TROLEANDOMYCIN

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Search structure


Trade Names	TAO
Synonyms	Acetyloleandomycin NSC-108166 Oleandomycin (as troleandomycin) Oleandomycin triacetate ester Triacetyloleandomycin Troleandomycin
Status
Molecule Category	UNKNOWN
ATC	J01FA08
UNII	C4DZ64560D


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	LQCLVBQBTUVCEQ-QTFUVMRISA-N
Smiles	CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OC(C)=O)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](OC(C)=O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1OC(C)=O
InChI	InChI=1S/C41H67NO15/c1-19-17-41(18-49-41)38(46)23(5)34(53-27(9)43)21(3)25(7)52-39(47)24(6)35(56-32-16-31(48-14)36(26(8)51-32)54-28(10)44)22(4)33(19)57-40-37(55-29(11)45)30(42(12)13)15-20(2)50-40/h19-26,30-37,40H,15-18H2,1-14H3/t19-,20+,21-,22+,23+,24+,25+,26-,30-,31-,32-,33-,34-,35-,36-,37+,40-,41+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C41H67NO15
Molecular Weight	813.98
AlogP	3.62
Hydrogen Bond Acceptor	16.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	9.0
Polar Surface Area	184.19
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	57.0

Bioactivity

Mechanism of Action	Action	Reference
70S ribosome inhibitor	INHIBITOR	KEGG PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	7998-61000	-	-	-
Enzyme Hydrolase	-	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	41

Assay Description	Organism	Bioactivity	Reference
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	Electrophorus electricus	14.76 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method	Equus caballus	-1.09 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	40.51 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	41.97 %

Related Entries

Cross References

Resources	Reference
ChEBI	45735
ChEMBL	CHEMBL564085
DrugBank	DB13179
DrugCentral	2769
FDA SRS	C4DZ64560D
Human Metabolome Database	HMDB0015448
Guide to Pharmacology	10209
KEGG	C12753
PharmGKB	PA127840611
PubChem	202225
SureChEMBL	SCHEMBL125071
ZINC	ZINC000169307271

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).