ChemSpider 2D Image | pasireotide | C58H66N10O9

pasireotide

  • Molecular FormulaC58H66N10O9
  • Average mass1047.206 Da
  • Monoisotopic mass1046.501465 Da
  • ChemSpider ID8117062
  • defined stereocentres - 7 of 7 defined stereocentres


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396091-73-9 [RN]
8384
98H1T17066
cyclo((4R)-4-(2-aminoethylcarbamoyloxy)-L-prolyl-L-phenylglycyl-D-tryptophyl-L-lysyl-4-O-benzyl-L-tyrosyl-L- phenylalanyl-)
Cyclo[(2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-(phenylmethyl)-L-tyrosyl-L-phenylalanyl-(4R)-4-[[[(2-aminoethyl)amino]carbonyl]oxy]-L-prolyl] [ACD/Index Name]
Cyclo[(2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-benzyl-L-tyrosyl-L-phenylalanyl-(4R)-4-{[(2-aminoethyl)carbamoyl]oxy}-L-prolyl] [ACD/IUPAC Name]
Cyclo[(2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-benzyl-L-tyrosyl-L-phenylalanyl-(4R)-4-{[(2-aminoethyl)carbamoyl]oxy}-L-prolyl] [German] [ACD/IUPAC Name]
Cyclo[(2S)-2-phénylglycyl-D-tryptophyl-L-lysyl-O-benzyl-L-tyrosyl-L-phénylalanyl-(4R)-4-{[(2-aminoéthyl)carbamoyl]oxy}-L-prolyl] [French] [ACD/IUPAC Name]
pasireotida [Spanish] [INN]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A six-membered homodetic cyclic peptide composed from <stereo>L</stereo>-phenylglycyl, <stereo>D</stereo>-tryptophyl, <stereo>L</stereo>-lysyl, <element>O</element>-benzyl-<stereo>L</stereo>-tyrosyl, <stereo>L</stereo>-phenylalanyl and modified <stereo>L</stereo>-hydroxyproline residues joined in sequence. A somatostatin analogue with pharmacologic properties mimicking those of the natural hormone somatostatin; used (as its diaspartate salt) for treatment of Cushing's disease. ChEBI CHEBI:72312
    • Bio Activity:

      GPCR/G protein MedChem Express HY-16381
      GPCR/G protein; MedChem Express HY-16381
      Pasireotide(SOM 230) is a stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1/2/3/4/5, pKi=8.2/9.0/9.1/<7.0/9.9 respect ively). MedChem Express
      Pasireotide(SOM 230) is a stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1/2/3/4/5, pKi=8.2/9.0/9.1/<7.0/9.9 respectively).; IC50 value: 8.2/9.0/9.1/<7.0/9.9(pKi, sst1/2/3/4/5) [1]; in vitro: SOM230 showed a lower potency of GH release inhibition (IC(50), 0.5 nM), compared with OCT (IC(50), 0.02 nM) and SRIF-14 (IC(50), 0.02 nM). MedChem Express HY-16381
      Pasireotide(SOM 230) is a stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1/2/3/4/5, pKi=8.2/9.0/9.1/<7.0/9.9 respectively).;IC50 value: 8.2/9.0/9.1/<7.0/9.9(pKi, sst1/2/3/4/5) [1];In vitro: SOM230 showed a lower potency of GH release inhibition (IC(50), 0.5 nM), compared with OCT (IC(50), 0.02 nM) and SRIF-14 (IC(50), 0.02 nM). A positive correlation was found between sst(2) but not sst(5) mRNA levels in the adenoma cells and the inhibitory potency of OCT on GH release in vivo and in vitro, and the effects of SOM230 and SRIF-14 in vitro [2]. In cultures of human fetal pituitary cells, SOM230 inhibited GH secretion by 42 +/- 9% (P = 0.002) but had no effect on TSH release. SOM230 inhibited GH release from GH-secreting adenoma cultures by 34 +/- 8% (P = 0.002), PRL by 35 +/- 4% from PRL-secreting adenomas (P = 0.01), and alpha-subunit secretion from nonfunctioning pituitary adenomas by 46 +/- 18% (P = MedChem Express HY-16381
      Somatostatin Receptor MedChem Express HY-16381

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

Density: 1.4±0.1 g/cm3
Boiling Point: 1351.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization: 205.2±3.0 kJ/mol
Flash Point: 771.1±34.3 °C
Index of Refraction: 1.680
Molar Refractivity: 290.6±0.4 cm3
#H bond acceptors: 19
#H bond donors: 11
#Freely Rotating Bonds: 18
#Rule of 5 Violations: 3
ACD/LogP: 2.79
ACD/LogD (pH 5.5): -1.39
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -1.28
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 281 Å2
Polarizability: 115.2±0.5 10-24cm3
Surface Tension: 75.3±5.0 dyne/cm
Molar Volume: 768.7±5.0 cm3

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