InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1

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Inherent Properties, Identifiers and References

ChemSpider ID:	5541
Empirical Formula:	C₂₂H₂₉FO₅
Molecular Weight:	392.4611
Nominal Mass:	392 Da
Average Mass:	392.4611 Da
Monoisotopic Mass:	392.199902 Da

Systematic Name:

(11beta,16alpha)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

SMILES:

O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3C)C)C Copy

InChI:

InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 Copy

InChIKey:

UREBDLICKHMUKA-CXSFZGCWBM

Std. InChI:

InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 Copy

Std. InChIKey:

UREBDLICKHMUKA-CXSFZGCWSA-N

LicenseWikipedia Article(s)

Patents

Articles

Tapan Sanghvi, Nina Ni, Michael Mayersohn, Samuel H. Yalkowsky. Predicting Passive Intestinal Absorption Using A Single Parameter , QSAR Comb. Sci. 2003, 22(2), 247-257

131 compounds and their 'Fraction Absorbed' values have been obtained from the table given in the paper. Some compounds had multiple values reported (as obtained from various references). These have been averaged and provided by us in the SDF and AMP files. The "Sanghvi_values.txt" file contains all data (as reported in Table 1) and "Sanghvi_avg_values.txt" contains averaged data for compounds with multiple entries (as reported in Table 2). "Benserazide, HCl" was retrieved as "Benserazide", "Ceftriaxone, Na" as "Ceftriaxone", "Foscarnet, Na" as "Foscarnet", "L-Dopa" as "Levodopa", "L-Leucine" as "Leucine" and "Triacrilast" as "Tiacrilast". The last compound was found to be mispelt as checked from the original reference.

QSAR World - Datasets - Sanghvi

Matthew D. Wessel, Peter C. Jurs, John W. Tolan, and Steven M. Muskal. Prediction of Human Intestinal Absorption of Drug Compounds from Molecular Structure , J. Chem. Inf. Comput. Sci., 1998, 38(4), 726-735

A total of 86 drugs and their %HIA (Human Intestinal Absorption) values taken from the table given in the paper. Compound "trovoflaxicin" was retrieved as "trovafloxacin", "acetylsalicylic acid" as "aspirin", and "phenoxymethylpenicillinic acid" as "penicillinv" from ChemIDplus. Fragment removed from "timolol maleate" during "wash". AMP file has a "Label" column indicating 9 compounds used as a "Cross-Validation Set" and 10 compounds used as an "External Prediction Set" by the authors. Rest of the compounds are labeled as "Training Set".

QSAR World - Datasets - Wessel

Jennifer D. Irvine, Lori Takahashi, Karen Lockhart, Jonathan Cheong, John W. Tolan, H. E. Selick, and J. Russell Grove. MDCK (Madin-Darby Canine Kidney) Cells: a Tool for Membrane Permeability Screening , J. Pharm. Sci. 2000, 88(1), 28-33

A total of 55 drugs and their human % absorption values have been made available by the authors. One compound, "0311C90", was obtained by authors from Glaxo-Wellcome and we have not provided its structure or values here in our files. Compounds "acebutolol HCl", "alprenolol HCl", "bupropion HCl", "labetatol HCl", "oxyprenolol HCl", "propranolol HCl", "ranitidine HCl", and "sotalol HCl" were retrieved as "acebutolol", "alprenolol", "bupropion", "labetatol", "oxyprenolol", "propranolol", "ranitidine" and "sotalol". To the best of our understanding, this should not matter for QSAR modeling purposes. Further, "terbutaline hemisulfate" was retrieved as "terbutaline".

QSAR World - Datasets - Irvine

S. Agatonovic-Kustrin, R. Beresford and A. Pauzi M. Yusof. Theoretically-derived molecular descriptors important in human intestinal absorption , J. Pharm. Biomed. Anal. 2001, 44(12), 1927 - 1937

86 drugs and their experimentally-derived Intestinal Absorption (%) values have been given. "Fluconasole" was retrieved as "Fluconazole" and "Hydrocortizone" as "hydrocortisone" from ChemIDplus. Drugs were either part of 'Training and testing data sets' or 'Validation data set'. This scheme has been indicated in a 'Label' column in the AMP file.

QSAR World - Datasets - Kustrin

Zhao YH, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G, Sherborne B, and Cooper I. Rate-limited Steps of Human Oral Absorption and QSAR Studies , Pharm Res., 2002, 19(10), 1446-57

QSAR World - Datasets - Zhao

HPLC of Betamethasone on Phenomenex Gemini 5u C18 with UV detection

Focused Libraries

Identifiers

Names and Synonyms
Database ID(s)

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(11b,16a)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

(11beta,16alpha)-9-Fluor-11,17,21-trihydroxy-16-methylpregna-1,4-dien-3,20-dion

(11beta,16alpha)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

(8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluor-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-on

(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(hydroxyacétyl)-10,13,16-triméthyl-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-3-one

(8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-17-glycoloyl-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

16.alpha.-Methyl-9.alpha.-fluoroprednisolone

16a-Methyl-9a-fluoro-1,4-pregnadiene-11b,17a,21-triol-3,20-dione

16a-Methyl-9a-fluoro-D1-hydrocortisone

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

31375_FLUKA

46165_RIEDEL

AI3-50934

C15643

CCRIS 7067

D00292

D1756_SIGMA

D4902_SIGMA

D6645_SIGMA

D8893_SIGMA

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Predicted Properties

Pred. Prop. (ACD/Labs)
Pred. Prop. (EPISuite)
NMRShiftDB
Exptl. Prop.

ACD/LogP:	1.87	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	1.87	ACD/LogD (pH 7.4):	1.87
ACD/BCF (pH 5.5):	15.49	ACD/BCF (pH 7.4):	15.49
ACD/KOC (pH 5.5):	247.46	ACD/KOC (pH 7.4):	247.45
#H bond acceptors:	5	#H bond donors:	3
#Freely Rotating Bonds:	5	Polar Surface Area:	61.83 Å²
Index of Refraction:	1.591	Molar Refractivity:	100.23 cm³
Molar Volume:	296.2 cm³	Polarizability:	39.73 10^-24cm³
Surface Tension:	56.5 dyne/cm	Density:	1.32 g/cm³
Flash Point:	297.5 °C	Enthalpy of Vaporization:	97.96 kJ/mol
Boiling Point:	568.2 °C at 760 mmHg	Vapour Pressure:	2.81E-15 mmHg at 25°C

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.72
    Log Kow (Exper. database match) =  1.83
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  1.94
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  508.92  (Adapted Stein & Brown method)
    Melting Pt (deg C):  216.77  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.81E-014  (Modified Grain method)
    MP  (exp database):  232 deg C
    Subcooled liquid VP: 9.82E-012 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):  75.14
       log Kow used: 1.94 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  89 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  66.5 mg/L (25 deg C)
        Exper. Ref:  EPA

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  58.572 mg/L
    Wat Sol (Exper. database match) =  89.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  66.50
       Exper. Ref:  EPA

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.15E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.993E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.94  (exp database)
  Log Kaw used:  -5.534  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.474
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1561
   Biowin2 (Non-Linear Model)     :   0.0003
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7584  (months      )
   Biowin4 (Primary Survey Model) :   2.8822  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5880
   Biowin6 (MITI Non-Linear Model):   0.0015
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7746
 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):  1.31E-009 Pa (9.82E-012 mm Hg)
  Log Koa (Koawin est  ): 7.474
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.29E+003 
       Octanol/air (Koa) model:  7.31E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.000585 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  69.5010 E-12 cm3/molecule-sec
      Half-Life =     0.154 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.847 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 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    :  95.97
      Log Koc:  1.982 

 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 = 0.794 (BCF = 6.22)
       log Kow used: 1.94 (expkow database)

 Volatilization from Water:
    Henry LC:  7.15E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.622E+004  hours   (676 days)
    Half-Life from Model Lake : 1.772E+005  hours   (7382 days)

 Removal In Wastewater Treatment:
    Total removal:               2.20  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.10  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       0.122           3.14         1000       
   Water     30.6            1.44e+003    1000       
   Soil      69.1            2.88e+003    1000       
   Sediment  0.113           1.3e+004     0          
     Persistence Time: 1.11e+003 hr

User Data

miscellaneous

Therapeutic Effect: Antiemetics,Glucocorticoids

No description available

Medical Subject Headings Classification

SimBioSys LASSO

Curation

RSC Databases