ChemSpider 2D Image | Validamycin A | C20H35NO13

Validamycin A

  • Molecular FormulaC20H35NO13
  • Average mass497.491 Da
  • Monoisotopic mass497.210846 Da
  • ChemSpider ID391771

  • defined stereocentres - 14 of 14 defined stereocentres

More details:

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

Validamycin A
(1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino}cyclohexyl β-D-glucopyranoside [ACD/IUPAC Name]
(1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino}cyclohexyl-β-D-glucopyranosid [German] [ACD/IUPAC Name]
313E9620QS
MFCD09028089 [MDL number]
NM7540000
β-D-Glucopyranoside de (1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxyméthyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxyméthyl)-2-cyclohexén-1-yl]amino}cyclohexyle [French] [ACD/IUPAC Name]
β-D-Glucopyranoside, (1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]cyclohexyl [ACD/Index Name]
(+)-validamycin A
(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexyl β-D-glucopyranoside
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C12112 [DBID]
  • Miscellaneous

    • Chemical Class:

      A member of the class of validamycins that is (1<stereo>R</stereo>,2<stereo>S</stereo>,3<stereo>S</stereo>,4<stereo>S</stereo>,6<stereo>R</stereo>)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its <stereo>beta</stereo>-<stereo>D</stereo>-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1<stereo >R</stereo>,4<stereo>R</stereo>,5<stereo>R</stereo>,6<stereo>S</stereo>)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by <ital>Streptomyces hygrosco picus</ital>. ChEBI CHEBI:29703
      A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in ; which the hydroxy group at position 1 has been converted to its beta-D-glucoside an d in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:29703
      A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces h ygroscopicus. ChEBI CHEBI:29703

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

Density: 1.7±0.1 g/cm3
Boiling Point: 813.7±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.6 mmHg at 25°C
Enthalpy of Vaporization: 134.7±6.0 kJ/mol
Flash Point: 445.9±34.3 °C
Index of Refraction: 1.689
Molar Refractivity: 111.9±0.4 cm3
#H bond acceptors: 14
#H bond donors: 12
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 2
ACD/LogP: -5.43
ACD/LogD (pH 5.5): -6.17
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.86
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 253 Å2
Polarizability: 44.4±0.5 10-24cm3
Surface Tension: 112.5±5.0 dyne/cm
Molar Volume: 293.0±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) =  -8.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  809.91  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.06E-026  (Modified Grain method)
    Subcooled liquid VP: 4.13E-022 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):  1e+006
       log Kow used: -8.32 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1e+006 mg/L ( deg C)
        Exper. Ref:  TOMLIN,C (1994) ;readily soluble

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  1000000.00
       Exper. Ref:  TOMLIN,C (1994) ;readily soluble

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.86E-027  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.276E-032 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -8.32  (KowWin est)
  Log Kaw used:  -25.119  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.799
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.7158
   Biowin2 (Non-Linear Model)     :   0.9235
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.8665  (days        )
   Biowin4 (Primary Survey Model) :   4.5777  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   1.3892
   Biowin6 (MITI Non-Linear Model):   0.1753
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  2.3960
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.51E-020 Pa (4.13E-022 mm Hg)
  Log Koa (Koawin est  ): 16.799
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.45E+013 
       Octanol/air (Koa) model:  1.55E+004 
   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 = 342.0620 E-12 cm3/molecule-sec
      Half-Life =     0.031 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    22.514 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   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    :  439.1
      Log Koc:  2.643 

 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: -8.32 (estimated)

 Volatilization from Water:
    Henry LC:  1.86E-027 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.021E+023  hours   (2.925E+022 days)
    Half-Life from Model Lake : 7.659E+024  hours   (3.191E+023 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       0.0014          0.345        1000       
   Water     26.9            55.9         1000       
   Soil      73.1            112          1000       
   Sediment  0.0345          503          0          
     Persistence Time: 123 hr

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