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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:31 UTC
Update Date2021-09-14 15:40:17 UTC
HMDB IDHMDB0061126
Secondary Accession Numbers
  • HMDB61126
Metabolite Identification
Common Name4,5-Dihydro-drospirenone-3-sulfate
Description4,5-Dihydro-drospirenone-3-sulfate is a metabolite of drospirenone. Drospirenone, also known as 1,2-dihydrospirorenone, is synthetic, steroidal progestin with additional antimineralocorticoid and weak antiandrogen properties which is used as a hormonal contraceptive. It is sold under the brand names Yasmin, Yasminelle, Yaz, Beyaz, Ocella, and Angeliq, all of which are combination products of drospirenone with an estrogen such as ethinylestradiol. (Wikipedia)
Structure
Data?1563866149
Synonyms
ValueSource
4,5-Dihydro-drospirenone-3-sulfuric acidGenerator
4,5-Dihydro-drospirenone-3-sulphateGenerator
4,5-Dihydro-drospirenone-3-sulphuric acidGenerator
Chemical FormulaC24H34O5S
Average Molecular Weight434.589
Monoisotopic Molecular Weight434.212694888
IUPAC Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
Traditional Name(2S,4R,10S,14S,16S,18S)-10,14-dimethyl-5'-oxospiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolane]-7-sulfonic acid
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O1
InChI Identifier
InChI=1S/C24H34O5S/c1-22-6-3-12(30(26,27)28)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(25)29-24/h12-18,20-21H,3-11H2,1-2H3,(H,26,27,28)/t12?,13-,14+,15-,16?,17?,18+,20?,21?,22-,23+,24?/m1/s1
InChI KeyZHIWICDXDMTIEM-AAQOLUSRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Tetrahydrofuran
  • Alkanesulfonic acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP1.12ALOGPS
logP3.07ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)-0.73ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity110.4 m³·mol⁻¹ChemAxon
Polarizability47.7 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.20631661259
DarkChem[M-H]-193.59731661259
DeepCCS[M-2H]-233.61530932474
DeepCCS[M+Na]+209.67230932474
AllCCS[M+H]+204.232859911
AllCCS[M+H-H2O]+202.232859911
AllCCS[M+NH4]+206.032859911
AllCCS[M+Na]+206.532859911
AllCCS[M-H]-202.832859911
AllCCS[M+Na-2H]-203.632859911
AllCCS[M+HCOO]-204.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,5-Dihydro-drospirenone-3-sulfateC[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O14156.4Standard polar33892256
4,5-Dihydro-drospirenone-3-sulfateC[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O13529.9Standard non polar33892256
4,5-Dihydro-drospirenone-3-sulfateC[C@]12CCC3C([C@H]4C[C@H]4C4CC(CC[C@]34C)S(O)(=O)=O)C1[C@@H]1C[C@@H]1C21CCC(=O)O13931.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,5-Dihydro-drospirenone-3-sulfate,1TMS,isomer #1C[C@]12CCC(S(=O)(=O)O[Si](C)(C)C)CC1[C@@H]1C[C@@H]1C1C2CC[C@@]2(C)C1[C@@H]1C[C@@H]1C21CCC(=O)O13663.6Semi standard non polar33892256
4,5-Dihydro-drospirenone-3-sulfate,1TMS,isomer #1C[C@]12CCC(S(=O)(=O)O[Si](C)(C)C)CC1[C@@H]1C[C@@H]1C1C2CC[C@@]2(C)C1[C@@H]1C[C@@H]1C21CCC(=O)O13678.7Standard non polar33892256
4,5-Dihydro-drospirenone-3-sulfate,1TMS,isomer #1C[C@]12CCC(S(=O)(=O)O[Si](C)(C)C)CC1[C@@H]1C[C@@H]1C1C2CC[C@@]2(C)C1[C@@H]1C[C@@H]1C21CCC(=O)O14224.2Standard polar33892256
4,5-Dihydro-drospirenone-3-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1CC[C@]2(C)C3CC[C@@]4(C)C(C3[C@H]3C[C@H]3C2C1)[C@@H]1C[C@@H]1C41CCC(=O)O13876.7Semi standard non polar33892256
4,5-Dihydro-drospirenone-3-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1CC[C@]2(C)C3CC[C@@]4(C)C(C3[C@H]3C[C@H]3C2C1)[C@@H]1C[C@@H]1C41CCC(=O)O14008.0Standard non polar33892256
4,5-Dihydro-drospirenone-3-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1CC[C@]2(C)C3CC[C@@]4(C)C(C3[C@H]3C[C@H]3C2C1)[C@@H]1C[C@@H]1C41CCC(=O)O14335.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cdj-0039200000-621e05258d19f492d39d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 10V, Positive-QTOFsplash10-000i-1007900000-6856048d0c9d173a1f912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 20V, Positive-QTOFsplash10-0h6r-0039100000-cbad5ebfff23c24d2d292017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 40V, Positive-QTOFsplash10-0006-2190000000-70973bb507f87249d9d12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 10V, Negative-QTOFsplash10-001i-1002900000-e95169f4809e9a97882d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 20V, Negative-QTOFsplash10-001i-2007900000-b41f8677923743b001082017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 40V, Negative-QTOFsplash10-001l-9001000000-f975c52679d9f108c58d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 10V, Negative-QTOFsplash10-001i-0000900000-bd768395a4b8c02c5c8f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 20V, Negative-QTOFsplash10-001i-0000900000-bd768395a4b8c02c5c8f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 40V, Negative-QTOFsplash10-001i-4002900000-d6a5f35285014dac3b692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 10V, Positive-QTOFsplash10-000i-0000900000-df5dcb19f91d486572c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 20V, Positive-QTOFsplash10-052k-0095700000-acde700425b11821dcb82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,5-Dihydro-drospirenone-3-sulfate 40V, Positive-QTOFsplash10-052b-2091200000-59aad6af2ce1ed362e112021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131770037
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available