ChemSpider 2D Image | (-)-borrelidin | C28H43NO6

(-)-borrelidin

  • Molecular FormulaC28H43NO6
  • Average mass489.644 Da
  • Monoisotopic mass489.309052 Da
  • ChemSpider ID4941412
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 9 of 9 defined stereocentres


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

(-)-borrelidin
(-)-borrelidine
(1R,2R)-2-[(2S,4E,6E,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid [ACD/IUPAC Name]
(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyan-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentancarbonsäure [German] [ACD/IUPAC Name]
(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid [ACD/IUPAC Name]
2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid
7184-60-3 [RN]
Acide (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tétraméthyl-18-oxooxacyclooctadéca-4,6-dién-2-yl]cyclopentanecarboxylique [French] [ACD/IUPAC Name]
Borrelidin
Borrelidine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

NSC 216128 [DBID]
B1936_SIGMA [DBID]
B3061_SIGMA [DBID]
BRN 0066270 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Bio Activity:

      Antiangiogenic; inhibits threonyl-tRNA synthetase Tocris Bioscience 4706
      Antibiotic and antiangiogenic. Selectively inhibits threonyl-tRNA synthetase (ThrRS). Exhibits antiangiogenic activity in a mouse model of tumor angiogenesis. Induces apoptosis in capillary tube-formi ng endothelial cells; disrupts capillary tubes and inhibits their formation (IC50 = 0.8 nM in rat aorta). Induces the unfolded protein response (UPR) and apoptosis in oral cancer cells. Tocris Bioscience 4706
      Antibiotic and antiangiogenic. Selectively inhibits threonyl-tRNA synthetase (ThrRS). Exhibits antiangiogenic activity in a mouse model of tumor angiogenesis. Induces apoptosis in capillary tube-forming endothelial cells; disrupts capillary tubes and inhibits their formation (IC50 = 0.8 nM in rat aorta). Induces the unfolded protein response (UPR) and apoptosis in oral cancer cells. Tocris Bioscience 4706
      Antibiotic. Threonyl-tRNA synthetase (THrRS) inhibitor. Hello Bio [HB3810]
      Antibiotic. Threonyl-tRNA synthetase (THrRS) inhibitor. Cyclin-dependent kinase (CDK) inhibitor. Induces the collapse of formed capillary tubes in a dose-dependent fashion. In HUVECs, the capillary tube collapsing activity is mediated by the activation of caspases-3 and -8 and apoptosis induction. Shows anticancer, antiangiogenic and antiviral activity. Hello Bio [HB3810]
      Antibiotics Hello Bio [HB3810]
      Cell signaling/Antibiotics/ Antivirals / antibacterials / immunomodulators Hello Bio [HB3810]
      Enzymes Tocris Bioscience 4706
      Other Synthases/Synthetases Tocris Bioscience 4706
      Synthases/Synthetases Tocris Bioscience 4706

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

Density: 1.1±0.1 g/cm3
Boiling Point: 710.3±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.1 mmHg at 25°C
Enthalpy of Vaporization: 118.7±6.0 kJ/mol
Flash Point: 383.4±32.9 °C
Index of Refraction: 1.539
Molar Refractivity: 133.5±0.4 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 4.31
ACD/LogD (pH 5.5): 3.60
ACD/BCF (pH 5.5): 186.94
ACD/KOC (pH 5.5): 770.80
ACD/LogD (pH 7.4): 1.80
ACD/BCF (pH 7.4): 2.94
ACD/KOC (pH 7.4): 12.11
Polar Surface Area: 128 Å2
Polarizability: 52.9±0.5 10-24cm3
Surface Tension: 50.5±5.0 dyne/cm
Molar Volume: 426.5±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) =  4.36

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  693.49  (Adapted Stein & Brown method)
    Melting Pt (deg C):  302.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.22E-020  (Modified Grain method)
    Subcooled liquid VP: 2.84E-017 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):  0.2121
       log Kow used: 4.36 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  36.108 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters-acid
       Allylic/Vinyl Nitriles-acid
       Vinyl/Allyl Alcohols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.22E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.744E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.36  (KowWin est)
  Log Kaw used:  -13.881  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.241
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3858
   Biowin2 (Non-Linear Model)     :   0.9995
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8595  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9495  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4643
   Biowin6 (MITI Non-Linear Model):   0.0074
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3163
 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):  3.79E-015 Pa (2.84E-017 mm Hg)
  Log Koa (Koawin est  ): 18.241
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  7.92E+008 
       Octanol/air (Koa) model:  4.28E+005 
   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 =  79.1060 E-12 cm3/molecule-sec
      Half-Life =     0.135 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.623 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.711125 E-17 cm3/molecule-sec
      Half-Life =     0.670 Days (at 7E11 mol/cm3)
      Half-Life =     16.074 Hrs
   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    :  389
      Log Koc:  2.590 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 4.36 (estimated)

 Volatilization from Water:
    Henry LC:  3.22E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.024E+012  hours   (1.676E+011 days)
    Half-Life from Model Lake : 4.389E+013  hours   (1.829E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              48.51  percent
    Total biodegradation:        0.46  percent
    Total sludge adsorption:    48.05  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       0.215           2.7          1000       
   Water     21.6            360          1000       
   Soil      72.2            720          1000       
   Sediment  6.05            3.24e+003    0          
     Persistence Time: 523 hr




                    

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