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Search term: ACGUYXCXAPNIKK-UHFFFAOYAL
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Inherent Properties, Identifiers and References
ChemSpider ID: 3472
Empirical Formula: C13H6Cl6O2
Molecular Weight: 406.9035
Nominal Mass: 404 Da
Average Mass: 406.9035 Da
Monoisotopic Mass: 403.849896 Da
Systematic Name: 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxy-phenyl)methyl]pheno​l
SMILES: Clc1c(c(O)c(Cl)cc1Cl)Cc2c(O)c(Cl)cc(Cl)c2Cl
InChI: InChI=1/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-​9(17)13(5)21/h2-3,20-21H,1H2
InChIKey: ACGUYXCXAPNIKK-UHFFFAOYAL
Std. InChI: InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3​-9(17)13(5)21/h2-3,20-21H,1H2
Std. InChIKey: ACGUYXCXAPNIKK-UHFFFAOYSA-N
(Details...) Wikipedia Article(s)
Hexachlorophene, also known as Nabac, is a disinfectant. The compound occurs as a white to light-tan crystalline powder, which either is odorless or produces a slightly phenolic odor. In medicine, hexachlorophene is very useful as a topical anti-infective, anti-bacterial agent, often used in soaps and toothpaste. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide. Hexachlorophene can be lethal from percutaneous (through the skin) absorption. Children may be specifically susceptible. Hexachlorophene (6.3%) was added to “baby powder” in France due to a manufacturing error. It caused encephalopathy and ulcerative skin lesions. 36 of 204 exposed children died within a few days of exposure. Two companies manufactured over-the-counter preparations. One, by The Mennen Company, Morristown, NJ, was known as Baby Magic Bath. However, Mennen recalled the product, and all bottles were taken off retail shelves. Right after the withdrawal, there was an outbreak of Staphylococcus infections in hospitals across the USA. A commercial preparation of the drug, pHisoHex, was widely used as a very effective antibacterial skin cleanser in the treatment of acne. In the U.S. during the 1960s, it was available over the counter, and remains available as a prescription body wash. In the E.U. during the 1970s and 1980s, it was available over the counter. A related product, pHisoAc, was used as a skin mask to dry and peel away acne lesions. Another preparation, pHiso-Scrub, was a hexachlorophene-impregnated sponge for scrubbing; it has since been discontinued. In 1969, hexachlorophene became suspected of causing cancer. Around 1973 it was withdrawn from over-the-counter sales as a treatment for acne, and became a prescription drug. It was later determined not to cause cancer. Nevertheless, hexachlorophene soap is not available over the counter today, because once a product has been withdrawn by the FDA it is virtually impossible for it to be reinstated, even after invalidation of the reasons for its removal. The MSDS still lists this compound as an experimental teratogen. Possibly because of the previous questions concerning its effects, most dermatologists today do not prescribe it for acne treatment. In Australia, it remains freely available from all pharmacies and supermarkets without prescription. Several substitute products (including triclosan) were developed, but none had the germ-killing capability of hexachlorophene. Read more... or Edit at Wikipedia...
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User Data

  • experimental physchem properties
    • Melting Point: 161 - 167 C
  • miscellaneous
    • Appearance: white powder
    • Stability: Stable. Incompatible with alkalies, akaline earths, tweens, strong oxidizers.
    • Toxicity: ORL-RAT LD50 60 mg kg-1, IPR-RAT LD50 22 mg kg-1, ORL-MUS LD50 67 mg kg-1
    • Safety: Safety glasses. Do not breathe dust.
    • Source: synthetic
Names and Synonyms

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

2,2'-Meth​andiylbis​(3,4,6-tr​ichlorben​zolol)

2,2'-meth​anediylbi​s(3,4,6-t​richlorop​henol)

2,2'-méth​anediylbi​s(3,4,6-t​richlorop​hénol)

2,2'-Meth​ylenebis(​3,4,6-tri​chlorophe​nol)

Compound ​G 11

German-Me​dica

Hexachlor​ophene (U​SP)

phenol, 2​,2'-methy​lenebis[3​,4,6-tric​hloro-

trichloro​phene

Fascol

More...
Database ID(s)

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

(Details...) ACD/Labs Predicted Properties
ACD/LogP: 7.20 # of Rule of 5 Violations: 1
ACD/LogD (pH 5.5): 7.15 ACD/LogD (pH 7.4): 5.84
ACD/BCF (pH 5.5): 157497.88 ACD/BCF (pH 7.4): 7678.9
ACD/KOC (pH 5.5): 177599.06 ACD/KOC (pH 7.4): 8658.94
#H bond acceptors: 2 #H bond donors: 2
#Freely Rotating Bonds: 4 Polar Surface Area: 18.46 Å2
Index of Refraction: 1.67 Molar Refractivity: 88.7 cm3
Molar Volume: 237.3 cm3 Polarizability: 35.16 10-24cm3
Surface Tension: 61 dyne/cm Density: 1.713 g/cm3
Flash Point: 238.6 °C Enthalpy of Vaporization: 76.16 kJ/mol
Boiling Point: 470.9 °C at 760 mmHg Vapour Pressure: 1.72E-09 mmHg at 25°C
MeSH
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  6.92
    Log Kow (Exper. database match) =  7.54
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  464.09  (Adapted Stein & Brown method)
    Melting Pt (deg C):  195.82  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.31E-011  (Modified Grain method)
    MP  (exp database):  166.5 deg C
    BP  (exp database):  479 deg C
    Subcooled liquid VP: 2.39E-009 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):  0.003837
       log Kow used: 7.54 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  140 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.088575 mg/L
    Wat Sol (Exper. database match) =  140.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.60E-013  atm-m3/mole
   Group Method:   5.48E-013  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.160E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  7.54  (exp database)
  Log Kaw used:  -10.454  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.994
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.2544
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.0983  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.2795  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3722
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7288
 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):  3.19E-007 Pa (2.39E-009 mm Hg)
  Log Koa (Koawin est  ): 17.994
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.41 
       Octanol/air (Koa) model:  2.42E+005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   2.1779 E-12 cm3/molecule-sec
      Half-Life =     4.911 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    58.935 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.305E+005
      Log Koc:  5.800 

 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 = 3.670 (BCF = 4680)
       log Kow used: 7.54 (expkow database)

 Volatilization from Water:
    Henry LC:  5.48E-013 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 2.155E+009  hours   (8.98E+007 days)
    Half-Life from Model Lake : 2.351E+010  hours   (9.796E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              93.98  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.20  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       0.000111        118          1000       
   Water     0.607           4.32e+003    1000       
   Soil      52.9            8.64e+003    1000       
   Sediment  46.5            3.89e+004    0          
     Persistence Time: 1.49e+004 hr
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 2, 4, 2, 2, 0, 0, 12, 0, 0, 0, 0, 18, 0, 0
CategoryTargetPDB CodeLASSO Score
Other EnzymesCOX-2, cyclooxygenase-21cx20.58
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.38
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.35
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.24
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.04
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.04
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.03
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.03
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.03
KinasesSRC, tyrosine kinase SRC2src0.03
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.02
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.02
KinasesP38 MAP, P38 mitogen activated protein1kv20.02
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.02
KinasesHSP90, human heat shock protein 901uy60.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
KinasesEGFr, epidermal growth factor receptor1m170.01
Other EnzymesGPB, glycogen phosphorylase1a8i0.01
Other EnzymesCOX-1, cyclooxygenase-11p4g0.01
Nuclear Hormone ReceptorsER, estrogen receptor; antagonist3ert0.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesInhA, enoyl ACP reductase1p440.00
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.00
Other EnzymesALR2, aldose reductase1ah30.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
MetalloenzymesACE, angiotensin-converting enzyme1o860.00
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.00
Other EnzymesHIVPR, HIV protease1hpx0.00
KinasesTK, thymidine kinase1kim0.00
Other EnzymesNA, neuraminidase1a4g0.00
Serine ProteasesFXa, factor Xa1f0r0.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
MetalloenzymesADA, adenosine deaminase1stw0.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
Serine ProteasesThrombin1ba80.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
Other EnzymesAChE, acetylcholinesterase1eve0.00