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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:08 UTC
Update Date2017-10-23 19:04:01 UTC
HMDB IDHMDB0002759
Secondary Accession Numbers
  • HMDB02759
Metabolite Identification
Common NameAndrosterone sulfate
DescriptionAndrosterone sulfate (Andros-S) is the most abundant 5 alpha-reduced androgen metabolite in serum (PMID 8380602 ). Androsterone sulfate is clinically recognized as one of the major androgen metabolites found in urine. It is a cognate substrate for human dehydroepiandrosterone sulfotransferase, which catalyzes the transfer of the sulfonate group from 3'-phosphoadenosine-5'-phosphosulfate to dehydroepiandrosterone (DHEA) (PMID 14573603 ).
Structure
Thumb
Synonyms
ValueSource
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulfateChEBI
5alpha-Androstane-3alpha-ol-17-one sulfateChEBI
3a-Hydroxy-5a-androstan-17-one 3-sulfateGenerator
3a-Hydroxy-5a-androstan-17-one 3-sulfuric acidGenerator
3a-Hydroxy-5a-androstan-17-one 3-sulphateGenerator
3a-Hydroxy-5a-androstan-17-one 3-sulphuric acidGenerator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulfuric acidGenerator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphateGenerator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphuric acidGenerator
3α-hydroxy-5α-androstan-17-one 3-sulfateGenerator
3α-hydroxy-5α-androstan-17-one 3-sulfuric acidGenerator
3α-hydroxy-5α-androstan-17-one 3-sulphateGenerator
3α-hydroxy-5α-androstan-17-one 3-sulphuric acidGenerator
Androsterone sulfuric acidGenerator
Androsterone sulphateGenerator
Androsterone sulphuric acidGenerator
5a-Androstane-3a-ol-17-one sulfateGenerator
5a-Androstane-3a-ol-17-one sulfuric acidGenerator
5a-Androstane-3a-ol-17-one sulphateGenerator
5a-Androstane-3a-ol-17-one sulphuric acidGenerator
5alpha-Androstane-3alpha-ol-17-one sulfuric acidGenerator
5alpha-Androstane-3alpha-ol-17-one sulphateGenerator
5alpha-Androstane-3alpha-ol-17-one sulphuric acidGenerator
5α-androstane-3α-ol-17-one sulfateGenerator
5α-androstane-3α-ol-17-one sulfuric acidGenerator
5α-androstane-3α-ol-17-one sulphateGenerator
5α-androstane-3α-ol-17-one sulphuric acidGenerator
3alpha-Sulfate-5alpha-androstan-17-oneHMDB
5alpha-Androsterone sulfateHMDB
5alpha-Androsterone sulphateHMDB
Andros-SHMDB
Androsterone 3alpha-sulfateHMDB
Androsterone 3alpha-sulphateHMDB
Androsterone monosulfateHMDB
Androsterone monosulphateHMDB
Androsterone sulfate, (3alpha,5beta)-isomerMeSH
Androsterone sulfate, (3beta,5alpha)-isomerMeSH
Androsterone sulfate, (3beta,5beta)-isomerMeSH
Androsterone sulfate, sodium saltMeSH
Androsterone sulfate, sodium salt, (3alpha,5beta)-isomerMeSH
Androsterone sulfate, sodium salt, (3beta,5alpha)-isomerMeSH
Epiandrosterone sulfateMeSH
Chemical FormulaC19H30O5S
Average Molecular Weight370.504
Monoisotopic Molecular Weight370.18139476
IUPAC Name[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid
Traditional Namedheas
CAS Registry Number2479-86-9
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChI KeyZMITXKRGXGRMKS-HLUDHZFRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Androstane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

    Endocrine gland:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

  Molecular messenger:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP0.45ALOGPS
logP3.82ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.8 m³·mol⁻¹ChemAxon
Polarizability40.01 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0198000000-4c5a7a41e009f264e2deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0049000000-bebc98c547fc3453b68aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0091000000-bcf45b9068c011eeccc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lxt-4592000000-35783b6b3e3984a95594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-0159b1c3007356200d05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1092000000-8a8f3a15b4b976801efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ei-6090000000-e541f7c26cb75cbe027cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Epidermis
  • Gonads
  • Kidney
  • Liver
  • Muscle
  • Testes
Pathways
NameSMPDB/PathwhizKEGG
Androgen and Estrogen MetabolismPw000045Pw000045 greyscalePw000045 simpleMap00150
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.1 (0.80-21.4) uMAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.39 (0.0069-0.81) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023062
KNApSAcK IDNot Available
Chemspider ID140383
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrosterone sulfate
METLIN ID3559
PubChem Compound159663
PDB IDNot Available
ChEBI ID83037
References
Synthesis ReferencePelzer, Helmut; Staib, Wolfgang. Conjugated steroids. I. High-voltage paper electrophoresis of conjugated 17-keto steroids. Clinica Chimica Acta (1957), 2 407-15.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang HJ, Shi R, Rehse P, Lin SX: Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex. J Biol Chem. 2004 Jan 23;279(4):2689-96. Epub 2003 Oct 21. [PubMed:14573603 ]
  2. Zwicker H, Rittmaster RS: Androsterone sulfate: physiology and clinical significance in hirsute women. J Clin Endocrinol Metab. 1993 Jan;76(1):112-6. [PubMed:8380602 ]
  3. PLAGER JE: THE BINDING OF ANDROSTERONE SULFATE, ETHIOCHOLANOLONE SULFATE, AND DEHYDROISOANDROSTERONE SULFATE BY HUMAN PLASMA PROTEIN. J Clin Invest. 1965 Jul;44:1234-9. [PubMed:14328399 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
General function:
Involved in catalytic activity
Specific function:
Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:
STS
Uniprot ID:
P08842
Molecular weight:
65491.72