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Search term: FTBJKONNNSKOLX-XUDSTZEEBD
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Inherent Properties, Identifiers and References
ChemSpider ID: 59638
Empirical Formula: C21H32O2
Molecular Weight: 316.4776
Nominal Mass: 316 Da
Average Mass: 316.4776 Da
Monoisotopic Mass: 316.24023 Da
Systematic Name: (8R,9S,10R,13S,14S,17S)-13,17-diethyl-17-hydroxy-1,2,6,7,8,9,10,1​1,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES: O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)CC​)CC4
InChI: InChI=1/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)​19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,​19-,20-,21-/m0/s1
InChIKey: FTBJKONNNSKOLX-XUDSTZEEBD
Std. InChI: InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17​)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+​,19-,20-,21-/m0/s1
Std. InChIKey: FTBJKONNNSKOLX-XUDSTZEESA-N
(Details...) Wikipedia Article(s)
Norbolethone (Genabol) is an anabolic steroid. It was first developed in 1966 by Wyeth Laboratories, and tested for use as an agent to encourage weight gain and for the treatment of short stature, but was never marketed commercially because of fears that it might be toxic. It subsequently showed up in urine tests on athletes in competition in the early 2000s. Norbolethone was found to have been brought to the market by the chemist Patrick Arnold, of the Bay Area Laboratory Co-operative (BALCO), an American nutritional supplement company. It is reputed to have been the active ingredient in the original formulation of the "undetectable" steroid formulation known as "The Clear" before being replaced by the more potent drug tetrahydrogestrinone. In 2002, Don Catlin, MD, the founder and then-director of the UCLA Olympic Analytical Lab and now head of the Los Angeles-based nonprofit Anti-Doping Research, identified for the first time in an athlete’s urine sample norbolethone, the first reported "designer" anabolic steroid. In the same year, U.S. bicycle racer Tammy Thomas was caught using it and was banned from her sport. Read more... or Edit at Wikipedia...
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Names and Synonyms

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(8R,9S,10​R,13S,14S​,17S)-13,​17-Diethy​l-17-hydr​oxy-1,2,6​,7,8,9,10​,11,12,13​,14,15,16​,17-tetra​decahydro​-3H-cyclo​penta[a]p​henanthre​n-3-one (​non-prefe​rred name)

18,19-Din​or-17.alp​ha.-pregn​-4-en-3-o​ne, 13-et​hyl-17-hy​droxy-

18,19-Din​orpregn-4​-en-3-one​, 13-ethy​l-17-hydr​oxy-, (17​.alpha.)-

3-Ethyl-1​7-hydroxy​-18,19-di​norpregn-​4-en-3-one

dl-13b,17​a-Diethyl​-17b-hydr​oxygon-4-​en-3-one

Gon-4-en-​3-one, 13​.beta.,17​.alpha.-d​iethyl-17​-hydroxy-

Norboleto​ne

(.+-.)-13​-Ethyl-17​-hydroxy-​18,19-din​or-17.alp​ha.-pregn​-4-en-3-o​ne

(+-)-13-E​thyl-17-h​ydroxy-18​,19-dinor​-17alpha ​-pregn-4-​en-3-one

(+-)-13-E​thyl-17-h​ydroxy-18​,19-dinor​-17alpha-​pregn-4-e​n-3-one

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(Details...) ACD/Labs Predicted Properties
ACD/LogP: 4.60 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 4.6 ACD/LogD (pH 7.4): 4.6
ACD/BCF (pH 5.5): 1844.17 ACD/BCF (pH 7.4): 1844.17
ACD/KOC (pH 5.5): 7572.83 ACD/KOC (pH 7.4): 7572.83
#H bond acceptors: 2 #H bond donors: 1
#Freely Rotating Bonds: 3 Polar Surface Area: 26.3 Å2
Index of Refraction: 1.551 Molar Refractivity: 92.37 cm3
Molar Volume: 289.4 cm3 Polarizability: 36.62 10-24cm3
Surface Tension: 43.6 dyne/cm Density: 1.09 g/cm3
Flash Point: 195.6 °C Enthalpy of Vaporization: 83.05 kJ/mol
Boiling Point: 459.5 °C at 760 mmHg Vapour Pressure: 2.24E-10 mmHg at 25°C
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.25

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.81  (Adapted Stein & Brown method)
    Melting Pt (deg C):  157.38  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.82E-009  (Modified Grain method)
    Subcooled liquid VP: 1.09E-007 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):  7.441
       log Kow used: 4.25 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.6446 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.22E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.698E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.25  (KowWin est)
  Log Kaw used:  -6.595  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.845
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2358
   Biowin2 (Non-Linear Model)     :   0.0046
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0531  (months      )
   Biowin4 (Primary Survey Model) :   3.0620  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3370
   Biowin6 (MITI Non-Linear Model):   0.0642
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2073
 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):  1.45E-005 Pa (1.09E-007 mm Hg)
  Log Koa (Koawin est  ): 10.845
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.206 
       Octanol/air (Koa) model:  0.0172 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.882 
       Mackay model           :  0.943 
       Octanol/air (Koa) model:  0.579 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 110.2765 E-12 cm3/molecule-sec
      Half-Life =     0.097 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.164 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 0.912 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  5353
      Log Koc:  3.729 

 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 = 2.574 (BCF = 374.6)
       log Kow used: 4.25 (estimated)

 Volatilization from Water:
    Henry LC:  6.22E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.675E+005  hours   (6977 days)
    Half-Life from Model Lake : 1.827E+006  hours   (7.612E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              42.58  percent
    Total biodegradation:        0.42  percent
    Total sludge adsorption:    42.16  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       0.0318          1.43         1000       
   Water     11.9            1.44e+003    1000       
   Soil      81.5            2.88e+003    1000       
   Sediment  6.55            1.3e+004     0          
     Persistence Time: 1.87e+003 hr
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 0, 0, 0, 0, 2, 0, 0, 1, 2, 30, 0, 0, 1, 0, 0, 1, 1, 2, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.88
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.42
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.41
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.28
Nuclear Hormone ReceptorsGR, glucocorticoid receptor1m2z0.10
MetalloenzymesACE, angiotensin-converting enzyme1o860.03
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.03
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.02
KinasesSRC, tyrosine kinase SRC2src0.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Serine ProteasesThrombin1ba80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Nuclear Hormone ReceptorsER, estrogen receptor; antagonist3ert0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Other EnzymesInhA, enoyl ACP reductase1p440.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
Other EnzymesNA, neuraminidase1a4g0.00
Serine ProteasesTrypsin1bju0.00
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.00
Other EnzymesGPB, glycogen phosphorylase1a8i0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.00
MetalloenzymesADA, adenosine deaminase1stw0.00
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
Other EnzymesALR2, aldose reductase1ah30.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
KinasesTK, thymidine kinase1kim0.00
Other EnzymesCOX-1, cyclooxygenase-11p4g0.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.00
KinasesHSP90, human heat shock protein 901uy60.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
KinasesEGFr, epidermal growth factor receptor1m170.00
Serine ProteasesFXa, factor Xa1f0r0.00