(1R,9S,12S,15R,16Z,18R,19R,21R,23S,24Z,26Z,28Z,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

• ChemBase ID: 132924
• Molecular Formular: C51H79NO13
• Molecular Mass: 914.17186
• Monoisotopic Mass: 913.55514159
• SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C\C=C/C=C\[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C\[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]1CC[C@H]([C@@H](C1)OC)O)C)/C)O)OC)C)C)/C)OC
• Canonical SMILES: CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@H]([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H](CC[C@H]2C)C[C@H](OC)/C(=C\C=C/C=C\[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C\[C@H](C(=O)C1)C)/C)O)OC)C)C)/C)C
• InChI: 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
• InChIKey: QFJCIRLUMZQUOT-BLBZBZKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,15R,16Z,18R,19R,21R,23S,24Z,26Z,28Z,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• IUPAC Traditional name: (1R,9S,12S,15R,16Z,18R,19R,21R,23S,24Z,26Z,28Z,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0^4,^9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
• Synonyms: 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine; AY 22989; Sirolimus; Rapamycin from Streptomyces hygroscopicus

Database IDs

• CAS Number: 53123-88-9
• MDL Number: MFCD00867594
• PubChem SID: 162227201; 24899339
• PubChem CID: 71308609

CALCULATED PROPERTIES

• Acid pKa: 9.963728
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 7.4508247
• LogD (pH = 7.4): 7.4496565
• Log P: 7.45084
• Molar Refractivity: 250.6632 cm^3
• Polarizability: 97.655174 Å^3
• Polar Surface Area: 195.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble2 mM
• Apperance: off-white powder

Safety Information

• RTECS: VE6250000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... FKBP1A(2280)

Product Information

• Purity: ≥95% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - R0395

Frequently Asked Questions
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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.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information