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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-02 21:57:33 UTC
Update Date2022-09-22 17:44:15 UTC
HMDB IDHMDB0240313
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Androsten-3beta,17beta-diol disulfate
Description4-Androsten-3beta,17beta-diol disulfate, also known as 4-androsten-3β,17β-diol disulfate, is classified as a member of the sulfated steroids. Sulfated steroids are sterol lipids containing a sulfate group attached to the steroid skeleton. 4-Androsten-3beta,17beta-diol disulfate is considered to be a practically insoluble (in water) and an extremely strong acidic compound. Human plasma levels of 4-androsten-3beta,17beta-diol disulfate were reported to be influenced by genetic variants in the gene SULT2A1 which codes for the enzyme dehydroepiandrosterone sulfotransferase (PMID: 24816252 ).
Structure
Data?1571939117
Synonyms
ValueSource
(3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulfate)ChEBI
(3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulfate)Generator
(3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulphate)Generator
(3b,17b)-Androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid)Generator
(3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulphate)Generator
(3beta,17beta)-Androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid)Generator
(3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulfate)Generator
(3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulphate)Generator
(3Β,17β)-androst-4-ene-3,17-diyl bis(hydrogen sulphuric acid)Generator
4-Androsten-3b,17b-diol disulfateGenerator
4-Androsten-3b,17b-diol disulfuric acidGenerator
4-Androsten-3b,17b-diol disulphateGenerator
4-Androsten-3b,17b-diol disulphuric acidGenerator
4-Androsten-3beta,17beta-diol disulfuric acidGenerator
4-Androsten-3beta,17beta-diol disulphateGenerator
4-Androsten-3beta,17beta-diol disulphuric acidGenerator
4-Androsten-3β,17β-diol disulfateGenerator
4-Androsten-3β,17β-diol disulfuric acidGenerator
4-Androsten-3β,17β-diol disulphateGenerator
4-Androsten-3β,17β-diol disulphuric acidGenerator
4-Androstenediol disulfuric acidHMDB
4-Androstenediol disulphateHMDB
4-Androstenediol disulphuric acidHMDB
4-Androstene-3b,17b-diol disulfateHMDB
4-Androstene-3b,17b-diol disulfuric acidHMDB
4-Androstene-3b,17b-diol disulphateHMDB
4-Androstene-3b,17b-diol disulphuric acidHMDB
4-Androstene-3beta,17beta-diol disulfuric acidHMDB
4-Androstene-3beta,17beta-diol disulphateHMDB
4-Androstene-3beta,17beta-diol disulphuric acidHMDB
4-Androstene-3β,17β-diol disulfateHMDB
4-Androstene-3β,17β-diol disulfuric acidHMDB
4-Androstene-3β,17β-diol disulphateHMDB
4-Androstene-3β,17β-diol disulphuric acidHMDB
4-Androstene-3beta,17beta-diol disulfateHMDB
Androst-4-en-3beta,17beta-ylene sulfateHMDB
Androst-4-en-3beta,17beta-ylene sulphateHMDB
Androst-4-en-3β,17β-ylene sulfateHMDB
Androst-4-en-3β,17β-ylene sulphateHMDB
Androst-4-ene-3beta,17beta-diol 3,17-disulfateHMDB
Androst-4-ene-3beta,17beta-diol 3,17-disulphateHMDB
Androst-4-ene-3β,17β-diol 3,17-disulfateHMDB
Androst-4-ene-3β,17β-diol 3,17-disulphateHMDB
Androstenediol disulfateHMDB
Androstenediol disulphateHMDB
4-Androsten-3beta,17beta-diol disulfateHMDB
Chemical FormulaC19H30O8S2
Average Molecular Weight450.56
Monoisotopic Molecular Weight450.138210274
IUPAC Name[(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxidanesulfonic acid
Traditional Name[(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]oxidanesulfonic acid
CAS Registry Number1357147-18-2
SMILES
[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C19H30O8S2/c1-18-9-7-13(26-28(20,21)22)11-12(18)3-4-14-15-5-6-17(27-29(23,24)25)19(15,2)10-8-16(14)18/h11,13-17H,3-10H2,1-2H3,(H,20,21,22)(H,23,24,25)/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyUWPTUYJASNIIJM-LOVVWNRFSA-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
  • Androstane-skeleton
  • Delta-4-steroid
  • 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-0.97ALOGPS
logP3.06ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.31 m³·mol⁻¹ChemAxon
Polarizability46.51 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]-231.930932474
DeepCCS[M+Na]+206.20230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Androsten-3beta,17beta-diol disulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O4533.2Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O3219.0Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@H](CC[C@]12C)OS(O)(=O)=O3678.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3573.1Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3508.2Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C4766.7Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3563.3Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3498.4Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O4749.1Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3577.4Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3707.3Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C4647.6Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3794.8Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3816.7Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C4879.8Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13800.2Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13822.3Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC14853.7Standard polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC14016.5Semi standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC14312.8Standard non polar33892256
4-Androsten-3beta,17beta-diol disulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC14757.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Androsten-3beta,17beta-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 - 4-Androsten-3beta,17beta-diol disulfate 10V, Positive-QTOFsplash10-0udi-0019800000-a7757eb786bf7e3ad8342019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Positive-QTOFsplash10-0zfr-0096000000-5c94c721117275f9900e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Positive-QTOFsplash10-00mp-1592000000-c76c3d31b5b1be5737312019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Negative-QTOFsplash10-0002-0005900000-64725de0ce689f591dd62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Negative-QTOFsplash10-0gi1-1079100000-902e7f94588ce21152e62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Negative-QTOFsplash10-0f8i-9065000000-a666caa78563c7dd062a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Positive-QTOFsplash10-0udi-0002900000-d64b550422eb6f346c742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Positive-QTOFsplash10-0zmi-0091000000-d9d6087fc9775370a1de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Positive-QTOFsplash10-0pb9-4961000000-592d2646aa22737a0ecb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 10V, Negative-QTOFsplash10-0002-0000900000-c8698967a7d5484751642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 20V, Negative-QTOFsplash10-0002-9000200000-1db080bae05d677ddd472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Androsten-3beta,17beta-diol disulfate 40V, Negative-QTOFsplash10-0002-9000100000-7d3e3cd58a127b09b14f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58163615
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87120982
PDB IDNot Available
ChEBI ID133124
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. Shin SY, Fauman EB, Petersen AK, Krumsiek J, Santos R, Huang J, Arnold M, Erte I, Forgetta V, Yang TP, Walter K, Menni C, Chen L, Vasquez L, Valdes AM, Hyde CL, Wang V, Ziemek D, Roberts P, Xi L, Grundberg E, Waldenberger M, Richards JB, Mohney RP, Milburn MV, John SL, Trimmer J, Theis FJ, Overington JP, Suhre K, Brosnan MJ, Gieger C, Kastenmuller G, Spector TD, Soranzo N: An atlas of genetic influences on human blood metabolites. Nat Genet. 2014 Jun;46(6):543-550. doi: 10.1038/ng.2982. Epub 2014 May 11. [PubMed:24816252 ]
  2. 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 ]