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ChemSpider 2D Image | Orotic acid | C5H4N2O4

Orotic acid

  • Molecular FormulaC5H4N2O4
  • Average mass156.096 Da
  • Monoisotopic mass156.017105 Da
  • ChemSpider ID942

More details:



Featured data source



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

1,2,3,6-TETRAHYDRO-2,6-DIOXO-4-PYRIMIDINECARBOXYLIC ACID
1,2,3,6-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid
2,6-dihydroxypyrimidine-4-carboxylic acid
2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidincarbonsäure [German] [ACD/IUPAC Name]
2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid [ACD/IUPAC Name]
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
200-619-8 [EINECS]
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo- [ACD/Index Name]
65-86-1 [RN]
More...

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

3502 [DBID]
61H4T033E5 [DBID]
MFCD00006027 [DBID]
RM3180000 [DBID]
AB-323/25048164 [DBID]
AI3-25478 [DBID]
AIDS011908 [DBID]
AIDS-011908 [DBID]
AIDS160397 [DBID]
AIDS-160397 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Ester; Food Toxin; Metabolite; Animal Toxin; Natural Compound Toxin, Toxin-Target Database T3D4292
    • Safety:

      22-36/38 Alfa Aesar B25349
      26-36/37 Alfa Aesar B25349
      GHS07 Biosynth W-104782
      H302; H315; H319; H335 Biosynth W-104782
      H302-H315-H319 Alfa Aesar B25349
      HARMFUL / IRRITANT Alfa Aesar B25349
      Harmful/Irritant SynQuest 4H53-1-X2, 60850
      IRRITANT Matrix Scientific 082651
      P261; P305+P351+P338 Biosynth W-104782
      P280-P305+P351+P338-P362-P301+P312-P321-P501a Alfa Aesar B25349
      Warning Alfa Aesar B25349
      Warning Biosynth W-104782
      WARNING: Irritates skin and eyes, harmful if swallowed Alfa Aesar B25349
    • Target Organs:

      DHOase inhibitor TargetMol T0746
    • Chemical Class:

      A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6. ChEBI CHEBI:16742, https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16742
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-N0157
      Cell Cycle/DNA Damage; MedChem Express HY-N0157
      DHOase TargetMol T0746
      DNA Damage/DNA Repair TargetMol T0746
      Nucleoside antimetabolite/analog MedChem Express HY-N0157
      Orotic acid (OA) is an intermediate in pyrimidine metabolism. MedChem Express
      Orotic acid (OA) is an intermediate in pyrimidine metabolism.; IC50 Value: ; Target: Nucleoside antimetabolite/analog; in vitro: OA increases cell proliferation and decreases apoptosis in serum-starved SK-Hep1 hepatocellular carcinoma cells, which may ascribe to the inhibition of AMP-activated protein kinase (AMPK) phosphorylation and thus activation of mammalian target of rapamycin complex 1 (mTORC1) [1].; in vivo: male Fischer 344 rats (130-150 g) to two-thirds PH in the absence or in the presence of OA (a 300-mg tablet of OA methyl ester implanted intraperitoneally at the time of two-thirds PH). MedChem Express HY-N0157
      Orotic acid (OA) is an intermediate in pyrimidine metabolism.;IC50 Value: ;Target: Nucleoside antimetabolite/analog;In vitro: OA increases cell proliferation and decreases apoptosis in serum-starved SK-Hep1 hepatocellular carcinoma cells, which may ascribe to the inhibition of AMP-activated protein kinase (AMPK) phosphorylation and thus activation of mammalian target of rapamycin complex 1 (mTORC1) [1].;In vivo: male Fischer 344 rats (130-150 g) to two-thirds PH in the absence or in the presence of OA (a 300-mg tablet of OA methyl ester implanted intraperitoneally at the time of two-thirds PH). treatment with OA resulted in a near-100% inhibition of RNR induced by two-thirds PH in rat liver, as monitored by enzyme activity and protein level [2]. The increases of hepatic OA and betaine levels in OA feeding rats was also found when compared to the normal rats [3]. Feeding 1% OA with diet decreased the phosphorylation of AMPK and increased the maturation of SREBP-1 and the expression MedChem Express HY-N0157
  • Gas Chromatography

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

Density: 1.6±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.568
Molar Refractivity: 31.1±0.3 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 1
#Rule of 5 Violations: 0
ACD/LogP: -0.93
ACD/LogD (pH 5.5): -3.83
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.75
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 96 Å2
Polarizability: 12.3±0.5 10-24cm3
Surface Tension: 68.6±3.0 dyne/cm
Molar Volume: 95.1±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) =  -0.11
    Log Kow (Exper. database match) =  -0.83
       Exper. Ref:  Sangster (1994)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  448.63  (Adapted Stein & Brown method)
    Melting Pt (deg C):  188.60  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.66E-010  (Modified Grain method)
    MP  (exp database):  334 deg C
    Subcooled liquid VP: 5.31E-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):  1.786e+004
       log Kow used: -0.83 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1820 mg/L (18 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  1700 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  75289 mg/L
    Wat Sol (Exper. database match) =  1820.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  1700.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.10E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.909E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.83  (exp database)
  Log Kaw used:  -12.480  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.650
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7459
   Biowin2 (Non-Linear Model)     :   0.8077
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.2188  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0081  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4351
   Biowin6 (MITI Non-Linear Model):   0.3063
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.9493
 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):  7.08E-005 Pa (5.31E-007 mm Hg)
  Log Koa (Koawin est  ): 11.650
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0424 
       Octanol/air (Koa) model:  0.11 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.605 
       Mackay model           :  0.772 
       Octanol/air (Koa) model:  0.898 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   8.9072 E-12 cm3/molecule-sec
      Half-Life =     1.201 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    14.410 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.689 (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: -0.83 (expkow database)

 Volatilization from Water:
    Henry LC:  8.1E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.031E+010  hours   (3.763E+009 days)
    Half-Life from Model Lake : 9.852E+011  hours   (4.105E+010 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       2.51e-005       24.4         1000       
   Water     38.9            360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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