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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2019-10-25 17:30:18 UTC
Update Date2022-03-07 03:18:19 UTC
HMDB IDHMDB0240579
Secondary Accession NumbersNone
Metabolite Identification
Common Name5alpha-Pregnan-3beta,20beta-diol 3-sulfate
Description5alpha-Pregnan-3beta,20beta-diol 3-sulfate, also known as 5α-pregnan-3β,20β-diol 3-sulfate or 5a-pregnan-3b,20b-diol 3-sulfuric acid, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Based on a literature review very few articles have been published on 5alpha-Pregnan-3beta,20beta-diol 3-sulfate.
Structure
Data?1572024879
Synonyms
ValueSource
5a-Pregnan-3b,20b-diol 3-sulfateGenerator
5a-Pregnan-3b,20b-diol 3-sulfuric acidGenerator
5a-Pregnan-3b,20b-diol 3-sulphateGenerator
5a-Pregnan-3b,20b-diol 3-sulphuric acidGenerator
5alpha-Pregnan-3beta,20beta-diol 3-sulfuric acidGenerator
5alpha-Pregnan-3beta,20beta-diol 3-sulphateGenerator
5alpha-Pregnan-3beta,20beta-diol 3-sulphuric acidGenerator
5Α-pregnan-3β,20β-diol 3-sulfateGenerator
5Α-pregnan-3β,20β-diol 3-sulfuric acidGenerator
5Α-pregnan-3β,20β-diol 3-sulphateGenerator
5Α-pregnan-3β,20β-diol 3-sulphuric acidGenerator
5alpha-Pregnan-3beta,20beta-diol monosulfateHMDB
5alpha-Pregnan-3beta,20beta-diol monosulphateHMDB
5alpha-Pregnan-3beta,20beta-diol sulfateHMDB
5alpha-Pregnan-3beta,20beta-diol sulphateHMDB
5Α-pregnan-3β,20β-diol 3-sulphic acidHMDB
5Α-pregnan-3β,20β-diol monosulfateHMDB
5Α-pregnan-3β,20β-diol monosulphateHMDB
5Α-pregnan-3β,20β-diol monosulphic acidHMDB
5Α-pregnan-3β,20β-diol sulfateHMDB
5Α-pregnan-3β,20β-diol sulphateHMDB
5Α-pregnan-3β,20β-diol sulphic acidHMDB
5alpha-Pregnan-3beta,20beta-diol 3-sulfateHMDB
Chemical FormulaC21H36O5S
Average Molecular Weight400.57
Monoisotopic Molecular Weight400.228345433
IUPAC Name[(1S,2S,5S,7S,10R,11S,14S,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2S,5S,7S,10R,11S,14S,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
CAS Registry Number64997-50-8
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@@H](C)O
InChI Identifier
InChI=1S/C21H36O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22H,4-12H2,1-3H3,(H,23,24,25)/t13-,14+,15+,16+,17-,18+,19+,20+,21-/m1/s1
InChI KeyZIVKBPVUJZDVBI-XFHAOOBSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • 20-hydroxysteroid
  • Pregnane-skeleton
  • Hydroxysteroid
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP0.89ALOGPS
logP2.49ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.93 m³·mol⁻¹ChemAxon
Polarizability45.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-234.15530932474
DeepCCS[M+Na]+208.17130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Pregnan-3beta,20beta-diol 3-sulfate[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@@H](C)O3534.9Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@@H](C)O3087.1Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@@H](C)O3357.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,1TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3244.9Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,1TMS,isomer #2C[C@@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3264.4Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3288.1Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3416.1Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3939.2Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,1TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3513.3Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,1TBDMS,isomer #2C[C@@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3482.6Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3744.1Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4011.7Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol 3-sulfate,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4095.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 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 - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 10V, Positive-QTOFsplash10-0f89-0019400000-1867b6cebeabf7bde3262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 20V, Positive-QTOFsplash10-0zg0-0395000000-323c052d8fcf386f14012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 40V, Positive-QTOFsplash10-0a4j-7950000000-c17af405e36599cab9182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 10V, Negative-QTOFsplash10-0002-0009000000-c31c0110c9d333eee7cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 20V, Negative-QTOFsplash10-0002-1009000000-75fe1e02e8f3dbb2d0f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol 3-sulfate 40V, Negative-QTOFsplash10-0002-4009000000-785b44709f54dd0e64c32021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
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 ID8085855
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9910204
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 References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]