You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2017-08-01 02:17:00 UTC
Update Date2019-10-04 16:21:54 UTC
HMDB IDHMDB0094682
Secondary Accession Numbers
  • HMDB94682
Metabolite Identification
Common Name5alpha-Androstan-3alpha,17beta-diol disulfate
Description5alpha-Androstan-3alpha,17beta-diol disulfate, also known as 5α-androstan-3α,17β-diol disulfuric acid, is classified as a member of the sulfated steroids. Sulfated steroids are sterol lipids containing a sulfate group attached to the steroid skeleton. 5alpha-Androstan-3alpha,17beta-diol disulfate is considered to be a practically insoluble (in water) and an extremely strong acidic compound. 5alpha-Androstan-3alpha,17beta-diol disulfate can be found in feces.
Structure
Data?1570206113
Synonyms
ValueSource
(3alpha,5alpha,17beta)-Androstane-3,17-diyl bis(hydrogen sulfate)ChEBI
(3a,5a,17b)-Androstane-3,17-diyl bis(hydrogen sulfate)Generator
(3a,5a,17b)-Androstane-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3a,5a,17b)-Androstane-3,17-diyl bis(hydrogen sulphate)Generator
(3a,5a,17b)-Androstane-3,17-diyl bis(hydrogen sulphuric acid)Generator
(3alpha,5alpha,17beta)-Androstane-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3alpha,5alpha,17beta)-Androstane-3,17-diyl bis(hydrogen sulphate)Generator
(3alpha,5alpha,17beta)-Androstane-3,17-diyl bis(hydrogen sulphuric acid)Generator
(3Α,5α,17β)-androstane-3,17-diyl bis(hydrogen sulfate)Generator
(3Α,5α,17β)-androstane-3,17-diyl bis(hydrogen sulfuric acid)Generator
(3Α,5α,17β)-androstane-3,17-diyl bis(hydrogen sulphate)Generator
(3Α,5α,17β)-androstane-3,17-diyl bis(hydrogen sulphuric acid)Generator
5a-Androstan-3a,17b-diol disulfateGenerator
5a-Androstan-3a,17b-diol disulfuric acidGenerator
5a-Androstan-3a,17b-diol disulphateGenerator
5a-Androstan-3a,17b-diol disulphuric acidGenerator
5alpha-Androstan-3alpha,17beta-diol disulfuric acidGenerator
5alpha-Androstan-3alpha,17beta-diol disulphateGenerator
5alpha-Androstan-3alpha,17beta-diol disulphuric acidGenerator
5Α-androstan-3α,17β-diol disulfateGenerator
5Α-androstan-3α,17β-diol disulfuric acidGenerator
5Α-androstan-3α,17β-diol disulphateGenerator
5Α-androstan-3α,17β-diol disulphuric acidGenerator
5a-Androstane-3a,17b-diol disulfateGenerator, HMDB
5a-Androstane-3a,17b-diol disulfuric acidGenerator, HMDB
5a-Androstane-3a,17b-diol disulphateGenerator, HMDB
5a-Androstane-3a,17b-diol disulphuric acidGenerator, HMDB
5alpha-Androstane-3alpha,17beta-diol disulfuric acidGenerator, HMDB
5alpha-Androstane-3alpha,17beta-diol disulphateGenerator, HMDB
5alpha-Androstane-3alpha,17beta-diol disulphuric acidGenerator, HMDB
5α-androstane-3α,17β-diol disulfateGenerator, HMDB
5α-androstane-3α,17β-diol disulfuric acidGenerator, HMDB
5α-androstane-3α,17β-diol disulphateGenerator, HMDB
5α-androstane-3α,17β-diol disulphuric acidGenerator, HMDB
5alpha-Androstan-3alpha,17beta-ylene sulfateHMDB
5alpha-Androstan-3alpha,17beta-ylene sulphateHMDB
5alpha-Androstane-3alpha,17beta-diol disulfateHMDB
5alpha-Androstane-3alpha,17beta-diol, 3,17-disulfateHMDB
5alpha-Androstane-3alpha,17beta-diol, 3,17-disulphateHMDB
5alpha-Androstane-3alpha,17beta-diol, bis(hydrogen sulfate)HMDB
5alpha-Androstane-3alpha,17beta-diol, bis(hydrogen sulphate)HMDB
5α-Androstan-3α,17β-ylene sulfateHMDB
5α-Androstan-3α,17β-ylene sulphateHMDB
5α-Androstane-3α,17β-diol disulfateHMDB
5α-Androstane-3α,17β-diol disulphateHMDB
5α-Androstane-3α,17β-diol, 3,17-disulfateHMDB
5α-Androstane-3α,17β-diol, 3,17-disulphateHMDB
5α-Androstane-3α,17β-diol, bis(hydrogen sulfate)HMDB
5α-Androstane-3α,17β-diol, bis(hydrogen sulphate)HMDB
Chemical FormulaC19H32O8S2
Average Molecular Weight452.58
Monoisotopic Molecular Weight452.153860338
IUPAC Name[(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxidanesulfonic acid
Traditional Name[(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxidanesulfonic acid
CAS Registry Number21152-49-8
SMILES
[H][C@@]12CC[C@H](OS(O)(=O)=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/C19H32O8S2/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/h12-17H,3-11H2,1-2H3,(H,20,21,22)(H,23,24,25)/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyJHFAETDERBWUOO-KHOSGYARSA-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
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.87ALOGPS
logP3.31ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area127.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.61 m³·mol⁻¹ChemAxon
Polarizability46.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-0149500000-9bb4f0ad0b2cf48f04a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0005900000-90e38cd71c7e9ac0a1f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1079100000-976c0cda8b6735ebbf41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-9065000000-ec746064aea15981d436Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0028900000-0c83ed2b26d09e0cc09fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0095000000-6b225ae37cae84f54042Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1492000000-56f2a979b080c814f6e9Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB066599
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound56639109
PDB IDNot Available
ChEBI ID133101
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.