ChemSpider 2D Image | folinic acid | C20H23N7O7

folinic acid

  • Molecular FormulaC20H23N7O7
  • Average mass473.439 Da
  • Monoisotopic mass473.165894 Da
  • ChemSpider ID5784
  • defined stereocentres - 1 of 2 defined stereocentres


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Featured data source



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

(2S)-2-[(4-{[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl)methyl]amino}benzoyl)amino]pentandisäure [German]
(2S)-2-[(4-{[(2-Amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl)methyl]amino}benzoyl)amino]pentanedioic acid
200-361-6 [EINECS]
58-05-9 [RN]
5-Formyl-5,6,7,8-tetrahydrofolic acid
5-Formyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid
5-formyltetrahydrofolic acid
Acide (2S)-2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-6-ptéridinyl)méthyl]amino}benzoyl)amino]pentanedioïque [French]
Acide N-(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydro-6-ptéridinyl)méthyl]amino}benzoyl)-L-glutamique [French] [ACD/IUPAC Name]
Citrovorum factor
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:15640 [DBID]
DivK1c_000222 [DBID]
KBio1_000222 [DBID]
KBio2_001339 [DBID]
KBio2_003907 [DBID]
KBio2_006475 [DBID]
KBio3_001438 [DBID]
KBioGR_000461 [DBID]
KBioSS_001339 [DBID]
NINDS_000222 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A formyltetrahydrofolic acid in which the formyl group is located at position 5. ChEBI CHEBI:15640
    • Bio Activity:

      Antifolate MedChem Express HY-17556
      Cell Cycle/DNA Damage MedChem Express HY-17556
      Cell Cycle/DNA Damage; MedChem Express HY-17556
      Folinic acid is an adjuvant used in cancer chemotherapy involving the drug methotrexate. MedChem Express
      Folinic acid is an adjuvant used in cancer chemotherapy involving the drug methotrexate.; Target: Antifolate; Folinic acid is a 5-formyl derivative of tetrahydrofolic acid. MedChem Express HY-17556
      Folinic acid is an adjuvant used in cancer chemotherapy involving the drug methotrexate.;Target: AntifolateFolinic acid is a 5-formyl derivative of tetrahydrofolic acid. It is readily converted to other reduced folic acid derivatives (e.g., tetrahydrofolate), and, thus, has vitamin activity that is equivalent to that of folic acid. Since it does not require the action of dihydrofolate reductase for its conversion, its function as a vitamin is unaffected by inhibition of this enzyme by drugs such as methotrexate. In 1980s, however, folinic acid was found to reactivate the dihydrofolate reductase itself even when methotrexate exists. Although the mechanism is not very clear, the polyglutamylation of methotrexate and dihydrofolate in malignant cells is considered to play an important role in the selective reactivation of dihydrofolate reductase by folinic acid in normal cells [1]. Folinic acid is generally administered along with MTX as a rescue agent to decrease MTX-induced toxicity. MedChem Express HY-17556

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

Density: 1.7±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.748
Molar Refractivity: 114.2±0.5 cm3
#H bond acceptors: 14
#H bond donors: 8
#Freely Rotating Bonds: 9
#Rule of 5 Violations: 2
ACD/LogP: -3.19
ACD/LogD (pH 5.5): -5.62
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -6.33
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 216 Å2
Polarizability: 45.3±0.5 10-24cm3
Surface Tension: 80.9±7.0 dyne/cm
Molar Volume: 280.7±7.0 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) =  -2.91

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  933.73  (Adapted Stein & Brown method)
    Melting Pt (deg C):  349.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.25E-023  (Modified Grain method)
    Subcooled liquid VP: 6.43E-020 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):  1.583e+004
       log Kow used: -2.91 (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:
       Aliphatic Amines-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   Incomplete
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.919E-028 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Can Not Estimate (can not calculate HenryLC)

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0079
   Biowin2 (Non-Linear Model)     :   0.8964
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6632  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.2816  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0426
   Biowin6 (MITI Non-Linear Model):   0.0011
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.5768
 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):  8.57E-018 Pa (6.43E-020 mm Hg)
  Log Koa (): not available
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.5E+011 
       Octanol/air (Koa) model:  not available
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  not available

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 274.0186 E-12 cm3/molecule-sec
      Half-Life =     0.039 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.104 Min
   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): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1532
      Log Koc:  3.185 

 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: -2.91 (estimated)

 Volatilization from Water:
    Henry LC:  4.92E-028 atm-m3/mole  (calculated from VP/WS)
    Half-Life from Model River:  2.59E+024  hours   (1.079E+023 days)
    Half-Life from Model Lake : 2.825E+025  hours   (1.177E+024 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       3.04e-007       0.931        1000       
   Water     46.5            900          1000       
   Soil      53.5            1.8e+003     1000       
   Sediment  0.0892          8.1e+003     0          
     Persistence Time: 973 hr




                    

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