Metabolite 7-alpha-thiomethylspironolactone

Name

7-alpha-thiomethylspironolactone

Description

Not Available

Structure

Synonyms

(7R,8R,9S,10R,13S,14S,17R)-10,13-DIMETHYL-7-METHYLSULFANYL-SPIRO(2,6,7,8,9,11,12,14,15,16-DECAHYDRO-1H-CYCLOPENTA(A)PHENANTHRENE-17,5'-TETRAHYDROFURAN)-2',3-DIONE / 3-(3-OXO-7.ALPHA.-METHYLTHIO-17.BETA.-HYDROXY-4-ANDROSTEN-17.ALPHA.-YL)PROPIONIC ACID .GAMMA.-LACTONE / 7-DE(ACETYLTHIO)-7.ALPHA.-(METHYLTHIO)SPIRONOLACTONE / 7-THIOMETHYLSPIROLACTONE / 7.ALPHA.-(METHYLTHIO)SPIRONOLACTONE / 7.ALPHA.-(THIOMETHYL)SPIROLACTONE / 7.ALPHA.-(THIOMETHYL)SPIRONOLACTONE / SPIRONOLACTONE METABOLITE M4

External IDs

SC-26519

UNII

0YU66JY4WL

CAS number

38753-77-4

Weight

Average: 388.57
Monoisotopic: 388.207216064

Chemical Formula

C₂₃H₃₂O₃S

InChI Key

FWRDLPQBEOKIRE-RJKHXGPOSA-N

InChI

InChI=1S/C23H32O3S/c1-21-8-4-15(24)12-14(21)13-18(27-3)20-16(21)5-9-22(2)17(20)6-10-23(22)11-7-19(25)26-23/h12,16-18,20H,4-11,13H2,1-3H3/t16-,17-,18+,20+,21-,22-,23+/m0/s1

IUPAC Name

(1R,3aS,3bR,4R,9aR,9bS,11aS)-9a,11a-dimethyl-4-(methylsulfanyl)-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione

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

Reactions

Spironolactone

7-alpha-thiospironolactone
- 7-alpha-thiospironolactone
  
  Canrenone
- 7-alpha-thiospironolactone
  
  7-alpha-thiomethylspironolactone

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0009000000-46fd062b84bdb9b66c95
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000l-0009000000-1e6e5049789bc6b242a9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000f-0009000000-f5c614388426f60a6cb9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fkl-1329000000-6b9607613d8df2f3f8e6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-055r-0009000000-c65cf0fa39a1b2ddac89
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01r6-9868000000-6a500ad19079e611436e

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	194.63722	predicted	DeepCCS 1.0 (2019)
[M+H]+	196.53264	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.86162	predicted	DeepCCS 1.0 (2019)

External Links

ChemSpider: 142539
ChEMBL: CHEMBL3544705
ZINC: ZINC000006067531

Predicted Properties

Property	Value	Source
Water Solubility	0.00261 mg/mL	ALOGPS
logP	3.35	ALOGPS
logP	4.18	Chemaxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	17.94	Chemaxon
pKa (Strongest Basic)	-4.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	43.37 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	108.69 m³·mol^-1	Chemaxon
Polarizability	43.96 Å³	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite 7-alpha-thiomethylspironolactone

Structure for 7-alpha-thiomethylspironolactone

Collision Cross Sections (CCS)