InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10-11H,1H2/t2-,5+/m0/s1

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Search term: TYQCGQRIZGCHNB-JLAZNSOCBA
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Inherent Properties, Identifiers and References

ChemSpider ID:	5581
Empirical Formula:	C₆H₈O₆
Molecular Weight:	176.1241
Nominal Mass:	176 Da
Average Mass:	176.1241 Da
Monoisotopic Mass:	176.032088 Da

Systematic Name:

(2R)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxy-furan-3-one

SMILES:

O=C1C(\O)=C(\O)O[C@@H]1[C@@H](O)CO

InChI:

InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10-11H,1H2/t2-,5+/m0/s1

InChIKey:

TYQCGQRIZGCHNB-JLAZNSOCBA

Std. InChI:

InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10-11H,1H2/t2-,5+/m0/s1

Std. InChIKey:

TYQCGQRIZGCHNB-JLAZNSOCSA-N

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Supplemental Information

Links & References

Dzygiel Pawel. Efficient resolution of racemic N-benzyl β3-amino acids by iterative liquid–liquid extraction with a chiral (salen)cobalt(iii) complex as enantioselective selector, Organic & Biomolecular Chemistry, 2007

[DOI: 10.1039/b711477j]

Jansson et al.. A mammalian functional nitrate reductase that regulates nitrite and nitric oxide homeostasis , Nature Chemical Biology, doi: 10.1038/nchembio.92, published online 30 May 2008.

[DOI: 10.1038/nchembio.92]

Names and Synonyms

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

(2R)-2-[(1S)-1,2-Dihydroxyethyl]-4,5-dihydroxy-furan-3-one

50-81-7 [RN]

L-threo-hex-1-enofuranos-3-ulose

L-threo-Hex-1-eofuranos-3-ulose

(R)-2-((S)-1,2-dihydroxyethyl)-4,5-dihydroxyfuran-3(2H)-one

(R)-5-((S)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-5H-furan-2-one

(R)-5-((S)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one

3-Keto-L-gulofuranolactone

3-Oxo-L-gulofuranolactone

3-Oxo-L-gulofuranolactone (enol form)

More...

Database ID(s)

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

ACD/Labs Predicted Properties

ACD/LogP:	-2.65	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-4.27	ACD/LogD (pH 7.4):	-5.86
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:	6	#H bond donors:	4
#Freely Rotating Bonds:	6	Polar Surface Area:	63.22 Å²
Index of Refraction:	1.711	Molar Refractivity:	35.26 cm³
Molar Volume:	90.1 cm³	Polarizability:	13.97 10^-24cm³
Surface Tension:	140.5 dyne/cm	Density:	1.954 g/cm³
Flash Point:	180.4 °C	Enthalpy of Vaporization:	77.28 kJ/mol
Boiling Point:	415.8 °C at 760 mmHg	Vapour Pressure:	1.18E-08 mmHg at 25°C

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -1.31

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  403.20  (Adapted Stein & Brown method)
    Melting Pt (deg C):  152.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.31E-009  (Modified Grain method)
    Subcooled liquid VP: 2.6E-008 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):  7.624e+005
       log Kow used: -1.31 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.502e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.83E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.982E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.31  (KowWin est)
  Log Kaw used:  -6.705  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.395
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9581
   Biowin2 (Non-Linear Model)     :   0.7496
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.4187  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.0795  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.9631
   Biowin6 (MITI Non-Linear Model):   0.9156
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6176
 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):  3.47E-006 Pa (2.6E-008 mm Hg)
  Log Koa (Koawin est  ): 5.395
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.865 
       Octanol/air (Koa) model:  6.1E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.969 
       Mackay model           :  0.986 
       Octanol/air (Koa) model:  4.88E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 172.8393 E-12 cm3/molecule-sec
      Half-Life =     0.062 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.743 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.875000 E-17 cm3/molecule-sec
      Half-Life =     1.310 Days (at 7E11 mol/cm3)
      Half-Life =     31.433 Hrs
   Fraction sorbed to airborne particulates (phi): 0.977 (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: -1.31 (estimated)

 Volatilization from Water:
    Henry LC:  4.83E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.609E+005  hours   (6703 days)
    Half-Life from Model Lake : 1.755E+006  hours   (7.313E+004 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       0.25            1.42         1000       
   Water     42.3            208          1000       
   Soil      57.4            416          1000       
   Sediment  0.0733          1.87e+003    0          
     Persistence Time: 248 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 1, 0, 0, 0, 3, 1, 0, 3, 6, 0, 0, 4, 0, 2, 2, 1, 1, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.72
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.02
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Kinases	TK, thymidine kinase	1kim	0.01
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	Thrombin	1ba8	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00