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
Accession: CHEBI:2955
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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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Acta2
actin alpha 2, smooth muscle
multiple interactions
ISO
Azithromycin inhibits the reaction [Transforming Growth Factor beta1 results in increased expression of ACTA2 protein]
CTD
PMID:36581200
NCBI chr 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
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Aif1
allograft inflammatory factor 1
increases expression
ISO
Azithromycin results in increased expression of AIF1 mRNA
CTD
PMID:37995777
NCBI chr20:3,646,784...3,652,670
Ensembl chr20:3,646,777...3,652,668
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Arg1
arginase 1
increases expression
ISO
Azithromycin results in increased expression of ARG1 protein
CTD
PMID:20231397
NCBI chr 1:20,475,878...20,488,422
Ensembl chr 1:20,475,968...20,488,422
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Arsa
arylsulfatase A
increases activity
EXP
Azithromycin results in increased activity of ARSA protein
CTD
PMID:8830663
NCBI chr 7:120,542,788...120,547,577
Ensembl chr 7:120,543,362...120,548,783
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Casp3
caspase 3
decreases expression
ISO
Azithromycin results in decreased expression of CASP3 mRNA
CTD
PMID:37995777
NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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Ccl2
C-C motif chemokine ligand 2
decreases expression
ISO
Azithromycin results in decreased expression of CCL2 protein
CTD
PMID:20231397
NCBI chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226
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Cdh2
cadherin 2
multiple interactions
ISO
Azithromycin inhibits the reaction [Transforming Growth Factor beta1 results in increased expression of CDH2 protein]
CTD
PMID:36581200
NCBI chr18:7,776,704...7,990,934
Ensembl chr18:7,776,704...7,990,167
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Ctnnb1
catenin beta 1
decreases expression
ISO
Azithromycin results in decreased expression of CTNNB1 mRNA
CTD
PMID:37995777
NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111
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Ctsb
cathepsin B
multiple interactions increases activity
EXP
Cycloheximide inhibits the reaction [Azithromycin results in increased activity of CTSB protein]
CTD
PMID:8830663
NCBI chr15:37,389,636...37,410,508
Ensembl chr15:37,389,629...37,410,500
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Cyp3a2
cytochrome P450, family 3, subfamily a, polypeptide 2
decreases activity multiple interactions
ISO
Azithromycin results in decreased activity of CYP3A4 protein Azithromycin inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]
CTD
PMID:16416302
NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008
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Dlg4
discs large MAGUK scaffold protein 4
decreases expression
ISO
Azithromycin results in decreased expression of DLG4 protein
CTD
PMID:37995777
NCBI chr10:54,740,700...54,769,097
Ensembl chr10:54,739,470...54,767,153
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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 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036
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Gfap
glial fibrillary acidic protein
increases expression
ISO
Azithromycin results in increased expression of GFAP mRNA
CTD
PMID:37995777
NCBI chr10:87,852,891...87,861,631
Ensembl chr10:87,852,890...87,861,589
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Ghsr
growth hormone secretagogue receptor
increases expression
ISO
Azithromycin results in increased expression of GHSR mRNA; Azithromycin results in increased expression of GHSR protein
CTD
PMID:37100089
NCBI chr 2:110,268,489...110,271,865
Ensembl chr 2:110,268,489...110,271,865
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Hexb
hexosaminidase subunit beta
increases activity
EXP
Azithromycin results in increased activity of HEXB protein
CTD
PMID:8830663
NCBI chr 2:28,483,997...28,504,165
Ensembl chr 2:28,484,012...28,504,223
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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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
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Il6
interleukin 6
decreases expression
ISO
Azithromycin results in decreased expression of IL6 protein
CTD
PMID:20231397
NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
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Map2
microtubule-associated protein 2
decreases expression
ISO
Azithromycin results in decreased expression of MAP2 mRNA
CTD
PMID:37995777
NCBI chr 9:67,723,422...67,981,886
Ensembl chr 9:67,723,371...67,979,809
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Mki67
marker of proliferation Ki-67
decreases expression
ISO
Azithromycin results in decreased expression of MKI67 mRNA
CTD
PMID:37995777
NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762
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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 8:4,658,588...4,679,099
Ensembl chr 8:4,658,588...4,679,097
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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 8:4,640,397...4,653,963
Ensembl chr 8:4,640,416...4,653,961
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P2ry12
purinergic receptor P2Y12
decreases expression
ISO
Azithromycin results in decreased expression of P2RY12 mRNA
CTD
PMID:37995777
NCBI chr 2:143,481,468...143,523,340
Ensembl chr 2:143,481,430...143,523,361
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Pla1a
phospholipase A1 member A
increases activity
EXP
Azithromycin results in increased activity of PLA1A protein
CTD
PMID:8830663
NCBI chr11:62,320,112...62,357,779
Ensembl chr11:62,320,493...62,357,779
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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 chr12:11,037,028...11,057,251
Ensembl chr12:11,036,698...11,057,251
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Rack1
receptor for activated C kinase 1
multiple interactions
ISO
Azithromycin inhibits the reaction [Transforming Growth Factor beta1 results in increased expression of RACK1 protein]
CTD
PMID:36581200
NCBI chr10:33,169,415...33,174,896
Ensembl chr10:33,169,169...33,174,975
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Rbfox3
RNA binding fox-1 homolog 3
decreases expression
ISO
Azithromycin results in decreased expression of RBFOX3 protein
CTD
PMID:37995777
NCBI chr10:103,720,355...104,157,277
Ensembl chr10:103,720,636...104,156,935
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S100b
S100 calcium binding protein B
increases expression
ISO
Azithromycin results in increased expression of S100B mRNA
CTD
PMID:37995777
NCBI chr20:12,372,866...12,381,619
Ensembl chr20:12,372,881...12,394,743
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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 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268
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Smad3
SMAD family member 3
multiple interactions
ISO
Azithromycin inhibits the reaction [Transforming Growth Factor beta1 results in increased phosphorylation of SMAD3 protein]
CTD
PMID:36581200
NCBI chr 8:64,126,829...64,236,960
Ensembl chr 8:64,110,039...64,236,960
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Sox2
SRY-box transcription factor 2
decreases expression
ISO
Azithromycin results in decreased expression of SOX2 mRNA; Azithromycin results in decreased expression of SOX2 protein
CTD
PMID:37995777
NCBI chr 2:117,536,929...117,539,340
Ensembl chr 2:117,536,929...117,539,338
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Tnf
tumor necrosis factor
decreases expression
ISO
Azithromycin results in decreased expression of TNF protein
CTD
PMID:20231397
NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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Wnt3
Wnt family member 3
decreases expression
ISO
Azithromycin results in decreased expression of WNT3 mRNA
CTD
PMID:37995777
NCBI chr10:88,680,198...88,724,170
Ensembl chr10:88,680,248...88,724,099
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