V900930

Rapamycin from Streptomyces hygroscopicus

Vetec^™, reagent grade, ≥95%

• Synonym(s): Rapamycin from Streptomyces hygroscopicus, 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus
• Empirical Formula (Hill Notation): C₅₁H₇₉NO₁₃
• CAS Number: 53123-88-9
• Molecular Weight: 914.17
• MDL number: MFCD00867594
• UNSPSC Code: 12352200
• PubChem Substance ID: 329830232

Properties

• grade: reagent grade
• product line: Vetec^™
• Assay: ≥95%
• storage temp.: −20°C
• SMILES string: CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC
• InChI: 1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
• InChI key: QFJCIRLUMZQUOT-HPLJOQBZSA-N
• Gene Information: human ... FKBP1A(2280)

Description

General description

Rapamycin is an anti-fungal antibiotic isolated from Streptomyces hygroscopicus. This antibiotic is active against all strains of Candida albicans.[1] It blocks the signal transduction pathways required for the activation of T-helper cells.[2]

Application

Rapamycin from Streptomyces hygroscopicus has been used to study the efficacy of an autophagy-targeted DNA vaccine against avian leukosis virus subgroup J.[3]

Biochem/physiol Actions

A macrocyclic triene antibiotic that binds to and inhibits the molecular target of rapamycin (mTOR). It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). Rapamycin is a potent immunosuppressant and has anticancer activity.

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H351,H361fd
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2 - Repr. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2