ChemSpider 2D Image | Sirolimus | C51H79NO13

Sirolimus

  • Molecular FormulaC51H79NO13
  • Average mass914.172 Da
  • Monoisotopic mass913.555115 Da
  • ChemSpider ID10482078

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 15 of 15 defined stereocentres

More details:

Featured data source
Natural Product Updates

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-Rapamycin
Sirolimus [INN] [USAN] [Wiki]
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-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-tetraen-2,3,10,14,20-penton
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-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
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-méthoxycyclohexyl]-1-méthyléthyl}-19,30-diméthoxy-15,17,21,23,29,35-hexaméthyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tétraène-2,3,10,14,20-pentone
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2-propanyl}-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-tetraen-2,3,10,14,20-penton [German] [ACD/IUPAC Name]
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2-propanyl}-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 [ACD/IUPAC Name]
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-méthoxycyclohexyl]-2-propanyl}-19,30-diméthoxy-15,17,21,23,29,35-hexaméthyl-11,36-dioxa-4- ;azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tétraène-2,3,10,14,20-pentone [French] [ACD/IUPAC Name]
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2-propanyl}-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
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,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
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AY 22989 [DBID]
WY 090217 [DBID]
AY-22989 [DBID]
nchembio.2007.42-comp2 [DBID]
nchembio.79-comp1 [DBID]
NSC 226080 [DBID]
R0395_SIAL [DBID]
WY-090217 [DBID]
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      Soluble to 100 mM in ethanol and to 50 mM in DMSO Tocris Bioscience 1292
      Soluble to 20 mM in ethanol and to 50 mM in DMSO Tocris Bioscience 1292
  • Miscellaneous

    • Safety:

      L04AA10 Wikidata Q32089

    • Chemical Class:

      A macrolide isolated from <ital>Streptomyces hygroscopicus</ital> consisting of a 29-membered ring containing 4 <stereo>trans</stereo> double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent. ChEBI CHEBI:9168

    • Bio Activity:

      <p>mTOR inhibitor and potent immunosuppressant.</p> <p>Complexes with FKBP12 to bind mTORC1 to inhibit mTOR activity and block subsequent activation of p70 s6 kinase (IC<sub>50</sub> = 50 pM).</p> <p>Induces autophagy and apoptosis.</p> <p>Promotes hPSC differentiation to blood progenitor and mesendoderm cells.</p> <p>Rapamycin can also be used in inducible CRISPR/Cas9 systems to enable inducible gene editing.</p> <p>Active in vivo.</p> Hello Bio [HB2779]
      Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylat ion and activation of p70 S6 kinase. Induces autophagy in yeast and mammalian cell lines. Tocris Bioscience 1292
      Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase. Induces autophagy in yeast and mammalian cell lines. Drives hPSC differentiation to mesendoderm and blood progenitor cells. Tocris Bioscience 1292
      Antifungal and immunosuppressant. Specific inhibitor of mTOR (mammalian target of Rapamycin). Complexes with FKBP-12 and binds mTOR inhibiting its activity. Inhibits interleukin-2-induced phosphorylation and activation of p70 S6 kinase. Induces autophagy in yeast and mammalian cell lines. Drives hPSC differentiation to mesendoderm and blood progenitor cells. Also used as a chemical dimerizer; rapamycin and GA3-AM (Cat. No. 5407) chemically inducible dimerization systems are orthogonal. Tocris Bioscience 1292
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB2779]
      Cell process/DNA / RNA & protein synthesis/Genome editing / engineering Hello Bio [HB2779]
      Cell process/Stem cells/Differentiation Hello Bio [HB2779]
      Enzymes Tocris Bioscience 1292
      Enzymes/Kinase/mTOR Hello Bio [HB2779]
      Kinases Tocris Bioscience 1292
      mTOR Tocris Bioscience 1292
      mTOR inhibitor and potent immunosuppressant Hello Bio [HB2779]
      mTOR inhibitor; immunosuppressant Tocris Bioscience 1292

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 973.0±75.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 160.7±6.0 kJ/mol
Flash Point: 542.3±37.1 °C
Index of Refraction: 1.551
Molar Refractivity: 246.7±0.4 cm3
#H bond acceptors: 14
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 2
ACD/LogP: 3.54
ACD/LogD (pH 5.5): 4.21
ACD/BCF (pH 5.5): 939.11
ACD/KOC (pH 5.5): 4671.63
ACD/LogD (pH 7.4): 4.21
ACD/BCF (pH 7.4): 938.17
ACD/KOC (pH 7.4): 4666.98
Polar Surface Area: 195 Å2
Polarizability: 97.8±0.5 10-24cm3
Surface Tension: 51.4±5.0 dyne/cm
Molar Volume: 773.5±5.0 cm3

Click to predict properties on the Chemicalize site


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