ChemSpider 2D Image | Amrubicin | C25H25NO9

Amrubicin

  • Molecular FormulaC25H25NO9
  • Average mass483.467 Da
  • Monoisotopic mass483.152924 Da
  • ChemSpider ID2299344

  • defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(1S,3S)-3-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 2-deoxy-β-D-erythro-pentopyranoside [ACD/IUPAC Name]
(1S,3S)-3-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl-2-desoxy-β-D-erythro-pentopyranosid [German] [ACD/IUPAC Name]
(1S,3S)-3-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxy-β-D-erythro-pentopyranoside
110267-81-7 [RN]
2-Désoxy-β-D-érythro-pentopyranoside de (1S,3S)-3-acétyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tétracényle [French] [ACD/IUPAC Name]
5,12-Naphthacenedione, 9-acetyl-9-amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-, (7S,9S)- [ACD/Index Name]
Amrubicin [INN] [USAN] [Wiki]
Calsed [Trade name]
(1S,3S)-3-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl2-deoxy-?-D-erythro-pentopyranoside
(7S,9S)-9-acetyl-9-amino-7-(((2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

6802 [DBID]
93N13LB4Z2 [DBID]
SM-5887 [DBID]
UNII:93N13LB4Z2 [DBID]
UNII-93N13LB4Z2 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A synthetic anthracycline antibiotic with molecular formula C25H25NO9. A specific inhibitor of topoisomerase II, it is used (particularly as the hydrochloride salt) in the treatment of cancer, especia lly lung cancer, where it is a prodrug for the active metabolite, ambrucinol. ChEBI CHEBI:135779

    • Bio Activity:

      Amrubicin(SM-5887) is a novel anthracycline derivative for treatment of bladder carcinoma. MedChem Express
      Amrubicin(SM-5887) is a novel anthracycline derivative for treatment of bladder carcinoma.; Target: Others; Amrubicin (SM-5887) is an anthracycline used in the treatment of lung cancer. MedChem Express HY-B0067
      Amrubicin(SM-5887) is a novel anthracycline derivative for treatment of bladder carcinoma.;Target: Amrubicin (SM-5887) is an anthracycline used in the treatment of lung cancer. The distribution of SM-5887 in the bladder mucosa and muscular layer was almost equal, but the concentration of its active metabolite, 13-OH derivative, was 5 to 10 times higher in the bladder mucosa than in the bladder muscular layer. The distributions of SM-5887 in the organs other than the bladder, that is, the cortex and medulla of kidney, heart, lung, liver, and spleen, were very low, and those of a 13-OH active metabolite were even lower. In addition, SM-5887 barely affected the normal bladder mucosa. In dogs instilled with 80 mg of SM-5887, no histological change was observed in the bladder mucosa and submucosal layer even after 6-hour retention at the highest concentration of 8,000 micrograms/ml [1]. phase II clinical trial of SM-5887, a new totally synthesized anthracycline derivative, was car MedChem Express HY-B0067
      Others MedChem Express HY-B0067

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

Density: 1.6±0.1 g/cm3
Boiling Point: 717.8±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 110.1±3.0 kJ/mol
Flash Point: 387.9±32.9 °C
Index of Refraction: 1.720
Molar Refractivity: 119.0±0.4 cm3
#H bond acceptors: 10
#H bond donors: 6
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 2
ACD/LogP: 2.64
ACD/LogD (pH 5.5): 1.59
ACD/BCF (pH 5.5): 7.79
ACD/KOC (pH 5.5): 118.81
ACD/LogD (pH 7.4): 1.61
ACD/BCF (pH 7.4): 8.06
ACD/KOC (pH 7.4): 122.90
Polar Surface Area: 177 Å2
Polarizability: 47.2±0.5 10-24cm3
Surface Tension: 95.4±5.0 dyne/cm
Molar Volume: 301.2±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.53

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  712.51  (Adapted Stein & Brown method)
    Melting Pt (deg C):  311.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.92E-021  (Modified Grain method)
    Subcooled liquid VP: 6.5E-018 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  135.3
       log Kow used: 1.53 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  9.9052e+005 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Phenols
       Quinone/Hydroquinone

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.50E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.843E-023 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.53  (KowWin est)
  Log Kaw used:  -24.459  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  25.989
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4168
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2161  (months      )
   Biowin4 (Primary Survey Model) :   3.2236  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2459
   Biowin6 (MITI Non-Linear Model):   0.0061
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3757
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  8.67E-016 Pa (6.5E-018 mm Hg)
  Log Koa (Koawin est  ): 25.989
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.46E+009 
       Octanol/air (Koa) model:  2.39E+013 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 109.1504 E-12 cm3/molecule-sec
      Half-Life =     0.098 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.176 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  16.83
      Log Koc:  1.226 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = -0.361 (BCF = 0.4352)
       log Kow used: 1.53 (estimated)

 Volatilization from Water:
    Henry LC:  8.5E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.515E+023  hours   (6.311E+021 days)
    Half-Life from Model Lake : 1.652E+024  hours   (6.884E+022 days)

 Removal In Wastewater Treatment:
    Total removal:               1.98  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.89  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       2.56e-008       2.35         1000       
   Water     34              1.44e+003    1000       
   Soil      66              2.88e+003    1000       
   Sediment  0.0887          1.3e+004     0          
     Persistence Time: 1.51e+003 hr

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