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- 2 of 2 defined stereocentres

cis-iso-Humulone

ChemSpider ID: 10218444
Molecular Formula: C₂₁H₃₀O₅
Average mass: 362.4599 Da
Monoisotopic mass: 362.20932 Da
Systematic name

(4R,5S)-3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-buten-1-yl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-one
SMILES and InChIs

SMILES:

C\C(C)=C\C[C@@H]1C(=O)\C(=C(\O)[C@@]1(O)C(=O)C\C=C(/C)C)C(=O)CC(C)C Copied

Std. InChI:

InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3/t15-,21+/m1/s1 Copied

Std. InChIKey:

QARXXMMQVDCYGZ-VFNWGFHPSA-N Copied
Cite this record
CSID:10218444, http://www.chemspider.com/Chemical-Structure.10218444.html (accessed 19:35, May 21, 2013) Copied

Names and Identifiers

ChemSpider Searches

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	6.029	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	3.29	ACD/LogD (pH 7.4):	2.56
ACD/BCF (pH 5.5):	41.31	ACD/BCF (pH 7.4):	7.54
ACD/KOC (pH 5.5):	83.31	ACD/KOC (pH 7.4):	15.21
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	10	Polar Surface Area:	91.67 Å²
Index of Refraction:	1.537	Molar Refractivity:	99.697 cm³
Molar Volume:	319.244 cm³	Polarizability:	39.523 10^-24cm³
Surface Tension:	45.9949989318848 dyne/cm	Density:	1.135 g/cm³
Flash Point:	288.711 °C	Enthalpy of Vaporization:	92.692 kJ/mol
Boiling Point:	530.5 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.49

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  498.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  211.10  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.16E-013  (Modified Grain method)
    Subcooled liquid VP: 6.79E-011 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):  17.45
       log Kow used: 3.49 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.0751 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.52E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.957E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.49  (KowWin est)
  Log Kaw used:  -9.512  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.002
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5703
   Biowin2 (Non-Linear Model)     :   0.0163
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2786  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2341  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3406
   Biowin6 (MITI Non-Linear Model):   0.0572
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2140
 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):  9.05E-009 Pa (6.79E-011 mm Hg)
  Log Koa (Koawin est  ): 13.002
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  331 
       Octanol/air (Koa) model:  2.47 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.995 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 281.2962 E-12 cm3/molecule-sec
      Half-Life =     0.038 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    27.377 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    86.175003 E-17 cm3/molecule-sec
      Half-Life =     0.013 Days (at 7E11 mol/cm3)
      Half-Life =     19.150 Min
   Reaction With Nitrate Radicals May Be Important!
   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    :  26.84
      Log Koc:  1.429 

 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 = 1.991 (BCF = 97.97)
       log Kow used: 3.49 (estimated)

 Volatilization from Water:
    Henry LC:  7.52E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.482E+008  hours   (6.176E+006 days)
    Half-Life from Model Lake : 1.617E+009  hours   (6.738E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              12.81  percent
    Total biodegradation:        0.18  percent
    Total sludge adsorption:    12.62  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       0.0105          0.236        1000       
   Water     18              900          1000       
   Soil      80.7            1.8e+003     1000       
   Sediment  1.27            8.1e+003     0          
     Persistence Time: 1.07e+003 hr