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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:08 UTC
Update Date2021-09-14 15:41:24 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 ). Androsterone sulfate has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752255
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
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
Androsterone sulfuric acidGenerator
Androsterone sulphateGenerator
Androsterone 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)-isomerHMDB
Androsterone sulfate, (3beta,5alpha)-isomerHMDB
Androsterone sulfate, (3beta,5beta)-isomerHMDB
Androsterone sulfate, sodium saltHMDB
Androsterone sulfate, sodium salt, (3alpha,5beta)-isomerHMDB
Androsterone sulfate, sodium salt, (3beta,5alpha)-isomerHMDB
Epiandrosterone sulfateHMDB
Androsterone 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
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
  • 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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.01731661259
DarkChem[M-H]-177.58231661259
DeepCCS[M-2H]-225.08330932474
DeepCCS[M+Na]+199.46330932474
AllCCS[M+H]+189.832859911
AllCCS[M+H-H2O]+187.432859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.732859911
AllCCS[M-H]-187.632859911
AllCCS[M+Na-2H]-188.132859911
AllCCS[M+HCOO]-188.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Androsterone sulfate[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)=O3214.2Standard polar33892256
Androsterone sulfate[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)=O2906.0Standard non polar33892256
Androsterone sulfate[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)=O3154.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Androsterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3104.8Semi standard non polar33892256
Androsterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3016.3Standard non polar33892256
Androsterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3797.1Standard polar33892256
Androsterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3074.9Semi standard non polar33892256
Androsterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2848.6Standard non polar33892256
Androsterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3829.1Standard polar33892256
Androsterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3103.7Semi standard non polar33892256
Androsterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3070.7Standard non polar33892256
Androsterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3742.0Standard polar33892256
Androsterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13329.3Semi standard non polar33892256
Androsterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13337.2Standard non polar33892256
Androsterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13919.5Standard polar33892256
Androsterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3332.0Semi standard non polar33892256
Androsterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3116.1Standard non polar33892256
Androsterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3979.4Standard polar33892256
Androsterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[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@]12C3577.9Semi standard non polar33892256
Androsterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[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@]12C3609.4Standard non polar33892256
Androsterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[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@]12C3910.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0198000000-4c5a7a41e009f264e2de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone 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 - Androsterone sulfate 10V, Positive-QTOFsplash10-00di-0049000000-bebc98c547fc3453b68a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 20V, Positive-QTOFsplash10-00di-0091000000-bcf45b9068c011eeccc92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 40V, Positive-QTOFsplash10-0lxt-4592000000-35783b6b3e3984a955942016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 10V, Negative-QTOFsplash10-014i-0029000000-0159b1c3007356200d052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 20V, Negative-QTOFsplash10-000i-1092000000-8a8f3a15b4b976801efb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 40V, Negative-QTOFsplash10-00ei-6090000000-e541f7c26cb75cbe027c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 20V, Negative-QTOFsplash10-014i-1009000000-4b958c48d4c246f8639b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 40V, Negative-QTOFsplash10-0002-9005000000-ccff0fd3b8b51e4232062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 10V, Positive-QTOFsplash10-00di-0019000000-ed6f6b38f66a512fd98c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 20V, Positive-QTOFsplash10-0fk9-0292000000-16d0ae2e88a442fd375b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone sulfate 40V, Positive-QTOFsplash10-052b-3920000000-49e4315f36f0eafbe6ca2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Epidermis
  • Kidney
  • Liver
  • Ovary
  • Placenta
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.1 (0.80-21.4) uMAdult (>18 years old)MaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.39 (0.0069-0.81) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  4. 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 ]

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