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Troleandomycin

CAT: 0804-HY-108881-03Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-108881-03Size:10 mM - 1 mL
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Description
Troleandomycin (Triacetyloleandomycin), a macrolide acrolide antibiotic, is a selective CYP3A inhibitor. Troleandomycin is an oral corticosteroid for asthma study[1][2][3].
CAS Number
2751-09-9
Product Name Alternative
Triacetyloleandomycin
UNSPSC
12352005
Hazard Statement
H302, H312, H332
Target
Antibiotic; Bacterial; Cytochrome P450
Type
Reference compound
Related Pathways
Anti-infection; Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/troleandomycin.html
Purity
98.58
Solubility
DMSO : 83.33 mg/mL (ultrasonic)
Smiles
O=C1[C@@]2(C[C@@H]([C@@H]([C@H]([C@@H]([C@@H](C)C(O[C@H](C)[C@H](C)[C@@](OC(C)=O)([H])[C@H]1C)=O)O[C@@]3([H])C[C@@H]([C@@H](OC(C)=O)[C@H](C)O3)OC)C)O[C@@]4([H])[C@@H]([C@H](C[C@@H](C)O4)N(C)C)OC(C)=O)C)CO2
Molecular Formula
C41H67NO15
Molecular Weight
813.97
Precautions
H302, H312, H332
References & Citations
[1]Shingen Misaka, et al. Green tea extract affects the cytochrome P450 3A activity and pharmacokinetics of simvastatin in rats. Drug Metab Pharmacokinet. 2013;28 (6) :514-8.|[2]A Honda, et al. Side chain hydroxylations in bile acid biosynthesis catalyzed by CYP3A are markedly up-regulated in Cyp27-/- mice but not in cerebrotendinous xanthomatosis. J Biol Chem. 2001 Sep 14;276 (37) :34579-85.|[3]D J Evans, et al. Troleandomycin as an oral corticosteroid steroid sparing agent in stable asthma. Cochrane Database Syst Rev. 2001; (2) :CD002987.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
CYP3; Macrolide

Chemical Information

Troleandomycin

Troleandomycin is a semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug. It has a role as a xenobiotic and an EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor. It is a macrolide antibiotic, a polyketide, an epoxide, an acetate ester, a monosaccharide derivative and a semisynthetic derivative. It is functionally related to an oleandomycin.

CAS Number2751-09-9
PubChem CID202225
IUPAC Name[(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate
Molecular FormulaC41H67NO15
Molecular Weight814.0
XLogP4.3
Topological Polar Surface Area184
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count16
Rotatable Bond Count12
Heavy Atom Count57
Formal Charge0
Complexity1430
SMILES
C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
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
InChIKey
LQCLVBQBTUVCEQ-QTFUVMRISA-N
Chemical Structure
2D Structure
2D structure of Troleandomycin
CAS: 2751-09-9
CID: 202225
Formula: C41H67NO15
MW: 814.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight814.0
XLogP34.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count16
Rotatable Bond Count12
Exact Mass813.45107043
Monoisotopic Mass813.45107043
Topological Polar Surface Area184 Ų
Heavy Atom Count57
Formal Charge0
Complexity1430
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
ENZ-CHM489-0025Troleandomycin
TBI2227-5MGTroleandomycin, Macrolide antibiotic, Inhibits cytochrome P450

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