Metabolite 7-alpha-thiospironolactone

Name

7-alpha-thiospironolactone

Description

Not Available

Structure

Synonyms

(7R,8R,9S,10R,13S,14S,17R)-10,13-DIMETHYL-7-SULFANYL-SPIRO(2,6,7,8,9,11,12,14,15,16-DECAHYDRO-1H-CYCLOPENTA(A)PHENANTHRENE-17,5'-TETRAHYDROFURAN)-2',3-DIONE / 7.ALPHA.-THIOSPIROLACTONE / 7.ALPHA.-THIOSPIRONOLACTONE / DEACETYLSPIRONOLACTONE / MERCAPTOSPIRONOLACTONE / SPIRONOLACTONE METABOLITE M3

External IDs

SC-24813

UNII

4LH70U7H4Z

CAS number

38753-76-3

Weight

Average: 374.54
Monoisotopic: 374.191566

Chemical Formula

C₂₂H₃₀O₃S

InChI Key

NZCDWYJROUPYPT-NYTLBARGSA-N

InChI

InChI=1S/C22H30O3S/c1-20-7-3-14(23)11-13(20)12-17(26)19-15(20)4-8-21(2)16(19)5-9-22(21)10-6-18(24)25-22/h11,15-17,19,26H,3-10,12H2,1-2H3/t15-,16-,17+,19+,20-,21-,22+/m0/s1

IUPAC Name

(1R,3aS,3bR,4R,9aR,9bS,11aS)-9a,11a-dimethyl-4-sulfanyl-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])(S)CC2=CC(=O)CC[C@]12C

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	splash10-004i-0029000000-66a03e347eb19c345c9f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0009000000-0d2254cb88a9e8038ae0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-056s-0239000000-3e2046eed98f526520b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00bi-0019000000-95b58715f94f70994bd3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01r2-4975000000-394fcc3c0d00d641546d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05nb-0019000000-f2f524e68c3bbfc20351

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	189.12016	predicted	DeepCCS 1.0 (2019)
[M+H]+	191.01558	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.66794	predicted	DeepCCS 1.0 (2019)

External Links

ChemSpider: 106700
ChEBI: 185845
ChEMBL: CHEMBL3544689
ZINC: ZINC000005138852

Predicted Properties

Property	Value	Source
Water Solubility	0.00144 mg/mL	ALOGPS
logP	3.66	ALOGPS
logP	3.8	Chemaxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10	Chemaxon
pKa (Strongest Basic)	-4.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	43.37 Å²	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	104.04 m³·mol^-1	Chemaxon
Polarizability	41.75 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-thiospironolactone

Structure for 7-alpha-thiospironolactone

Collision Cross Sections (CCS)