InChI=1/C21H28O2/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/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

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Search term: WWYNJERNGUHSAO-XUDSTZEEBP
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Inherent Properties, Identifiers and References

ChemSpider ID:	12560
Empirical Formula:	C₂₁H₂₈O₂
Molecular Weight:	312.4458
Nominal Mass:	312 Da
Average Mass:	312.4458 Da
Monoisotopic Mass:	312.20893 Da

Systematic Name:

(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

SMILES:

O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4

InChI:

InChI=1/C21H28O2/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/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

InChIKey:

WWYNJERNGUHSAO-XUDSTZEEBP

Std. InChI:

InChI=1S/C21H28O2/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/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

Std. InChIKey:

WWYNJERNGUHSAO-XUDSTZEESA-N

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Wikipedia Article(s)

Levonorgestrel (or l-norgestrel or D-norgestrel) is a synthetic progestogen used as an active ingredient in some hormonal contraceptives. Read more... or Edit at Wikipedia...

Norplant is a form of birth control developed by the Population Council that was first approved in 1983 in Finland, where it was manufactured by Leiras Oy Pharmaceuticals. The original Norplant consisted of a set of six small (2.4 mm × 34 mm) silicone capsules, each filled with 36 mg of levonorgestrel (a progestin used in many birth control pills) implanted subdermally in the upper arm and effective for five years.Norplant The original (six capsule) Norplant's production has been phased out; USAID's contract ran until December 2006.CCP: Pearl of the Week The original (six capsule) Norplant was approved by the U.S. Food and Drug Administration (FDA) in 1990 and marketed in the United States in 1991 by Wyeth Pharmaceuticals having been developed by Sheldon Segal. Norplant distribution in the United States ended in 2002; limited supplies still remained in the U.S. until 2004. Norplant was withdrawn from the UK market in 1999.BBC News | Health | Contraceptive implant withdrawn Norplant II (Norplant-2, Jadelle), also developed by the Population Council and manufactured by Schering Oy, consists of two small (2.5 mm × 43 mm) silicone rods each containing 75 mg of levonorgestrel in a polymer matrix, instead of six capsules. It was approved May 31, 1996 by the FDA as being effective for three years; it was subsequently approved November 22, 2002 by the FDA as being effective for five years. Jadelle has not been marketed in the United States;Population Council | Jadelle Implants FAQ General Info Jadelle is the successor to the original Norplant in USAID's contract beginning January 2007.Pearl of the Week Read more... or Edit at Wikipedia...

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Supplemental Information

Links & References

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

Names and Synonyms

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

(17a)-(-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one

(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one

(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

(8R,9S,10R,13S,14S,17R)-13-éthyl-17-éthynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-3H-cyclopenta[a]phénanthrén-3-one

(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (non-preferred name)

(8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on

13-BETA-ETHYL-17-ALPHA-ETHYNYL-17-BETA-HYDROXYGON-4-EN-3-ONE

13b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one

13-Ethyl-17a-ethynyl-17-hydroxygon-4-en-3-one

13-Ethyl-17-ethynyl-17b-hydroxy-4-gonen-3-one

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Database ID(s)

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

ACD/Labs Predicted Properties

ACD/LogP:	3.92	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	3.92	ACD/LogD (pH 7.4):	3.92
ACD/BCF (pH 5.5):	557.22	ACD/BCF (pH 7.4):	557.22
ACD/KOC (pH 5.5):	3215.19	ACD/KOC (pH 7.4):	3215.18
#H bond acceptors:	2	#H bond donors:	1
#Freely Rotating Bonds:	2	Polar Surface Area:	26.3 Å²
Index of Refraction:	1.571	Molar Refractivity:	90.18 cm³
Molar Volume:	274.3 cm³	Polarizability:	35.75 10^-24cm³
Surface Tension:	48.3 dyne/cm	Density:	1.13 g/cm³
Flash Point:	195.4 °C	Enthalpy of Vaporization:	82.99 kJ/mol
Boiling Point:	459.1 °C at 760 mmHg	Vapour Pressure:	2.32E-10 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.48

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  411.88  (Adapted Stein & Brown method)
    Melting Pt (deg C):  168.68  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1E-009  (Modified Grain method)
    MP  (exp database):  206 deg C
    Subcooled liquid VP: 8.28E-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):  35.84
       log Kow used: 3.48 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  8.991 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.70E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.147E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.48  (KowWin est)
  Log Kaw used:  -7.502  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.982
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2378
   Biowin2 (Non-Linear Model)     :   0.0048
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0620  (months      )
   Biowin4 (Primary Survey Model) :   3.0678  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2992
   Biowin6 (MITI Non-Linear Model):   0.0469
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.1537
 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):  1.1E-005 Pa (8.28E-008 mm Hg)
  Log Koa (Koawin est  ): 10.982
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.272 
       Octanol/air (Koa) model:  0.0236 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.908 
       Mackay model           :  0.956 
       Octanol/air (Koa) model:  0.653 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.5600 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.130 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.396749 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.718 Hrs
   Fraction sorbed to airborne particulates (phi): 0.932 (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 = 1.979 (BCF = 95.38)
       log Kow used: 3.48 (estimated)

 Volatilization from Water:
    Henry LC:  7.7E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.344E+006  hours   (5.6E+004 days)
    Half-Life from Model Lake : 1.466E+007  hours   (6.109E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              12.58  percent
    Total biodegradation:        0.18  percent
    Total sludge adsorption:    12.40  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       0.0293          1.41         1000       
   Water     13              1.44e+003    1000       
   Soil      85.9            2.88e+003    1000       
   Sediment  1.06            1.3e+004     0          
     Persistence Time: 1.83e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 2, 0, 0, 1, 2, 25, 0, 0, 4, 0, 0, 1, 1, 2, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.42
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.41
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.28
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.10
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.01
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00

Feedback

Date	Severity	Status	Feedback
11/02/2009 22:01:34	Low	Fixed	2 structures for levonorgestrel Verdict: Fixed