ERYTHROMYCIN

Search structure
Trade Names:
Synonyms:
PCE
Status: Approved (1964)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D10AF02
UNII: 63937KV33D

Structure
InChI Key ULGZDMOVFRHVEP-RWJQBGPGSA-N
Smile 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)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
InChI
InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C37H67NO13
Molecular Weight 733.94
AlogP 1.79
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 7.0
Polar Surface Area 193.91
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 51.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.06 - EXP
pKa Dissociation Constant 8.88 - EXP
Henry's Law Constant 5.42E-29 atm-m3/mole EST
Atmospheric OH Rate Constant 4.03E-10 cm3/molecule-sec EST
Melting Point 191 deg C EXP
Water Solubility 1.440 mg/L EST
Vapor Pressure 2.28E-27 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial 70S ribosome inhibitor PubMed DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1B Cytochrome P450 1B1
- 40000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 190-33000 - - 45
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 39-39000 - - 27-90
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Motilin receptor
50-1000 44-71 - 37000 -
Other cytosolic protein
- 170-87000 11-29 - 52
Secreted protein
- - 12000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 46-92
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 14
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 7
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 43000 - - 1
Unclassified protein
- 170-87000 11-29 - 99-101

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Epidermolysis Bullosa 3 D004820 ClinicalTrials
Hematemesis 3 D006396 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Gastrointestinal Hemorrhage 3 D006471 ClinicalTrials
Chlamydia Infections 3 D002690 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Gastroparesis 2 D018589 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Bulimia Nervosa 2 D052018 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Renal Insufficiency 1 D051437 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Erectile Dysfunction 1 D007172 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Salt
Salt
Salt
Salt
Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
10.7
Immune system disorders
10.19
Gastrointestinal disorders
9.86
Injury, poisoning and procedural complications
8.78
Skin and subcutaneous tissue disorders
8.12
Nervous system disorders
7.37
Eye disorders
6.05
Vascular disorders
4.39
Cardiac disorders
4.09
Investigations
3.63
Respiratory, thoracic and mediastinal disorders
3.51
Pregnancy, puerperium and perinatal conditions
3.28
Infections and infestations
3.0
Musculoskeletal and connective tissue disorders
2.95
Psychiatric disorders
2.7

Cross References

Resources Reference
CAS NUMBER 114-07-8
ChEBI 42355
ChEMBL CHEMBL532
DrugBank DB00199
DrugCentral 1048
EPA CompTox DTXSID4022991
FDA SRS 63937KV33D
Guide to Pharmacology 1456
KEGG C01912
PDB ERY
PharmGKB PA449493
PubChem 12560
SureChEMBL SCHEMBL2601
ZINC ZINC000085534336
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