CLARITHROMYCIN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J01FA09
UNII H1250JIK0A
EPA CompTox DTXSID3022829

Structure

InChI Key AGOYDEPGAOXOCK-KCBOHYOISA-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](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
InChI
InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C38H69NO13
Molecular Weight 747.96
AlogP 2.44
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 8.0
Polar Surface Area 182.91
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 52.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Bacterial 70S ribosome inhibitor INHIBITOR PubMed PubMed DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 5490 -
Ion channel Ligand-gated ion channel GABA-A receptor
- - 1 - 18-45
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 33113-58884 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 3090 - - 54-81
Assay Description Organism Bioactivity Reference
Cell free inhibiting activity against Streptococcus pneumoniae 5635(Wild type ribosomes for transcription/translation assay) Streptococcus pneumoniae 90.0 nM
Inhibition of growth of Mycobacterium avium (ATCC 25291) was determined using microplate alamar blue assay at 2 ug/mL concentration with compound dissolved in DMSO Mycobacterium avium 95.0 %
Antimycobacterial activity against Mycobacterium avium ATCC 25291 at 2 ug/mL by microplate Alamar blue assay Mycobacterium avium 95.0 %
Antimycobacterial activity against Mycobacterium avium ATCC 25291 at 2 ug/mL after 24 to 48 hrs by MABA Mycobacterium avium 95.0 %
Antimycobacterial activity against Mycobacterium avium ATCC 25291 at 2 uM by microplate alamar blue assay Mycobacterium avium 95.0 %
Inhibition of Helicobacter pylori invasion into human AGS cells at 2.5 uM after 6 hrs Helicobacter pylori 90.0 %
Inhibition of Helicobacter pylori-induced inflammation in human AGS cells assessed as reduction of IL-8 production at 10 uM by ELISA Helicobacter pylori 81.9 %
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1900 (Counter Screen), 1677 (Project Summary), 1902 (Retest at Dose), 1662 (Primary HTS)] Streptococcus 60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus 60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus pyogenes M1 GAS 60.0 nM
Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 assessed as decrease of CFU after 24 hrs Staphylococcus aureus 0.8 ug.mL-1
Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 infected in human THP1 cells assessed as decrease of CFU after 24 hrs Staphylococcus aureus 0.046 ug.mL-1
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 73.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 53.8 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 5.1 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 56.72 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 80.47 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -1.12 %
Negative allosteric modulation of GABA-A receptor (unknown origin) at 3 uM by whole cell patch clamp assay Homo sapiens 18.0 %
Negative allosteric modulation of GABA-A receptor (unknown origin) at 300 uM by whole cell patch clamp assay Homo sapiens 45.0 %
Displacement of [3H]FMZ from GABA-A receptor in rat brain assessed as Kd of [3H]-FMZ at 10 uM after 30 mins by autoradiography (Rvb = 0.66 +/- 0.12 nM) Rattus norvegicus 0.64 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -3.046 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 %

Related Entries

Environmental Exposure

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Cross References

Resources Reference
ChEBI 3732
ChEMBL CHEMBL1741
DrugBank DB01211
DrugCentral 668
FDA SRS H1250JIK0A
Human Metabolome Database HMDB0015342
Guide to Pharmacology 10903
KEGG C06912
PDB CTY
PharmGKB PA449028
PubChem 84029
SureChEMBL SCHEMBL38125
ZINC ZINC000085534098
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