ChemSpider 2D Image | Tacrolimus | C44H69NO12

Tacrolimus

  • Molecular FormulaC44H69NO12
  • Average mass804.018 Da
  • Monoisotopic mass803.481995 Da
  • ChemSpider ID393220
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 14 of 14 defined stereocentres


More details:



Featured data source



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

(-)-FK 506
(-)-Tacrolimus
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-Dihydroxy-12-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl}-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-en-1-yl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en-2,3,10,16-tetron [German]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl}-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-en-1-yl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-méthoxycyclohexyl]-1-méthyléthényl}-23,25-diméthoxy-13,19,21,27-tétraméthyl-17-prop-2-én-1-yl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ène-2,3,10,16-tétrone [French]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-en-2,3,10,16-tetron [German] [ACD/IUPAC Name]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone [ACD/IUPAC Name]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-méthoxycyclohexyl]-1-propén-2-yl}-23,25-diméthoxy-13,19,21,27-tétraméthyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-ène-2,3,10,16-tétrone [French] [ACD/IUPAC Name]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C01375 [DBID]
FK 506 [DBID]
FK-506 [DBID]
FR-900506 [DBID]
L-679934 [DBID]
NChemBio.2007.16-comp1 [DBID]
nchembio849-comp2 [DBID]
UN2811 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 2263
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2263
      no pictogram Axon Medchem 2263
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2263
      Warning Axon Medchem 2263
    • Chemical Class:

      Tacrolimus is a macrolide containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria <ital>Streptomyces tsukubaensis</ ital>. ChEBI CHEBI:61049
    • Compound Source:

      Streptomyces tsukubaensis Microsource [01503968]
    • Bio Activity:

      Enzymes Tocris Bioscience 3631
      Phosphatases Tocris Bioscience 3631
      Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC50 = 1 nM), IL-3, IL-4, IL-6 (IC5 0 = 35 nM), GM-CSF, TNF? (IC50 = 10 nM), IFN? and Myc from activated T cells in vitro. Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo. Analog (ascomycin, Cat. N o. 4210) also available. Tocris Bioscience 3631
      Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC50 = 1 nM), IL-3, IL-4, IL-6 (IC50 = 35 nM), GM-CSF, TNF? (IC50 = 10 nM), IFN? and Myc from activated T cells in vitro. Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo. Analog (ascomycin, Cat. No. 4210) also available. Tocris Bioscience 3631
      Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC50 = 1 nM), IL-3, IL-4, IL-6 (IC50 = 35 nM), GM-CSF, TNFalpha (IC50 = 10 nM), IFNgamma and Myc from activated T cells in vitro. Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo. Analog (ascomycin, Cat. No. 4210) also available. Tocris Bioscience 3631
      Potent calcineurin (protein phosphatase 2B) inhibitor that requires FK 506-binding protein 12 (FKBP12) for activity (IC50 = 3 nM). Inhibits secretion of IL-1, IL-2 (IC50 = 1 nM), IL-3, IL-4, IL-6 (IC50 = 35 nM), GM-CSF, TNFalpha (IC50 = 10 nM), IFNgamma and Myc from activated T cells in vitro. Exhibits potent immunosuppressive, neuroprotective and anticonvulsant activity in vivo. Analog also available. Tocris Bioscience 3631
      Potent calcineurin inhibitor; immunosuppressant Tocris Bioscience 3631
      Protein Ser/Thr Phosphatases Tocris Bioscience 3631

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point: 871.7±75.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 143.9±6.0 kJ/mol
Flash Point: 481.0±37.1 °C
Index of Refraction: 1.549
Molar Refractivity: 214.1±0.4 cm3
#H bond acceptors: 13
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: 3.96
ACD/LogD (pH 5.5): 4.09
ACD/BCF (pH 5.5): 762.47
ACD/KOC (pH 5.5): 4024.32
ACD/LogD (pH 7.4): 4.09
ACD/BCF (pH 7.4): 760.41
ACD/KOC (pH 7.4): 4013.43
Polar Surface Area: 178 Å2
Polarizability: 84.9±0.5 10-24cm3
Surface Tension: 51.3±5.0 dyne/cm
Molar Volume: 673.1±5.0 cm3

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