ChemSpider 2D Image | Griseofulvin | C17H17ClO6

Griseofulvin

  • Molecular FormulaC17H17ClO6
  • Average mass352.766 Da
  • Monoisotopic mass352.071381 Da
  • ChemSpider ID389934

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(+)-Griseofulvin
(1'S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
(2S)-trans-7-Chloro-2',4,6-trimethoxy-6'-methylspiro(benzofuran-2[3H],1'-[2]cyclohexene)-3,4'-dione
(2S,6'R)-7-Chlor-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]en]-3,4'-dion [German]
(2S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione [ACD/IUPAC Name]
(2S,6'R)-7-Chloro-2',4,6-triméthoxy-6'-méthyl-3H,4'H-spiro[1-benzofurane-2,1'-cyclohex[2]ène]-3,4'-dione [French]
126-07-8 [RN]
204-767-4 [EINECS]
2884-22-2 [RN]
95226 [Beilstein]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

32HRV3E3D5 [DBID]
875 [DBID]
UNII-32HRV3E3D5 [DBID]
46309_RIEDEL [DBID]
AI3-51015 [DBID]
AIDS007959 [DBID]
AIDS-007959 [DBID]
BRN 0095226 [DBID]
C06686 [DBID]
Caswell No. 471B [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Organochloride; Ether; Ester; Drug; Anti-Bacterial Agent; Antifungal Agent; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D4696

    • Safety:

      53-45 Alfa Aesar B23521
      61-40-43 Alfa Aesar B23521
      D01AA08 Wikidata Q416096
      D01BA01 Wikidata Q416096
      WARNING: Irreversible damage risk, protect skin/eyes/lungs. Alfa Aesar B23521

    • Chemical Class:

      An oxaspiro compound produced by <ital>Penicillium griseofulvum</ital>. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topica l treatment. ChEBI CHEBI:27779
      An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topica; l treatment . ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27779
      An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment. ChEBI CHEBI:27779

    • Therapeutical Effect:

      antifungal, inhibits mitosis in metaphase Rudolf Boehm Institute [00200046]

    • Compound Source:

      Isolated from a microorganism Susan Richardson [Structure found on ChemSpider, confirmed from ACD/Dictionary, DOI: 10.1590/S0100-40422005000600011 and The Merck Index Online]
      Penicillium griseofulvum Rudolf Boehm Institute [00200046]
      Xylaria sp. (Xylariaceae) Susan Richardson [Structure found on ChemSpider, confirmed from ACD/Dictionary, DOI: 10.1590/S0100-40422005000600011 and The Merck Index Online]

    • Bio Activity:

      Antifungal MedChem Express HY-17583
      Anti-infection MedChem Express HY-17583
      Anti-infection; MedChem Express HY-17583
      Griseofulvin(Gris-PEG; Grifulvin) is a spirocyclic fungal natural product used in treatment of fungal dermatophytes; Antifungal drug. MedChem Express http://www.medchemexpress.com/desoximetasone.html, HY-17583

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 570.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 85.6±3.0 kJ/mol
Flash Point: 228.0±29.1 °C
Index of Refraction: 1.583
Molar Refractivity: 85.3±0.4 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 3.53
ACD/LogD (pH 5.5): 2.88
ACD/BCF (pH 5.5): 91.29
ACD/KOC (pH 5.5): 880.80
ACD/LogD (pH 7.4): 2.88
ACD/BCF (pH 7.4): 91.29
ACD/KOC (pH 7.4): 880.80
Polar Surface Area: 71 Å2
Polarizability: 33.8±0.5 10-24cm3
Surface Tension: 52.6±5.0 dyne/cm
Molar Volume: 255.1±5.0 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) =  -0.31

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  441.97  (Adapted Stein & Brown method)
    Melting Pt (deg C):  185.49  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.35E-008  (Modified Grain method)
    Subcooled liquid VP: 2.06E-006 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):  1.095e+004
       log Kow used: -0.31 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  77711 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.13E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.844E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.31  (KowWin est)
  Log Kaw used:  -10.335  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.025
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.0915
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.9546  (months      )
   Biowin4 (Primary Survey Model) :   3.0013  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0189
   Biowin6 (MITI Non-Linear Model):   0.0016
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8715
 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):  0.000275 Pa (2.06E-006 mm Hg)
  Log Koa (Koawin est  ): 10.025
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0109 
       Octanol/air (Koa) model:  0.0026 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.283 
       Mackay model           :  0.466 
       Octanol/air (Koa) model:  0.172 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 278.4503 E-12 cm3/molecule-sec
      Half-Life =     0.038 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.657 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     8.699800 E-17 cm3/molecule-sec
      Half-Life =     0.132 Days (at 7E11 mol/cm3)
      Half-Life =      3.161 Hrs
   Fraction sorbed to airborne particulates (phi): 0.375 (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: -0.31 (estimated)

 Volatilization from Water:
    Henry LC:  1.13E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.732E+008  hours   (4.055E+007 days)
    Half-Life from Model Lake : 1.062E+010  hours   (4.423E+008 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       2.01e-005       0.714        1000       
   Water     49.1            1.44e+003    1000       
   Soil      50.8            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.18e+003 hr

Click to predict properties on the Chemicalize site


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