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V900930

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C51H79NO13
CAS Number:
53123-88-9
Molecular Weight:
914.17
MDL number:
MFCD00867594
UNSPSC Code:
12352200
PubChem Substance ID:
329830232

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)

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General description

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

Application

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

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

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351,H361fd

Hazard Classifications

Carc. 2 - Repr. 2

WGK

WGK 2

Regulatory Information

涉药品监管产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Targets for cell cycle arrest by the immunosuppressant rapamycin in yeast.
Heitman J, et al.
Science, 253(5022), 905-909 (1991)
Rapamycin (AY-22, 989), a new antifungal antibiotic.
Vezina C, et al.
The Journal of Antibiotics, 28(10), 721-726 (1975)
Efficacy of an autophagy-targeted DNA vaccine against avian leukosis virus subgroup J
Dai Z, et al.
Vaccine, 35(5), 808-813 (2017)
Shutian Zhang et al.
Journal of neuroinflammation, 17(1), 15-15 (2020-01-12)
Microglial mediated neuroinflammation in the rostral ventrolateral medulla (RVLM) plays roles in the etiology of stress-induced hypertension (SIH). It was reported that autophagy influenced inflammation via immunophenotypic switching of microglia. High-mobility group box 1 (HMGB1) acts as a regulator of
Umberto Benedetto et al.
The Journal of thoracic and cardiovascular surgery, 148(4), 1316-1322 (2014-02-14)
Minimally invasive direct coronary artery bypass (MIDCAB) has been proposed to reduce surgical morbidity and improve long-term outcomes compared with stenting in the treatment of isolated proximal left anterior descending artery. However, the survival benefit from MIDCAB still needs to
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