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Search term: VXIMPSPISRVBPZ-NWUMPJBXBM
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Inherent Properties, Identifiers and References
ChemSpider ID: 18023
Empirical Formula: C22H30O3
Molecular Weight: 342.4718
Nominal Mass: 342 Da
Average Mass: 342.4718 Da
Monoisotopic Mass: 342.219495 Da
Systematic Name: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,​8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one
SMILES: O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](O)(C(=O)C)CC[C@@H]12)C​)[C@@]3(C)CC4)C
InChI: InChI=1/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21​(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-​,17+,18+,20-,21+,22+/m1/s1
InChIKey: VXIMPSPISRVBPZ-NWUMPJBXBM
Std. InChI: InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-2​1(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16​-,17+,18+,20-,21+,22+/m1/s1
Std. InChIKey: VXIMPSPISRVBPZ-NWUMPJBXSA-N
(Details...) Wikipedia Article(s)
Megestrol is a progesterone derivative with antineoplastic properties used in the treatment of advanced carcinoma of the breast and endometrium. When given in relatively high doses, Megestrol can substantially increase appetite in most individuals, even those with advanced cancer. It is also used to boost appetite in individuals with other cancers or HIV/AIDS. Megestrol acetate oral suspension (a form of Megestrol) is used primarily as an appetite enhancer. The method of appetite enhancement is not known, but it can cause high blood sugar. Currently, it is manufactured under the trade name Megace. Little is known about the drug's chemical interactions. Doses range from 40 mg three times a day, 30 minutes before meals, to 800 mg once a day. Side effects may include diarrhea, rash, and impotence. Males may have some feminizing effects such as gynecomastia (breast development). It is a category X U.S. Food and Drug Administration drug, which means cannot be used in pregnancy as it crosses the placenta and malignantly affects the fetus. It may cause adrenal insufficiency. Read more... or Edit at Wikipedia...
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Names and Synonyms

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222-628-6 [EINECS/ELINCS]

3562-63-8 [RN]

megestrol [Wiki]

Megestrol​o [DCIT]

megestrol​um [Latin]

Pregna-4,​6-diene-3​,20-dione​, 17-hydr​oxy-6-met​hyl-

DMAP

17-Hydrox​y-6-methy​lpregna-4​,6-diene-​3,20-dione

9005-80-5 [RN]

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Database ID(s)

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(Details...) ACD/Labs Predicted Properties
ACD/LogP: 3.06 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 3.06 ACD/LogD (pH 7.4): 3.06
ACD/BCF (pH 5.5): 124.95 ACD/BCF (pH 7.4): 124.95
ACD/KOC (pH 5.5): 1102.7 ACD/KOC (pH 7.4): 1102.69
#H bond acceptors: 3 #H bond donors: 1
#Freely Rotating Bonds: 2 Polar Surface Area: 43.37 Å2
Index of Refraction: 1.569 Molar Refractivity: 96.83 cm3
Molar Volume: 295.4 cm3 Polarizability: 38.38 10-24cm3
Surface Tension: 46.4 dyne/cm Density: 1.15 g/cm3
Flash Point: 270.5 °C Enthalpy of Vaporization: 88.55 kJ/mol
Boiling Point: 500.4 °C at 760 mmHg Vapour Pressure: 4.15E-12 mmHg at 25°C
MeSH
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.41

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  436.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  182.93  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.48E-010  (Modified Grain method)
    Subcooled liquid VP: 1.54E-008 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):  27.02
       log Kow used: 3.41 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5.9991 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 :   1.14E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.804E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.41  (KowWin est)
  Log Kaw used:  -6.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.742
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0464
   Biowin2 (Non-Linear Model)     :   0.0004
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7610  (months      )
   Biowin4 (Primary Survey Model) :   2.8489  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3013
   Biowin6 (MITI Non-Linear Model):   0.0345
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.0175
 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):  2.05E-006 Pa (1.54E-008 mm Hg)
  Log Koa (Koawin est  ): 9.742
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.46 
       Octanol/air (Koa) model:  0.00136 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.981 
       Mackay model           :  0.992 
       Octanol/air (Koa) model:  0.0978 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 255.5080 E-12 cm3/molecule-sec
      Half-Life =     0.042 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.502 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    34.222500 E-17 cm3/molecule-sec
      Half-Life =     0.033 Days (at 7E11 mol/cm3)
      Half-Life =     48.221 Min
   Fraction sorbed to airborne particulates (phi): 0.986 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  622.2
      Log Koc:  2.794 

 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 = 1.929 (BCF = 84.91)
       log Kow used: 3.41 (estimated)

 Volatilization from Water:
    Henry LC:  1.14E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.505E+004  hours   (3960 days)
    Half-Life from Model Lake : 1.037E+006  hours   (4.321E+004 days)

 Removal In Wastewater Treatment:
    Total removal:              11.14  percent
    Total biodegradation:        0.17  percent
    Total sludge adsorption:    10.97  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       0.0131          0.447        1000       
   Water     14.6            1.44e+003    1000       
   Soil      84.4            2.88e+003    1000       
   Sediment  1               1.3e+004     0          
     Persistence Time: 1.6e+003 hr
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 0, 0, 0, 0, 0, 4, 0, 0, 1, 2, 27, 0, 0, 2, 0, 0, 2, 2, 4, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.88
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.42
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.40
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.24
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
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.02
KinasesSRC, tyrosine kinase SRC2src0.01
Serine ProteasesThrombin1ba80.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
KinasesHSP90, human heat shock protein 901uy60.00
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
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
KinasesTK, thymidine kinase1kim0.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
Serine ProteasesFXa, factor Xa1f0r0.00
MetalloenzymesADA, adenosine deaminase1stw0.00
KinasesEGFr, epidermal growth factor receptor1m170.00