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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2019-10-25 20:29:00 UTC
Update Date2022-03-07 03:18:19 UTC
HMDB IDHMDB0240581
Secondary Accession NumbersNone
Metabolite Identification
Common Name5alpha-Pregnan-3beta,20beta-diol disulfate
Description5alpha-Pregnan-3beta,20beta-diol disulfate, also known as 5α-pregnan-3β,20β-diol disulfate or 5a-pregnan-3b,20b-diol disulfuric 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 disulfate.
Structure
Data?1572274744
Synonyms
ValueSource
5a-Pregnan-3b,20b-diol disulfateGenerator
5a-Pregnan-3b,20b-diol disulfuric acidGenerator
5a-Pregnan-3b,20b-diol disulphateGenerator
5a-Pregnan-3b,20b-diol disulphuric acidGenerator
5alpha-Pregnan-3beta,20beta-diol disulfuric acidGenerator
5alpha-Pregnan-3beta,20beta-diol disulphateGenerator
5alpha-Pregnan-3beta,20beta-diol disulphuric acidGenerator
5Α-pregnan-3β,20β-diol disulfateGenerator
5Α-pregnan-3β,20β-diol disulfuric acidGenerator
5Α-pregnan-3β,20β-diol disulphateGenerator
5Α-pregnan-3β,20β-diol disulphuric acidGenerator
5alpha-Pregnan-3beta,20beta-ylene sulfateHMDB
5alpha-Pregnan-3beta,20beta-ylene sulphateHMDB
5alpha-Pregnane-3beta,20beta-diol disulfateHMDB
5alpha-Pregnane-3beta,20beta-diol disulphateHMDB
5Α-pregnan-3β,20β-ylene sulfateHMDB
5Α-pregnan-3β,20β-ylene sulphateHMDB
5Α-pregnane-3β,20β-diol disulfateHMDB
5Α-pregnane-3β,20β-diol disulphateHMDB
5alpha-Pregnan-3beta,20beta-diol disulfateHMDB
Chemical FormulaC21H36O8S2
Average Molecular Weight480.63
Monoisotopic Molecular Weight480.185160467
IUPAC Name[(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyl-14-[(1R)-1-(sulfooxy)ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyl-14-[(1R)-1-(sulfooxy)ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
CAS Registry Number106300-16-7
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)OS(O)(=O)=O
InChI Identifier
InChI=1S/C21H36O8S2/c1-13(28-30(22,23)24)17-6-7-18-16-5-4-14-12-15(29-31(25,26)27)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19H,4-12H2,1-3H3,(H,22,23,24)(H,25,26,27)/t13-,14+,15+,16+,17-,18+,19+,20+,21-/m1/s1
InChI KeyLSQGWMYMIHQKSA-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
  • Pregnane-skeleton
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP-0.67ALOGPS
logP3.89ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.92 m³·mol⁻¹ChemAxon
Polarizability50.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-264.01430932474
DeepCCS[M+Na]+238.03230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Pregnan-3beta,20beta-diol disulfate[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)OS(O)(=O)=O4353.2Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate[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)OS(O)(=O)=O3442.8Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate[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)OS(O)(=O)=O3844.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C3661.0Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C3849.1Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4927.2Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C3695.6Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C3772.5Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C4941.9Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C3703.7Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C3969.8Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4805.2Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C3866.0Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4153.5Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C5025.8Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C3900.0Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C4100.0Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,1TBDMS,isomer #2C[C@@H](OS(=O)(=O)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@]12C5038.4Standard polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4118.3Semi standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4605.5Standard non polar33892256
5alpha-Pregnan-3beta,20beta-diol disulfate,2TBDMS,isomer #1C[C@@H](OS(=O)(=O)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@]12C4901.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 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 disulfate 10V, Negative-QTOFsplash10-004i-0000900000-1c0fbb6a069f510420ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 20V, Negative-QTOFsplash10-004i-3000900000-9c95bc2366d6b03ad6df2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 40V, Negative-QTOFsplash10-0002-9000100000-678a2530ff16e763f77d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 10V, Positive-QTOFsplash10-001i-0019300000-5a0685e4600eeef21bde2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 20V, Positive-QTOFsplash10-0019-0093000000-2d858cd8b20e2f26fad82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Pregnan-3beta,20beta-diol disulfate 40V, Positive-QTOFsplash10-053r-2391000000-a3409a8677245d01dc392021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 ID2339729
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3082277
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 ]