InChI=1/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

Inherent Properties, Identifiers and References

ChemSpider ID:	50
Empirical Formula:	C₅H₆O₅
Molecular Weight:	146.0981
Nominal Mass:	146 Da
Average Mass:	146.0981 Da
Monoisotopic Mass:	146.021523 Da

Systematic Name:

2-oxopentanedioic acid

SMILES:

O=C(O)C(=O)CCC(=O)O

InChI:

InChI=1/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

InChIKey:

KPGXRSRHYNQIFN-UHFFFAOYAN

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Supplemental Information

Links & References

Balibar et al.. Terrequinone A biosynthesis through L-tryptophan oxidation, dimerization and bis-prenylation, Nature Chemical Biology, doi: 10.1038/NChemBio.2007.20, published online 12 August 2007.

[DOI: 10.1038/NChemBio.2007.20]

Macheboeuf et al.. Structural and Mechanistic Basis of Penicillin Binding Protein Inhibition by Lactivicins, Nature Chemical Biology, doi: 10.1038/NChemBio.2007.21, published online 5 August 2007.

[DOI: 10.1038/NChemBio.2007.21]

User Data

experimental physchem properties

Melting Point: 113-115

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Boiling Point: 323

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

miscellaneous

Appearance: white to pale yellow crystalline powder

Visual appearance of the given substance.

Safety: WARNING: Irritates lungs, eyes, skin

See Chemical Safety

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ketoglutaric acid

2-Oxo-1,5-pentanedioate

2-oxopentanedioate

Oxoglutarate

Pentanedioic acid, 2-oxo- (9CI)

.alpha.-Ketoglutaric acid

.alpha.-Oxoglutaric acid

15303-07-8 [RN]

17091-15-5 [RN]

206-330-3 [EINECS/ELINCS]

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Predicted Properties

LogP:	ACD/LogP: -1.43 XLogP: -1.10 ALOGPS: -0.60	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-5.33	ACD/LogD (pH 7.4):	-6.17
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1	ACD/KOC (pH 7.4):	1
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	4	Polar Surface Area:	69.67 Å²
Index of Refraction:	1.494	Molar Refractivity:	28.37 cm³
Molar Volume:	97.4 cm³	Polarizability:	11.24 10^-24cm³
Surface Tension:	67.9 dyne/cm	Density:	1.499 g/cm³
Flash Point:	177 °C	Enthalpy of Vaporization:	64.8 kJ/mol
Boiling Point:	345.6 °C at 760 mmHg	Vapour Pressure:	1.08E-05 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -2.08

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  323.26  (Adapted Stein & Brown method)
    Melting Pt (deg C):  117.34  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.18E-005  (Modified Grain method)
    MP  (exp database):  115.5 deg C
    Subcooled liquid VP: 0.000563 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: -2.08 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8.3106e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.15E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.380E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -2.08  (KowWin est)
  Log Kaw used:  -12.056  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.976
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8234
   Biowin2 (Non-Linear Model)     :   0.9021
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.6055  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.4081  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7386
   Biowin6 (MITI Non-Linear Model):   0.8078
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.2616
 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):  0.0751 Pa (0.000563 mm Hg)
  Log Koa (Koawin est  ): 9.976
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4E-005 
       Octanol/air (Koa) model:  0.00232 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00144 
       Mackay model           :  0.00319 
       Octanol/air (Koa) model:  0.157 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   4.6336 E-12 cm3/molecule-sec
      Half-Life =     2.308 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.700 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.00231 (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: -2.08 (estimated)

 Volatilization from Water:
    Henry LC:  2.15E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.292E+010  hours   (1.371E+009 days)
    Half-Life from Model Lake : 3.591E+011  hours   (1.496E+010 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       7.59e-007       55.4         1000       
   Water     34.5            208          1000       
   Soil      65.5            416          1000       
   Sediment  0.0596          1.87e+003    0          
     Persistence Time: 387 hr

Spectra

Type: HNMR

Associated Hyperlink: http://mmcd.nmrfam.wisc.edu/rawnmr/expnmr_00021_1.tar

Comments: Madison Metabolomics Consortium Database Spectrum, Q. Cui, I. A. et al; "Metabolite identification via the Madison Metabolomics Consortium Database", Nature Biotechnology, 26,162 (2008)

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Type: CNMR

Associated Hyperlink: http://mmcd.nmrfam.wisc.edu/rawnmr/expnmr_00021_3.tar

Comments: Madison Metabolomics Consortium Database Spectrum, Q. Cui, et al; "Metabolite identification via the Madison Metabolomics Consortium Database", Nature Biotechnology, 26,162 (2008)

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