ChemSpider 2D Image | calanolide A | C22H26O5

calanolide A

  • Molecular FormulaC22H26O5
  • Average mass370.439 Da
  • Monoisotopic mass370.178009 Da
  • ChemSpider ID58497
  • defined stereocentres - 3 of 3 defined stereocentres


More details:






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

(+)-(10R,11S��12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-11��12-dihydro-2H��6H,10H-benzo(1��2-b��3,4-b'��5,6-b"]tripyran-2-one
(10R-(10a,11b,12a))-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one
(10R,11S,12S)-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
(10R,11S,12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-on [German] [ACD/IUPAC Name]
(10R,11S,12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one [ACD/IUPAC Name]
(10R,11S,12S)-12-Hydroxy-6,6,10,11-tétraméthyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromén-2-one [French] [ACD/IUPAC Name]
142632-32-4 [RN]
2H,6H,10H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one, 11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-, (10R,11S,12S)- [ACD/Index Name]
calanolide A
(+)-(10R,11S,12S)-10,11-trans-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0308 [DBID]
S5A9TQN46W [DBID]
AIDS004462 [DBID]
AIDS-004462 [DBID]
AIDS032546 [DBID]
AIDS-032546 [DBID]
C09147 [DBID]
DRG-0308 [DBID]
NSC 650886 [DBID]
NSC 675451 [DBID]
More...
  • Miscellaneous
    • Chemical Class:

      An organic heterotetracyclic compound that is 11,12-dihydro-2<element>H</element>,6<element>H</element>,10<element>H</element>-dipyrano[2,3-<ital>f</ital>:2',3'-<ital>h</ital>]chromen-2-one substitute d by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10<stereo>R</stereo>,11<stereo>S</stereo>,12<stereo>S</stereo> stereoisomer). Isol ated from <ital>Calophyllum lanigerum</ital> var <ital>austrocoriaceum</ital> and <ital>Calophyllum brasiliense</ital>, it exhibits potent activity against HIV-1 reverse transcriptase. ChEBI CHEBI:65552

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

Density: 1.2±0.1 g/cm3
Boiling Point: 514.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 82.8±3.0 kJ/mol
Flash Point: 177.2±23.6 °C
Index of Refraction: 1.559
Molar Refractivity: 101.2±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 5.03
ACD/LogD (pH 5.5): 4.70
ACD/BCF (pH 5.5): 2210.78
ACD/KOC (pH 5.5): 8622.28
ACD/LogD (pH 7.4): 4.70
ACD/BCF (pH 7.4): 2210.78
ACD/KOC (pH 7.4): 8622.27
Polar Surface Area: 65 Å2
Polarizability: 40.1±0.5 10-24cm3
Surface Tension: 40.7±3.0 dyne/cm
Molar Volume: 313.6±3.0 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) =  5.01

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  511.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  218.16  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.02E-013  (Modified Grain method)
    Subcooled liquid VP: 8.08E-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):  0.7945
       log Kow used: 5.01 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.17013 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.32E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.307E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.01  (KowWin est)
  Log Kaw used:  -10.268  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.278
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9840
   Biowin2 (Non-Linear Model)     :   0.9967
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3523  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6725  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7076
   Biowin6 (MITI Non-Linear Model):   0.3478
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.7080
 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):  1.08E-008 Pa (8.08E-011 mm Hg)
  Log Koa (Koawin est  ): 15.278
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  278 
       Octanol/air (Koa) model:  466 
   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 = 316.5490 E-12 cm3/molecule-sec
      Half-Life =     0.034 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.328 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    15.750000 E-17 cm3/molecule-sec
      Half-Life =     0.073 Days (at 7E11 mol/cm3)
      Half-Life =      1.746 Hrs
   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    :  1898
      Log Koc:  3.278 

 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 = 3.157 (BCF = 1436)
       log Kow used: 5.01 (estimated)

 Volatilization from Water:
    Henry LC:  1.32E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 8.537E+008  hours   (3.557E+007 days)
    Half-Life from Model Lake : 9.313E+009  hours   (3.88E+008 days)

 Removal In Wastewater Treatment:
    Total removal:              78.02  percent
    Total biodegradation:        0.68  percent
    Total sludge adsorption:    77.34  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       0.0157          0.554        1000       
   Water     11.1            900          1000       
   Soil      62.9            1.8e+003     1000       
   Sediment  26              8.1e+003     0          
     Persistence Time: 1.5e+003 hr




                    

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