD PMID:21048310 PMID:28495310 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions
decreases activity
ISO helenalin inhibits the reaction [Acetylmuramyl-Alanyl-Isoglutamine results in increased activity of RELA protein]; helenalin inhibits the reaction [CD 437 results in increased localization of RELA protein]; helenalin inhibits the reaction [Particulate Matter results in increased phosphorylation of RELA protein]
helenalin results in decreased activity of RELA protein
helenalin inhibits the reaction [TNF protein results in increased phosphorylation of RELA protein]
CTD PMID:15930313 PMID:16024638 PMID:18413660 PMID:19608869 PMID:28495310 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
JBrowse link
G Sod2 superoxide dismutase 2 multiple interactions ISO helenalin inhibits the reaction [N-(2-mercaptoethyl)-1,3-diaminopropane results in increased expression of SOD2 protein] CTD PMID:16540396 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189
JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions ISO helenalin inhibits the reaction [Lipopolysaccharides promotes the reaction [TLR4 protein binds to TLR4 protein]] CTD PMID:16678799 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 multiple interactions ISO helenalin inhibits the reaction [TNF protein results in increased expression of ICAM1 mRNA]; helenalin inhibits the reaction [TNF protein results in increased expression of ICAM1 protein]; helenalin inhibits the reaction [TNF protein results in increased expression of VCAM1 mRNA]; helenalin inhibits the reaction [TNF protein results in increased expression of VCAM1 protein]; helenalin inhibits the reaction [TNF protein results in increased phosphorylation of RELA protein] CTD PMID:19608869 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Tnfrsf10b TNF receptor superfamily member 10b multiple interactions ISO helenalin inhibits the reaction [CD 437 results in increased expression of TNFRSF10A protein] CTD PMID:16024638 NCBI chr15:44,840,386...44,868,318
Ensembl chr15:44,840,386...44,867,467
JBrowse link
G Tslp thymic stromal lymphopoietin multiple interactions ISO helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]; helenalin inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein] CTD PMID:23688403 NCBI chr18:24,447,409...24,454,244
Ensembl chr18:24,449,844...24,453,548
JBrowse link
G Vcam1 vascular cell adhesion molecule 1 multiple interactions ISO helenalin inhibits the reaction [TNF protein results in increased expression of VCAM1 mRNA]; helenalin inhibits the reaction [TNF protein results in increased expression of VCAM1 protein] CTD PMID:19608869 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 19918
    role 19894
      application 19729
        anti-inflammatory agent 16531
          helenalin 32
Path 2
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  CHEBI ontology 19918
    subatomic particle 19916
      composite particle 19916
        hadron 19916
          baryon 19916
            nucleon 19916
              atomic nucleus 19916
                atom 19916
                  main group element atom 19866
                    p-block element atom 19866
                      carbon group element atom 19811
                        carbon atom 19806
                          organic molecular entity 19806
                            organic group 18995
                              organic divalent group 18969
                                organodiyl group 18969
                                  carbonyl group 18922
                                    carbonyl compound 18922
                                      carboxylic ester 16506
                                        lactone 12533
                                          terpene lactone 2176
                                            sesquiterpene lactone 2030
                                              helenalin 32
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