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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2017-03-23 03:53:14 UTC
Update Date2022-09-22 17:44:12 UTC
HMDB IDHMDB0062544
Secondary Accession Numbers
  • HMDB0000386
  • HMDB00386
  • HMDB0062611
  • HMDB62544
  • HMDB62611
Metabolite Identification
Common Name16alpha-Hydroxy DHEA 3-sulfate
Description16alpha-Hydroxy DHEA 3-sulfate (16α-OH-DHEAS), also known as 3beta,16alpha-Dihydroxyandrostenone sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. 16alpha-Hydroxy DHEA 3-sulfate originates mainly from the fetus and is a precursor for placental estriol biosynthesis (PMID: 24717977 ). 16alpha-Hydroxy DHEA 3-sulfate is a normal human metabolite identified in the placenta and breast milk of pregnant women. The size of the neonate's adrenal glands is in direct relation to the levels of 16alpha-Hydroxy DHEA 3-sulfate in pregnancy (PMID: 2963083 , 2974194 , 6216072 , 6220027 , 6220952 , 6445373 ).
Structure
Data?1600361582
Synonyms
ValueSource
16a-Hydroxydehydroepiandrosterone 3-sulfateGenerator
16a-Hydroxydehydroepiandrosterone 3-sulfuric acidGenerator
16a-Hydroxydehydroepiandrosterone 3-sulphateGenerator
16a-Hydroxydehydroepiandrosterone 3-sulphuric acidGenerator
16alpha-Hydroxydehydroepiandrosterone 3-sulfuric acidGenerator
16alpha-Hydroxydehydroepiandrosterone 3-sulphateGenerator
16alpha-Hydroxydehydroepiandrosterone 3-sulphuric acidGenerator
16α-Hydroxydehydroepiandrosterone 3-sulfateGenerator
16α-hydroxydehydroepiandrosterone 3-sulfuric acidGenerator
16α-Hydroxydehydroepiandrosterone 3-sulphateGenerator
16α-hydroxydehydroepiandrosterone 3-sulphuric acidGenerator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, ChEBI
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, ChEBI
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
(3β)-16α-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, Generator
(3β)-16α-hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3β)-16α-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3β)-16α-hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
(3β,16α)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfateHMDB, Generator
(3β,16α)-16-hydroxy-17-oxoandrost-5-en-3-yl sulfuric acidHMDB, Generator
(3β,16α)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphateHMDB, Generator
(3β,16α)-16-hydroxy-17-oxoandrost-5-en-3-yl sulphuric acidHMDB, Generator
16a-Hydroxy-DHEA 3-sulfateHMDB, Generator
16a-Hydroxy-DHEA 3-sulfuric acidHMDB, Generator
16a-Hydroxy-DHEA 3-sulphateHMDB, Generator
16a-Hydroxy-DHEA 3-sulphuric acidHMDB, Generator
16alpha-Hydroxy-DHEA 3-sulfateHMDB, ChEBI
16alpha-Hydroxy-DHEA 3-sulfuric acidHMDB, Generator
16alpha-Hydroxy-DHEA 3-sulphateHMDB, Generator
16alpha-Hydroxy-DHEA 3-sulphuric acidHMDB, Generator
16α-Hydroxy-DHEA 3-sulfateHMDB, Generator
16α-hydroxy-DHEA 3-sulfuric acidHMDB, Generator
16α-Hydroxy-DHEA 3-sulphateHMDB, Generator
16α-hydroxy-DHEA 3-sulphuric acidHMDB, Generator
3b-Sulfooxy-16a-hydroxyandrost-5-en-17-oneHMDB, Generator
3b-Sulphooxy-16a-hydroxyandrost-5-en-17-oneHMDB, Generator
3beta-Sulfooxy-16alpha-hydroxyandrost-5-en-17-oneHMDB, ChEBI
3beta-Sulphooxy-16alpha-hydroxyandrost-5-en-17-oneHMDB, Generator
3β-Sulfooxy-16α-hydroxyandrost-5-en-17-oneHMDB, Generator
3β-sulphooxy-16α-hydroxyandrost-5-en-17-oneHMDB, Generator
(3beta,16alpha)-16-Hydroxy-3-(sulfooxy)androst-5-en-17-oneHMDB
(3β,16α)-16-Hydroxy-3-(sulfooxy)androst-5-en-17-oneHMDB
16alpha-Hydroxy DHEA 3-sulfateHMDB
16alpha-Hydroxy DHEA 3-sulphateHMDB
16alpha-Hydroxy DHEA sulfateHMDB
16alpha-Hydroxy DHEA sulphateHMDB
16alpha-Hydroxy-DHEA sulfateHMDB
16alpha-Hydroxy-DHEA sulphateHMDB
16alpha-Hydroxydehydroepiandrosterone 3-sulfateHMDB
16alpha-Hydroxydehydroisoandrosterone sulfateHMDB
16alpha-Hydroxydehydroisoandrosterone sulphateHMDB
16alpha-OH DHEASHMDB
16alpha-OH-DHEA-3SHMDB
16alpha-OH-DHEA-SHMDB
16alpha-OH-DHEASHMDB
16α-Hydroxy DHEA 3-sulfateHMDB
16α-Hydroxy DHEA 3-sulphateHMDB
16α-Hydroxy DHEA sulfateHMDB
16α-Hydroxy DHEA sulphateHMDB
16α-Hydroxy-DHEA sulfateHMDB
16α-Hydroxy-DHEA sulphateHMDB
16α-Hydroxydehydroisoandrosterone sulfateHMDB
16α-Hydroxydehydroisoandrosterone sulphateHMDB
16α-OH DHEASHMDB
16α-OH-DHEA-3SHMDB
16α-OH-DHEA-SHMDB
16α-OH-DHEASHMDB
3beta,16alpha-Dihydroxy-5-androsten-17-one 3-sulfateHMDB
3beta,16alpha-Dihydroxy-5-androsten-17-one 3-sulphateHMDB
3β,16α-Dihydroxy-5-androsten-17-one 3-sulfateHMDB
3β,16α-Dihydroxy-5-androsten-17-one 3-sulphateHMDB
(3beta,16alpha)-3,16-Dihydroxyandrost-5-en-17-one sulfateHMDB
(3beta,16alpha)-3,16-Dihydroxyandrost-5-en-17-one sulphateHMDB
(3β,16α)-3,16-Dihydroxyandrost-5-en-17-one sulfateHMDB
(3β,16α)-3,16-Dihydroxyandrost-5-en-17-one sulphateHMDB
3b,16a-Dihydroxyandrostenone sulfateHMDB
3b,16a-Dihydroxyandrostenone sulphateHMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-one sulfateHMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-one sulphateHMDB
3beta,16alpha-Dihydroxyandrostenone sulfateHMDB
3beta,16alpha-Dihydroxyandrostenone sulphateHMDB
3β,16α-Dihydroxyandrost-5-en-17-one sulfateHMDB
3β,16α-Dihydroxyandrost-5-en-17-one sulphateHMDB
3β,16α-Dihydroxyandrostenone sulfateHMDB
3β,16α-Dihydroxyandrostenone sulphateHMDB
Chemical FormulaC19H28O6S
Average Molecular Weight384.49
Monoisotopic Molecular Weight384.160659796
IUPAC Name[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
CAS Registry Number4873-65-8
SMILES
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C19H28O6S/c1-18-7-5-12(25-26(22,23)24)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)21/h3,12-16,20H,4-10H2,1-2H3,(H,22,23,24)/t12-,13+,14-,15-,16+,18-,19-/m0/s1
InChI KeyALBNSVAJDFJRKQ-DNKQKWOHSA-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
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 16-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • Delta-5-steroid
  • Sulfate-ester
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.078 g/lALOGPS
LogP1.22ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.12ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.14 m³·mol⁻¹ChemAxon
Polarizability40.69 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]-220.83230932474
DeepCCS[M+Na]+195.26730932474
AllCCS[M+H]+191.532859911
AllCCS[M+H-H2O]+189.132859911
AllCCS[M+NH4]+193.732859911
AllCCS[M+Na]+194.332859911
AllCCS[M-H]-189.332859911
AllCCS[M+Na-2H]-189.832859911
AllCCS[M+HCOO]-190.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16alpha-Hydroxy DHEA 3-sulfate[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O3663.6Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O2809.5Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O3249.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16alpha-Hydroxy DHEA 3-sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O3236.3Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O)C2=O3246.4Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C3216.3Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O3287.2Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O3303.0Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O3997.1Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3245.3Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3202.9Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C4059.5Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C3232.9Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C3207.2Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C3959.1Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3265.8Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3399.2Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3901.5Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3498.5Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@@H](O)C(=O)[C@@]4(C)CC[C@@H]32)C13485.3Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3472.3Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3745.4Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3908.6Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O4151.0Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]2C13742.1Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]2C13774.5Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]2C14211.8Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3679.8Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3787.2Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4128.1Standard polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13907.0Semi standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C14227.8Standard non polar33892256
16alpha-Hydroxy DHEA 3-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C14083.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0cdl-0049000000-273a75dc3d6141b9788c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate GC-MS (1 TMS) - 70eV, Positivesplash10-0096-1049800000-47818e0e6c4513508f922017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16alpha-Hydroxy DHEA 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 - 16alpha-Hydroxy DHEA 3-sulfate 10V, Positive-QTOFsplash10-000i-0049000000-ae4f8e4741067f9517ce2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 20V, Positive-QTOFsplash10-000i-0091000000-5484c08bc6ae083370062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 40V, Positive-QTOFsplash10-0cdj-2690000000-0b46374982741b156bdc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 10V, Negative-QTOFsplash10-001i-0019000000-23a63b39a7b42e2be3502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 20V, Negative-QTOFsplash10-0udr-0059000000-03cbbc461804a913280a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 40V, Negative-QTOFsplash10-0f80-6093000000-9277a26e795d1d7493dd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 10V, Positive-QTOFsplash10-000i-0019000000-8ae59fa662a1ec3024692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 20V, Positive-QTOFsplash10-000i-0292000000-e74355bcadf5363f37a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 40V, Positive-QTOFsplash10-052f-3941000000-8caacde77c9e4e47392a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 10V, Negative-QTOFsplash10-001i-0009000000-5c281ab6096b4ad829242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 20V, Negative-QTOFsplash10-001i-1009000000-7f5e5a2d241c356bfa102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16alpha-Hydroxy DHEA 3-sulfate 40V, Negative-QTOFsplash10-002b-5009000000-1642eed98c9ed3da713b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.432 +/- 0.0468 uMAdult (>18 years old)Female
Pregnancy (not in labour)
details
BloodDetected and Quantified0.349 +/- 0.0416 uMAdult (>18 years old)FemalePregnancy (onset of labour) details
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 IDFDB034847
KNApSAcK IDNot Available
Chemspider ID24850136
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20848951
PDB IDNot Available
ChEBI ID87774
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceEasterling, William E., Jr.; Simmer, Hans H.; Dignam, William J.; Frankland, Marjorie V.; Naftolin, Frederick. Neutral C19 steroids and steroid sulfates in human pregnancy. II. Dehydroepiandrosterone sulfate, 16a-hydroxydehydroepiandrosterone, and 16a-hydroxydehydroepiandrosterone sulfate in maternal and fetal blood of pregnancies with anencephalic and normal fetuses. Steroids (1966), 8(2), 157-78.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Schweigmann H, Sanchez-Guijo A, Ugele B, Hartmann K, Hartmann MF, Bergmann M, Pfarrer C, Doring B, Wudy SA, Petzinger E, Geyer J, Grosser G: Transport of the placental estriol precursor 16alpha-hydroxy-dehydroepiandrosterone sulfate (16alpha-OH-DHEAS) by stably transfected OAT4-, SOAT-, and NTCP-HEK293 cells. J Steroid Biochem Mol Biol. 2014 Sep;143:259-65. doi: 10.1016/j.jsbmb.2014.03.013. Epub 2014 Apr 6. [PubMed:24717977 ]
  7. 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 ]
  8. Branchaud CL, Goodyer CG, Lipowski LS: Progesterone and estrogen production by placental monolayer cultures: effect of dehydroepiandrosterone and luteinizing hormone-releasing hormone. J Clin Endocrinol Metab. 1983 Apr;56(4):761-6. doi: 10.1210/jcem-56-4-761. [PubMed:6220027 ]
  9. Matsumura I, Hashino M, Maruyama S, Yanaihara T, Nakayama T: [Relation between size of fetal and neonatal adrenal glands and steroid levels in maternal and neonatal serum]. Nihon Sanka Fujinka Gakkai Zasshi. 1987 Dec;39(12):2125-32. [PubMed:2963083 ]
  10. Raju U, Levitz M, Jacobowitz G, Fleisher M, Bencsath FA, Field FH, Breed CN, Naganuma H, Bradlow HL: Quantification of the sulfates of 16 alpha-hydroxy androgens that are possible precursors of estriol-3-sulfate in human breast cyst fluid. Steroids. 1987 Oct-Dec;50(4-6):559-74. doi: 10.1016/0039-128x(87)90039-0. [PubMed:2974194 ]
  11. Nakayama T, Yanaihara T: Placental sulfatase deficiency. Biochemical and clinical aspects. Contrib Gynecol Obstet. 1982;9:145-56. [PubMed:6216072 ]
  12. Dibbelt L, Kuss E: Human placental steroid-sulfatase. Kinetics of the in-vitro hydrolysis of dehydroepiandrosterone 3-sulfate and of 16 alpha-hydroxydehydroepiandrosterone 3-sulfate. Hoppe Seylers Z Physiol Chem. 1983 Feb;364(2):187-91. [PubMed:6220952 ]
  13. Yamaji T, Ishibashi M, Katayama S, Kosaka K: Serum 16 beta-hydroxydehydroepiandrosterone sulfate in man. J Clin Endocrinol Metab. 1980 May;50(5):955-60. doi: 10.1210/jcem-50-5-955. [PubMed:6445373 ]
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.