ChemSpider 2D Image | 17-Allyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-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-tetraone | C44H69NO12

17-Allyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-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-tetraone

  • Molecular FormulaC44H69NO12
  • Average mass804.018 Da
  • Monoisotopic mass803.481995 Da
  • ChemSpider ID4976056

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 14 of 14 defined stereocentres

More details:

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

(1R,9S,12S,13R,14S,17R,18Z,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
(1R,9S,12S,13R,14S,17R,18Z,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,18Z,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
(1R,9S,12S,13R,14S,17R,18Z,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,18Z,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,18Z,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]
15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycycl ohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9Z,12S,14S,15R,16S,18R,19R,26aS)- [ACD/Index Name]
15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, (3S,4R,5S,8R,9Z,12S,14S,15R,16S,18R,19R,26aS)-
17-Allyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-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-tetraone
(-)-FK 506
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

FK 506 [DBID]
FR 900506 [DBID]
L 679934 [DBID]
AIDS006649 [DBID]
AIDS-006649 [DBID]
CCRIS 7124 [DBID]
FK-506 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Amide; Ester; Drug; Synthetic Compound Toxin, Toxin-Target Database T3D4732

    • 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 Streptomyces tsukubaensis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:61049

    • Bio Activity:

      Enzymes Tocris Bioscience 3631
      Others MedChem Express HY-13756
      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 (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
      Protein Ser/Thr Phosphatases Tocris Bioscience 3631
      Tacrolimus(FK506; FR900506) is a potent immunosuppressive drug often administered to transplant recipient patients and exhibits a variety of adverse cardiovascular effects. MedChem Express
      Tacrolimus(FK506; FR900506) is a potent immunosuppressive drug often administered to transplant recipient patients and exhibits a variety of adverse cardiovascular effects.; IC50 Value: 0.47 nM (Inhibition of lymphocyte proliferation) [1]; Target: ; in vitro: MP and tacrolimus decreased the number of circulating helper-T cells with IC50 values of 23 ng/ml for MP and 6.7 ng/ml for tacrolimus. MedChem Express HY-13756
      Tacrolimus(FK506; FR900506) is a potent immunosuppressive drug often administered to transplant recipient patients and exhibits a variety of adverse cardiovascular effects.;IC50 Value: 0.47 nM (Inhibition of lymphocyte proliferation) [1];Target: ;In vitro: MP and tacrolimus decreased the number of circulating helper-T cells with IC50 values of 23 ng/ml for MP and 6.7 ng/ml for tacrolimus. After coadministration of these drugs, an interaction occurs, but the nature (additive or antagonistic) of this interaction was not clear. The IC50 of tacrolimus for in vitro inhibition of lymphocyte proliferation was 0.39 ng/ml (0.47 nM) and 1.02 ng/ml (2.73 nM) for MP. The maximum percentage of inhibition was 94.6% for tacrolimus and 64.9% for MP [1]. K506 inhibited the proliferation of T cell clones stimulated with specific antigens in a dose-dependent manner, and at about 100-fold lower concentrations than CsA. FK506 inhibited both IL-2 secretion and IL-2 receptor expression of BC.21 after sti MedChem Express HY-13756

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

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

Click to predict properties on the Chemicalize site


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