ChemSpider 2D Image | Danshensu | C9H10O5

Danshensu

  • Molecular FormulaC9H10O5
  • Average mass198.173 Da
  • Monoisotopic mass198.052826 Da
  • ChemSpider ID9775399

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

(2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid [ACD/IUPAC Name]
(2R)-3-(3,4-Dihydroxyphenyl)-2-hydroxypropansäure [German] [ACD/IUPAC Name]
4GF33A5PAJ
76822-21-4 [RN]
Acide (2R)-3-(3,4-dihydroxyphényl)-2-hydroxypropanoïque [French] [ACD/IUPAC Name]
Benzenepropanoic acid, α,3,4-trihydroxy-, (αR)- [ACD/Index Name]
Danshensu
Salvianic acid A
(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxy-propanoic acid
(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxy-propionic acid
More...
  • Miscellaneous

    • Chemical Class:

      A (2<stereo>R</stereo>)-2-hydroxy monocarboxylic acid that is (<stereo>R</stereo>)-lactic acid substituted at position 3 by a 3,4-dihydroxyphenyl group. ChEBI CHEBI:71572
      A (2R)-2-hydroxy monocarboxylic acid that is (R)-lactic acid substituted at position 3 by a 3,4-dihydroxyphenyl group. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71572, CHEBI:71572

    • Bio Activity:

      Danshensu, an active ingredient of Salvia miltiorrhiza, shows wide cardiovascular benefit.;IC50 value:;Target:;In vitro: Danshensu (DSS) significantly decreased the level of the marker enzymes (creatine kinase and lactate dehydrogenase) from the coronary effluents and myocardial infarction size. This could markedly contribute to the recovery of cardiac function after I/R injury. DSS also had ROS scavenging activity and boosted endogenous antioxidants such as SOD, CAT, MDA, GSH-PX and HO-1 activities by activating nuclear factor erythroid-2-related factor 2 (Nrf2) signaling pathway which was mediated by Akt and ERK1/2 in western blot analysis[2].;In vivo: Acute treatment with a single dose of danshensu in rats with normal tHcy did not change plasma tHcy. In contrast, danshensu significantly lowered tHcy in rats with elevated tHcy. The relatively higher cysteine and glutathione levels after treatment with danshensu indicated that its tHcy-lowering effect was via increased activity o MedChem Express HY-N1913

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

Density: 1.5±0.1 g/cm3
Boiling Point: 481.5±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 78.6±3.0 kJ/mol
Flash Point: 259.1±23.8 °C
Index of Refraction: 1.659
Molar Refractivity: 47.3±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -0.29
ACD/LogD (pH 5.5): -1.92
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.33
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 98 Å2
Polarizability: 18.7±0.5 10-24cm3
Surface Tension: 85.5±3.0 dyne/cm
Molar Volume: 128.1±3.0 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) =  0.10

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  394.52  (Adapted Stein & Brown method)
    Melting Pt (deg C):  163.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.01E-008  (Modified Grain method)
    Subcooled liquid VP: 2.68E-007 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: 0.10 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.91E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.634E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.10  (KowWin est)
  Log Kaw used:  -14.392  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.492
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1709
   Biowin2 (Non-Linear Model)     :   0.9873
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.3237  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0877  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5116
   Biowin6 (MITI Non-Linear Model):   0.5140
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7431
 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):  3.57E-005 Pa (2.68E-007 mm Hg)
  Log Koa (Koawin est  ): 14.492
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.084 
       Octanol/air (Koa) model:  76.2 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.752 
       Mackay model           :  0.87 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  65.3638 E-12 cm3/molecule-sec
      Half-Life =     0.164 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.964 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.811 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: 0.10 (estimated)

 Volatilization from Water:
    Henry LC:  9.91E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.317E+012  hours   (3.465E+011 days)
    Half-Life from Model Lake : 9.073E+013  hours   (3.78E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       1.67e-008       3.93         1000       
   Water     33.9            208          1000       
   Soil      66              416          1000       
   Sediment  0.0594          1.87e+003    0          
     Persistence Time: 389 hr

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