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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:azithromycin
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Accession:CHEBI:2955 term browser browse the term
Definition:A macrolide antibiotic useful for the treatment of bacterial infections.
Synonyms:related_synonym: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranoside;   (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one;   Azenil;   Azifast;   Azigram;   Azimakrol;   Azitromin;   Formula=C38H72N2O12;   Hemomycin;   InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1;   InChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N;   SMILES=CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O;   Zithromax;   Zmax;   azithromycine;   azithromycinum;   azitromicina
 alt_id: CHEBI:46596
 xref: Beilstein:5387583;   CAS:83905-01-5;   DrugBank:DB00207;   Drug_Central:276;   HMDB:HMDB0014352;   KEGG:C06838;   KEGG:D07486;   LINCS:LSM-5821
 xref_mesh: MESH:D017963
 xref: PDBeChem:ZIT;   PMID:15143799;   PMID:18253999;   Patent:BE892357;   Patent:US4517359;   Reaxys:5387583;   Reaxys:8820027;   Wikipedia:Azithromycin


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azithromycin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Arg1 arginase 1 increases expression ISO Azithromycin results in increased expression of ARG1 protein CTD PMID:20231397 NCBI chr 1:21,525,421...21,537,872
Ensembl chr 1:21,525,421...21,537,863
JBrowse link
G Arsa arylsulfatase A increases activity EXP Azithromycin results in increased activity of ARSA protein CTD PMID:8830663 NCBI chr 7:130,446,644...130,452,632
Ensembl chr 7:130,446,668...130,451,283
JBrowse link
G Ccl2 C-C motif chemokine ligand 2 decreases expression ISO Azithromycin results in decreased expression of CCL2 protein CTD PMID:20231397 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870
JBrowse link
G Ctsb cathepsin B multiple interactions
increases activity
EXP Cycloheximide inhibits the reaction [Azithromycin results in increased activity of CTSB protein] CTD PMID:8830663 NCBI chr15:46,316,741...46,337,613
Ensembl chr15:46,316,741...46,337,612
JBrowse link
G Cyp3a62 cytochrome P450, family 3, subfamily a, polypeptide 62 multiple interactions
decreases activity
ISO Azithromycin inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]
Azithromycin results in decreased activity of CYP3A4 protein
CTD PMID:16416302 NCBI chr12:18,679,809...18,709,397
Ensembl chr12:18,678,594...18,709,397
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression ISO Azithromycin results in increased expression of FOS mRNA; Azithromycin results in increased expression of FOS protein CTD PMID:32454074 NCBI chr 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Hexb hexosaminidase subunit beta increases activity EXP Azithromycin results in increased activity of HEXB protein CTD PMID:8830663 NCBI chr 2:27,983,925...28,003,260
Ensembl chr 2:27,984,117...28,003,186
JBrowse link
G Il1b interleukin 1 beta decreases expression
multiple interactions
ISO Azithromycin results in decreased expression of IL1B protein
Azithromycin inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B mRNA]; Azithromycin inhibits the reaction [Lipopolysaccharides results in increased expression of IL1B protein]
CTD PMID:18435685 PMID:21195124 NCBI chr 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
JBrowse link
G Il6 interleukin 6 decreases expression ISO Azithromycin results in decreased expression of IL6 protein CTD PMID:20231397 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Mmp1 matrix metallopeptidase 1 increases secretion
decreases secretion
ISO Azithromycin results in increased secretion of MMP1 protein
Azithromycin results in decreased secretion of MMP1 protein
CTD PMID:24890593 NCBI chr 8:5,703,206...5,723,593
Ensembl chr 8:5,703,206...5,723,591
JBrowse link
G Mmp3 matrix metallopeptidase 3 increases secretion
decreases secretion
ISO Azithromycin results in increased secretion of MMP3 protein
Azithromycin results in decreased secretion of MMP3 protein
CTD PMID:24890593 NCBI chr 8:5,676,608...5,698,579
Ensembl chr 8:5,676,665...5,698,579
JBrowse link
G Pla1a phospholipase A1 member A increases activity EXP Azithromycin results in increased activity of PLA1A protein CTD PMID:8830663 NCBI chr11:64,882,024...64,919,714
Ensembl chr11:64,882,288...64,919,579
JBrowse link
G Rac1 Rac family small GTPase 1 multiple interactions ISO Azithromycin inhibits the reaction [Lipopolysaccharides results in increased activity of RAC1 protein] CTD PMID:21417583 NCBI chr12:13,090,316...13,111,841
Ensembl chr12:13,090,172...13,111,873
JBrowse link
G Slc22a2 solute carrier family 22 member 2 multiple interactions ISO Azithromycin inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr 1:48,318,025...48,360,219
Ensembl chr 1:48,317,995...48,360,261
JBrowse link
G Tnf tumor necrosis factor decreases expression ISO Azithromycin results in decreased expression of TNF protein CTD PMID:20231397 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19773
    role 19723
      biological role 19723
        xenobiotic 18396
          azithromycin 15
            azithromycin dihydrate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19773
    subatomic particle 19771
      composite particle 19771
        hadron 19771
          baryon 19771
            nucleon 19771
              atomic nucleus 19771
                atom 19771
                  main group element atom 19665
                    p-block element atom 19665
                      carbon group element atom 19583
                        carbon atom 19573
                          organic molecular entity 19573
                            organic group 18603
                              organic divalent group 18594
                                organodiyl group 18594
                                  carbonyl group 18507
                                    carbonyl compound 18507
                                      carboxylic ester 15494
                                        lactone 9711
                                          macrocyclic lactone 1747
                                            macrolide 1618
                                              macrolide antibiotic 396
                                                azithromycin 15
                                                  azithromycin dihydrate 0
paths to the root