ChemSpider 2D Image | (−)-Riboflavin | C17H20N4O6

(−)-Riboflavin

  • Molecular FormulaC17H20N4O6
  • Average mass376.364 Da
  • Monoisotopic mass376.138275 Da
  • ChemSpider ID431981
  • defined stereocentres - 3 of 3 defined stereocentres


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(−)-Riboflavin
(-)-Riboflavin
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol
1-Deoxy-1-(4-hydroxy-7,8-dimethyl-2-oxobenzo[g]pteridin-10(2H)-yl)-D-ribitol [ACD/IUPAC Name]
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol [ACD/IUPAC Name]
1-Desoxy-1-(4-hydroxy-7,8-dimethyl-2-oxobenzo[g]pteridin-10(2H)-yl)-D-ribitol [German] [ACD/IUPAC Name]
1-Désoxy-1-(4-hydroxy-7,8-diméthyl-2-oxobenzo[g]ptéridin-10(2H)-yl)-D-ribitol [French] [ACD/IUPAC Name]
1-Desoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol [German] [ACD/IUPAC Name]
1-Désoxy-1-(7,8-diméthyl-2,4-dioxo-3,4-dihydrobenzo[g]ptéridin-10(2H)-yl)-D-ribitol [French] [ACD/IUPAC Name]
6,7-dimethyl-9-D-ribitylisoalloxazine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

E 101 [DBID]
47861_SUPELCO [DBID]
83001_FLUKA [DBID]
AIDS123039 [DBID]
AIDS-123039 [DBID]
NCGC00091288-01 [DBID]
PH7 [DBID]
Prestwick_442 [DBID]
R0508_SIAL [DBID]
R4500_SIAL [DBID]
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  • Spectroscopy
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      yellow-gold powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable, but light-sensitive. Incompatible with strong oxidizing agents,reducing agents, bases, calcium, metallic salts. May be moisture sensitive. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 > 10000 mg kg-1, IPR-RAT LD50 560 mg kg-1, SCU-RAT LD50 5000 mg kg-1, IVN-RAT LD50 50 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      None. Oxford University Chemical Safety Data (No longer updated) More details
    • Chemical Class:

      <stereo>D</stereo>-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[<ital>g</ital>]pteridin-10(2<element>H</element>)-yl moiety. It is a nut ritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, an d in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide. ChEBI CHEBI:17015
    • Bio Activity:

      Others MedChem Express HY-B0456
      Riboflavin is an easily absorbed micronutrient with a key role in maintaining health in humans and other animals. MedChem Express
      Riboflavin is an easily absorbed micronutrient with a key role in maintaining health in humans and other animals.; Target: Others; Riboflavin (vitamin B2) is the direct precursor of redox enzyme cofactors flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), which are essential for multiple cell physiology [1]. MedChem Express HY-B0456
      Riboflavin is an easily absorbed micronutrient with a key role in maintaining health in humans and other animals.;Target: Riboflavin (vitamin B2) is the direct precursor of redox enzyme cofactors flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), which are essential for multiple cell physiology [1]. Urinary excretion of riboflavin contributes to one-half of the overall removal of riboflavin from plasma. No sex differences were observed for any of the pharmacokinetic variables (P > 0.05) [2]. Riboflavin, similar to other vitamins of the B complex, presents anti-inflammatory activity but its full characterization has not yet been carried out. Riboflavin (25, 50 or 100 mg/kg, i.p.), administered immediately and 2 h after the injection of carrageenan, induced antiedema and antinociceptive effects. The antinociceptive effect was not inhibited by the pretreatment with cadmium sulfate (1 mg/kg), an inhibitor of flavokinase. Riboflavin (50 or 100 mg/kg, i.p., 0 and 2 MedChem Express HY-B0456

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: 1.733
Molar Refractivity: 91.1±0.5 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 2
ACD/LogP: -2.02
ACD/LogD (pH 5.5): -1.14
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 5.72
ACD/LogD (pH 7.4): -1.14
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.70
Polar Surface Area: 155 Å2
Polarizability: 36.1±0.5 10-24cm3
Surface Tension: 70.3±7.0 dyne/cm
Molar Volume: 227.5±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) =  -1.05
    Log Kow (Exper. database match) =  -1.46
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  709.77  (Adapted Stein & Brown method)
    Melting Pt (deg C):  310.59  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.17E-021  (Modified Grain method)
    MP  (exp database):  280 dec deg C
    Subcooled liquid VP: 1.43E-018 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):  3702
       log Kow used: -1.46 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  84.7 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.6683e+005 mg/L
    Wat Sol (Exper. database match) =  84.70
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.59E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.903E-025 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.46  (exp database)
  Log Kaw used:  -16.833  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.373
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3126
   Biowin2 (Non-Linear Model)     :   0.9641
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8576  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6855  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2832
   Biowin6 (MITI Non-Linear Model):   0.0517
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0128
 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):  1.91E-016 Pa (1.43E-018 mm Hg)
  Log Koa (Koawin est  ): 15.373
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.57E+010 
       Octanol/air (Koa) model:  579 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 247.3547 E-12 cm3/molecule-sec
      Half-Life =     0.043 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.519 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  325.8
      Log Koc:  2.513 

 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: -1.46 (expkow database)

 Volatilization from Water:
    Henry LC:  3.59E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.164E+015  hours   (1.318E+014 days)
    Half-Life from Model Lake : 3.452E+016  hours   (1.438E+015 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       0.127           1.04         1000       
   Water     46.5            360          1000       
   Soil      53.3            720          1000       
   Sediment  0.085           3.24e+003    0          
     Persistence Time: 366 hr




                    

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