ChemSpider 2D Image | (1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-17-Ethyl-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[22.3.1.0~4,9~]octacos-18-ene-2,3,10,16-tetrone | C43H69NO12

(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-17-Ethyl-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

  • Molecular FormulaC43H69NO12
  • Average mass792.008 Da
  • Monoisotopic mass791.481995 Da
  • ChemSpider ID21169824

  • 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)-17-Ethyl-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-Ethyl-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-Éthyl-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, 8-ethyl-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-met hoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S,4R,5S,8R,9Z,12S,14S,15R,16S,18R,19R,26aS)- [ACD/Index Name]
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
[104987-12-4] [RN]
10386-84-2 [RN]
11011-38-4 [RN]
Ascomycin [Wiki]
More...

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

A3835_SIGMA [DBID]
FK 520 [DBID]
FR 900520 [DBID]
FR-900520 [DBID]
L 683590 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      Others TargetMol T2481

    • Chemical Class:

      A macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:29582

    • Bio Activity:

      Analog of FK 506 (Cat. No. 3631); binds to FK 506-binding protein 12 (FKBP12) in order to inhibit calcineurin phosphatase activity (IC50 = 49 nM) and activation of nuclear factor of activated T cells (NFAT). Displays antifungal and immunosuppressive activities. Tocris Bioscience 4210
      Antifungal MedChem Express HY-13557
      Anti-infection MedChem Express HY-13557
      Anti-infection; MedChem Express HY-13557
      Ascomycin(Immunomycin, FR-900520, FK520) is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. MedChem Express HY-13557, http://www.medchemexpress.com/ascomycin.html
      Ascomycin(Immunomycin, FR-900520, FK520) is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. ;IC50 Value: 0.55 nM [1];Target: ;In vitro: When we used either CD4+CD8+ thymocytes or peripheral T cells activated by phorbol ester and ionomycin, the cell surface induction of CD5 was also partially blocked by CsA, FK-520 and rapamycin [2]. Ascomycinalso had a 3-fold lower immunosuppressive potency in a popliteal lymph node hyperplasia assay, resulting in an equivalent therapeutic index consistent with a common mechanistic dependence on calcineurin inhibition [3].;In vivo: In 14-day studies, nephrotoxicity was not induced by continuous i.p. infusion of ascomycin at 10 mg/kg/day or daily oral administration (up to 50 mg/kg/day) in rats on a normal diet, nor by continuous i.v. infusion (up to 6 mg/kg/day) in rats on a low salt diet to enhance susceptibility [3]. MedChem Express HY-13557
      Enzymes Tocris Bioscience 4210
      Others TargetMol T2481
      Phosphatases Tocris Bioscience 4210
      Protein Ser/Thr Phosphatases Tocris Bioscience 4210

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

Density: 1.2±0.1 g/cm3
Boiling Point: 868.3±75.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 143.4±6.0 kJ/mol
Flash Point: 478.9±37.1 °C
Index of Refraction: 1.546
Molar Refractivity: 209.7±0.4 cm3
#H bond acceptors: 13
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 2
ACD/LogP: 3.81
ACD/LogD (pH 5.5): 3.92
ACD/BCF (pH 5.5): 557.22
ACD/KOC (pH 5.5): 3215.17
ACD/LogD (pH 7.4): 3.91
ACD/BCF (pH 7.4): 555.72
ACD/KOC (pH 7.4): 3206.50
Polar Surface Area: 178 Å2
Polarizability: 83.1±0.5 10-24cm3
Surface Tension: 51.4±5.0 dyne/cm
Molar Volume: 661.9±5.0 cm3

Click to predict properties on the Chemicalize site


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