ChemSpider 2D Image | S-[(2R,3S,4S,6S)-6-({[(2R,3S,4S,5R,6R)-5-{[(2S,4S,5S)-5-(Ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5E,9R,13Z)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl) ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl]amino}oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl] 4-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-me thoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name) | C55H74IN3O21S4

S-[(2R,3S,4S,6S)-6-({[(2R,3S,4S,5R,6R)-5-{[(2S,4S,5S)-5-(Ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5E,9R,13Z)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl) ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl]amino}oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl] 4-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-me thoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name)

  • Molecular FormulaC55H74IN3O21S4
  • Average mass1368.348 Da
  • Monoisotopic mass1367.274170 Da
  • ChemSpider ID57251296

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 19 of 19 defined stereocentres

More details:

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

108212-75-5 [RN]
Calicheamicin [Wiki]
  • Miscellaneous

    • Bio Activity:

      ADCs cytotoxin DNA alkylator/crosslinker MedChem Express HY-19609
      Antibody-drug conjugates/ADCs Related; Cell Cycle/DNA Damage; MedChem Express HY-19609
      Calicheamicin is a potent DNA-binding cytotoxic antibiotic.;Target: AntibacterialCalicheamicin being the most notable enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora. Calicheamicin targets DNA and cause strand scission. Calicheamicin binds with DNA in the minor groove, wherein they then undergo a reaction analogous to the Bergman cyclization to generate a diradical species. This diradical, 1,4-didehydrobenzene, then abstracts hydrogen atoms from the deoxyribose (sugar) backbone of DNA, which ultimately leads to strand scission. The specificity of binding of Calicheamicin to the minor groove of DNA was demonstrated to be due to the aryltetrasaccharide group of the molecule. MedChem Express HY-19609

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.662
Molar Refractivity: 322.7±0.4 cm3
#H bond acceptors: 24
#H bond donors: 8
#Freely Rotating Bonds: 24
#Rule of 5 Violations: 4
ACD/LogP: 11.89
ACD/LogD (pH 5.5): 5.28
ACD/BCF (pH 5.5): 1176.52
ACD/KOC (pH 5.5): 794.35
ACD/LogD (pH 7.4): 6.22
ACD/BCF (pH 7.4): 10321.91
ACD/KOC (pH 7.4): 6969.10
Polar Surface Area: 410 Å2
Polarizability: 127.9±0.5 10-24cm3
Surface Tension: 77.1±5.0 dyne/cm
Molar Volume: 871.5±5.0 cm3

Click to predict properties on the Chemicalize site


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