Livestock Metabolome Database: Showing metabocard for Spironolactone (LMDB00646)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:33 UTC

Update Date

2016-07-20 21:02:23 UTC

Lmdb

LMDB00646

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Spironolactone

Description

A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Espironolactona	ChEBI
Spironolactonum	ChEBI
Spironolattone	ChEBI
Aldactone	Kegg
Aldactone a	HMDB
Aquareduct	HMDB
Espironolactona mundogen	HMDB
Frumikal	HMDB
Generosan brand OF spironolactone	HMDB
Merck dura brand OF spironolactone	HMDB
Mundogen brand OF spironolactone	HMDB
Spiro l.u.t.	HMDB
Spirobeta	HMDB
Spironone	HMDB
Wörwag brand OF spironolactone	HMDB
CT-Arzneimittel brand OF spironolactone	HMDB
Duraspiron	HMDB
Ashbourne brand OF spironolactone	HMDB
Azupharma brand OF spironolactone	HMDB
Flumach	HMDB
Pfizer brand OF spironolactone	HMDB
Practon	HMDB
Spirono-isis	HMDB
Betapharm brand OF spironolactone	HMDB
Spiro von CT	HMDB
Alphapharm brand OF spironolactone	HMDB
Alpharma brand OF spironolactone	HMDB
Alter brand OF spironolactone	HMDB
Hormosan brand OF spironolactone	HMDB
Jenaspiron	HMDB
Mayoly-spindler brand OF spironolactone	HMDB
Novo-spiroton	HMDB
Roche brand OF spironolactone	HMDB
Spiractin	HMDB
Spirogamma	HMDB
Spirolactone	HMDB
Spirono isis	HMDB
CT Arzneimittel brand OF spironolactone	HMDB
Cardel brand OF spironolactone	HMDB
Dexo brand OF spironolactone	HMDB
Espironolactona alter	HMDB
Jenapharm brand OF spironolactone	HMDB
Novo spiroton	HMDB
NovoSpiroton	HMDB
Novopharm brand OF spironolactone	HMDB
Pharmafrid brand OF spironolactone	HMDB
Searle brand OF spironolactone	HMDB
Spirolang	HMDB
Spirospare	HMDB
Veroshpiron	HMDB
Verospiron	HMDB
Verospirone	HMDB
Von CT, spiro	HMDB
CT, Spiro von	HMDB

Chemical Formula

C₂₄H₃₂O₄S

Average Molecular Weight

416.573

Monoisotopic Molecular Weight

416.202130202

IUPAC Name

(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

Traditional Name

spironolactone

CAS Registry Number

52-01-7

SMILES

[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@]([H])(CC2=CC(=O)CC[C@]12C)SC(C)=O

InChI Identifier

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

InChI Key

LXMSZDCAJNLERA-ZHYRCANASA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Spironolactones and derivatives

Alternative Parents

Substituents

Spironolactone
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Carbothioic s-ester
Cyclic ketone
Thiocarboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organosulfur compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

thioester (CHEBI:9241 )
3-oxo steroid (CHEBI:9241 )
methyl ketone (CHEBI:9241 )
oxaspiro compound (CHEBI:9241 )
steroid lactone (CHEBI:9241 )
Pregnane and derivatives [Fig] (C07310 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.1	ALOGPS
logP	3.64	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	18.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	113.5 m³·mol⁻¹	ChemAxon
Polarizability	46.03 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h2u-0109000000-b5dcae38bb499eaabba7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0000900000-5e2e1944e45fcef225d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0000900000-406c100eed5b6cdc3286	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0000900000-406c100eed5b6cdc3286	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0000900000-5e2e1944e45fcef225d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00or-0009200000-27849e6f24a460d7ac90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mn-0129000000-5819587c9e746750f5c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01tl-0192000000-6a35fab760c0aa732723	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-0009200000-defcf21ed513948675a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1009000000-ebe97ba9dd52376b449f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9004000000-2eccefa334bd23b4cdc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0002900000-f73d8e9df6c71e49d6eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uy1-0569200000-db11732abcc12259a54d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ukc-4593000000-33eba50454259079f605	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0001900000-329d630008c4558a5ec5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-7009500000-69af52e904d20a0c7b9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-8009000000-ba8deb5a673f3bd4868e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9836000000-9f600bd39c3b914c0b17	Spectrum