ChemSpider 2D Image | Cholecalciferol | C27H44O

Cholecalciferol

  • Molecular FormulaC27H44O
  • Average mass384.638 Da
  • Monoisotopic mass384.339203 Da
  • ChemSpider ID4444353

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

Cholecalciferol [BAN] [USAN] [Wiki]
(+)-vitamin D3
(1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]-7a-methyloctahydro-4H-inden-4-yliden}ethyliden]-4-methylidencyclohexanol
(1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexanol
(1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(1R)-1,5-diméthylhexyl]-7a-méthyloctahydro-4H-indén-4-ylidène}éthylidène]-4-méthylidènecyclohexanol [French]
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
(1S,3Z)-4-Methylene-3-[(2E)-2-{(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methyl-2-heptanyl]octahydro-4H-inden-4-ylidene}ethylidene]cyclohexanol
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-trien-3-ol [ACD/IUPAC Name]
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-trien-3-ol [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1497 [DBID]
47763_SUPELCO [DBID]
89193_FLUKA [DBID]
bmse000507 [DBID]
C05443 [DBID]
C1357_SIAL [DBID]
C9756_SIGMA [DBID]
C9774_SIAL [DBID]
CCRIS 5813 [DBID]
CCRIS 6286 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Organic Compound; Drug; Essential Vitamin; Food Toxin; Antihypocalcemic Agent; Bone Density Conservation Agent; Vitamin; Antihypoparathyroid Agent; Vitamin D; Metabolite; Nutraceutical; Household Toxin; Synthetic Compound; Antithyroid Agent Toxin, Toxin-Target Database T3D2703

    • Safety:

      A11CC05 Wikidata Q139347

    • Chemical Class:

      A hydroxy seco-steroid that is (5<stereo>Z</stereo>,7<stereo>E</stereo>)-9,10-secocholesta-5,7,10(19)-triene in which the <ital>pro</ital>-<stereo>S</stereo> hydrogen at position 3 has been replaced b y a hydroxy group. It is the inactive form of vitamin D<smallsub>3</smallsub>, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D<smallsub>3</smallsub>), which is then further hydroxyla ted in the kidney to give calcitriol (1,25-dihydroxyvitamin D<smallsub>3</smallsub>), the active hormone. ChEBI CHEBI:28940
      A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced b; y a hydroxy group. It is the inactive form of vitamin D3, bein g hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxyla; ted in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28940

    • Bio Activity:

      Nuclear Receptors Tocris Bioscience 4156
      Precursor of calcifediol (Cat. No. 4036). Naturally occurring form of vitamin D Tocris Bioscience 4156
      Precursor of calcifediol (Cat. No. 4036). Naturally occurring form of vitamin D; predominantly active form found in humans. Tocris Bioscience 4156
      Vitamin D Receptors Tocris Bioscience 4156

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

Density: 1.0±0.1 g/cm3
Boiling Point: 496.4±24.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.9 mmHg at 25°C
Enthalpy of Vaporization: 88.0±6.0 kJ/mol
Flash Point: 214.2±15.1 °C
Index of Refraction: 1.523
Molar Refractivity: 121.3±0.4 cm3
#H bond acceptors: 1
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 9.72
ACD/LogD (pH 5.5): 8.65
ACD/BCF (pH 5.5): 1000000.00
ACD/KOC (pH 5.5): 1216243.50
ACD/LogD (pH 7.4): 8.65
ACD/BCF (pH 7.4): 1000000.00
ACD/KOC (pH 7.4): 1216243.50
Polar Surface Area: 20 Å2
Polarizability: 48.1±0.5 10-24cm3
Surface Tension: 37.1±5.0 dyne/cm
Molar Volume: 396.9±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) =  10.24

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  444.39  (Adapted Stein & Brown method)
    Melting Pt (deg C):  168.98  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.41E-009  (Modified Grain method)
    MP  (exp database):  84.5 deg C
    Subcooled liquid VP: 8.96E-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):  2.224e-005
       log Kow used: 10.24 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.00023488 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.30E-004  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.484E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  10.24  (KowWin est)
  Log Kaw used:  -2.027  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.267
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5392
   Biowin2 (Non-Linear Model)     :   0.0448
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2970  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2688  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0650
   Biowin6 (MITI Non-Linear Model):   0.0122
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0733
 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):  1.19E-006 Pa (8.96E-009 mm Hg)
  Log Koa (Koawin est  ): 12.267
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.51 
       Octanol/air (Koa) model:  0.454 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.989 
       Mackay model           :  0.995 
       Octanol/air (Koa) model:  0.973 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 269.6903 E-12 cm3/molecule-sec
      Half-Life =     0.040 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.555 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    41.616249 E-17 cm3/molecule-sec
      Half-Life =     0.028 Days (at 7E11 mol/cm3)
      Half-Life =     39.654 Min
   Fraction sorbed to airborne particulates (phi): 0.992 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.515E+006
      Log Koc:  6.180 

 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: 10.24 (estimated)

 Volatilization from Water:
    Henry LC:  0.00023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      6.994  hours
    Half-Life from Model Lake :      240.7  hours   (10.03 days)

 Removal In Wastewater Treatment:
    Total removal:              94.04  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.26  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       0.00591         0.39         1000       
   Water     1.9             900          1000       
   Soil      28.2            1.8e+003     1000       
   Sediment  69.9            8.1e+003     0          
     Persistence Time: 3.11e+003 hr

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