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Spironolactone

ChemSpider ID: 5628
Molecular Formula: C₂₄H₃₂O₄S
Average mass: 416.573486 Da
Monoisotopic mass: 416.202118 Da
Systematic name

S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl] ethanethioate
SMILES and InChIs

SMILES:

O=C5O[C@@]4([C@@]3([C@H]([C@@H]2[C@H](SC(=O)C)C/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)CC4)C)CC5 Copied

Std. InChI:

InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1 Copied

Std. InChIKey:

LXMSZDCAJNLERA-ZHYRCANASA-N Copied
Cite this record
CSID:5628, http://www.chemspider.com/Chemical-Structure.5628.html (accessed 01:46, May 26, 2012) Copied

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

(7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone

17-Hydroxy-7a-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic Acid g-Lactone Acetate

3-(3-Oxo-7a-acetylthio-17b-hydroxy-4-androsten-17a-yl)propionic Acid g-Lactone

52-01-7 [RN]

Aldace

Aldopur

Almatol

Altex

Aquareduct

Deverol

More...

Diatensec

Duraspiron

éthanethioate de S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-diméthyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadécahydro-3'H-spiro[cyclopenta[a]phénanthrène-17,2'-furan]-7-yle]

ethanethioic acid, S-[(7R,8R,9S,10R,13S,14S,17R)-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-10,13-dimethyl-3,5'-dioxospiro[17H-cyclopenta[a]phenanthrene-17,2'(3'H)-furan]-7-yl] ester

Lacalmin

Lacdene

Laractone

Nefurofan

Osiren

Osyrol

S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthren-17,2'-furan]-7-yl]ethanthioat

S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl] ethanethioate [ACD/IUPAC Name]

Sagisal

Sincomen

Spiretic

Spiroderm

Spirolakton

Spirolone

Spironolactone [Wiki]

Spironolactone [BAN:INN:JAN] [INN] [JAN]

Spironolactone 17-Hydroxy-7-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylicAcid g-Lactone 7-Acetate

SPIRONOLACTONE A

Supra-puren

Suracton

Abbolactone

Aldactide

SNL

Spiroctanie

Sprioderm

Verospirone Opianin

(1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecan]-6'-ene-5,5'-dione

(7R,8R,9S,10R,13S,14S,17R)-7-acetylsulfanyl-10,13-dimethyl-spiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione

[52-01-7]

1/7/1952

17-HYDROXY-7α-MERCAPTO-3-OXO-17α-PREGN-4-ENE-21- CARBOXYLIC ACID, γ-LACTONE ACETATE

17-Hydroxy-7α-mercapto-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone acetate

17α-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7α-mercapto-3-oxo-, γ-lactone acetate

17-α-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7-α-mercapto-3-oxo-, γ-lactone acetate

17α-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7α-mercapto-3-oxo-, γ-lactone, acetate

200-133-6 [EINECS]

3-(3-Keto-7α-acetylthio-17β-hydroxy-4-androsten-17.alph a.-yl)propionic acid lactone

3-(3-Keto-7-α-acetylthio-17-β-hydroxy-4-androsten-17-α-yl)propionic acid lactone

3'-(3-Oxo-7-α-acetylthio-17-β-hydroxyandrost-4-en-17-β-yl)propionic acid lactone

4-18-00-01601 (Beilstein Handbook Reference) [Beilstein]

4-Pregnen-21-oic acid-17¦Á-ol-3-one-7¦Á-thiol ¦Ã-lactone 7-acetate; 7¦Á-(Acetylthio)-17¦Á-hydroxy-3-oxopregn-4-ene-21-carboxylic acid ¦Ã-lactone

4-Pregnen-21-oic acid-17α-ol-3-one-7α-thiol γ-lactone 7- acetate

4-Pregnen-21-oic acid-17α-ol-3-one-7α-thiol γ-lactone 7-acetate

57767 [Beilstein]

7-α- (acetylthio)-17-α-hydroxy-3-oxopregn-4-ene-21-carb oxylic acid, γ-lactone

7α-(acetylsulfanyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

7α-(Acetylthio)-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone

7-α-(acetylthio)-17-α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, γ-lactone (9CI)

7-α-Acetylthio-3-oxo-17-α-pregn-4-ene-21,17-β-carbolactone

Acelat

ALDACTAZIDE [Wiki]

Aldactazide (TN)

ALDACTONE [Wiki]

Aldactone A

Alderon

component of Aldactazide

Dira

espironolactona [Spanish] [INN]

espironolactona; spironolactone; spironolactonum

Euteberol

Melarcon

Pregn-4-ene-21-carboxylic acid, 7- (acetylthio)-17-hydroxy-3-oxo-, γ-lactone, (7α, 17α)-

Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, γ-lactone, (7α,17α)-

Spiresis

Spiridon [Wiki]

Spiro(17H-cyclopenta(a)phenauthrene-17,2'-(3'H)-furan)

Spiro[17H-cyclopenta[a]phenauthrene-17, 2'-(3'H)-furan]

Spiroctan

Spirolactone

Spirolang

Spirone

Spironocompren

spironolactonum [Latin]

spironolattone

Spironolattone [DCIT]

Spiro-Tablinen

Uractone

Urusonin

VEROSPIRON

Verospirone

Xenalon

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

BRN 0057767 [DBID]

C07310 [DBID]

D00443 [DBID]

HSDB 3184 [DBID]

NSC 150399 [DBID]

NSC150399 [DBID]

Prestwick0_000128 [DBID]

Prestwick1_000128 [DBID]

S3378_SIGMA [DBID]

SC 15983 [DBID]

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ChemSpider Searches

Properties

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Data supplied by datasources and users.

experimental physchem properties
- Solubility:
  
  Soluble to 100 mM in DMSO and to 50 mM in ethanol Tocris Bioscience
miscellaneous
- Therapeutic Effect:
  
  Aldosterone Antagonists,Diuretics

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	3.148	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	3.15	ACD/LogD (pH 7.4):	3.15
ACD/BCF (pH 5.5):	145.25	ACD/BCF (pH 7.4):	145.25
ACD/KOC (pH 5.5):	1228.17	ACD/KOC (pH 7.4):	1228.17
#H bond acceptors:	4	#H bond donors:	0
#Freely Rotating Bonds:	2	Polar Surface Area:	85.74 Å²
Index of Refraction:	1.586	Molar Refractivity:	112.688 cm³
Molar Volume:	335.8 cm³	Polarizability:	44.673 10^-24cm³
Surface Tension:	50.8870010375977 dyne/cm	Density:	1.241 g/cm³
Flash Point:	302.268 °C	Enthalpy of Vaporization:	88.93 kJ/mol
Boiling Point:	596.987 °C at 760 mmHg	Vapour Pressure:	0 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.88
    Log Kow (Exper. database match) =  2.78
       Exper. Ref:  Hansch,C et al. (1995)
    Log Kow (Exper. database match) =  2.26
       Exper. Ref:  Hansch,C & Leo,A (1985)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  530.08  (Adapted Stein & Brown method)
    Melting Pt (deg C):  226.65  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.75E-010  (Modified Grain method)
    MP  (exp database):  134.5 deg C
    Subcooled liquid VP: 4.72E-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):  28.38
       log Kow used: 2.26 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  22 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.5645 mg/L
    Wat Sol (Exper. database match) =  22.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.14E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.243E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.26  (exp database)
  Log Kaw used:  -8.332  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.592
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1784
   Biowin2 (Non-Linear Model)     :   0.0115
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7600  (months      )
   Biowin4 (Primary Survey Model) :   2.9931  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3719
   Biowin6 (MITI Non-Linear Model):   0.0347
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6212
 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):  6.29E-007 Pa (4.72E-009 mm Hg)
  Log Koa (Koawin est  ): 10.592
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.77 
       Octanol/air (Koa) model:  0.00959 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  0.434 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 113.4687 E-12 cm3/molecule-sec
      Half-Life =     0.094 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.131 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.996 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.389E+004
      Log Koc:  4.143 

 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 = 1.040 (BCF = 10.97)
       log Kow used: 2.26 (expkow database)

 Volatilization from Water:
    Henry LC:  1.14E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.048E+007  hours   (4.368E+005 days)
    Half-Life from Model Lake : 1.144E+008  hours   (4.765E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.57  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.47  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       0.0145          2.07         1000       
   Water     19.3            1.44e+003    1000       
   Soil      80.6            2.88e+003    1000       
   Sediment  0.109           1.3e+004     0          
     Persistence Time: 1.89e+003 hr

Click to predict properties on the Chemicalize site

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Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.33
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.10
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
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
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	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	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
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	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
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Kinases	TK, thymidine kinase	1kim	0.00

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Spironolactone

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Spironolactone

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