Adrenosterone (CHEM036235)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:20:05 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036235
Identification
Common NameAdrenosterone
ClassSmall Molecule
DescriptionAdrenosterone, also known as Adrenosterone or NSC 12166, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Adrenosterone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Adrenosterone can be biosynthesized from 11b-hydroxyandrost-4-ene-3,17-dione through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In cattle, adrenosterone is involved in the metabolic pathway called the androstenedione metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Keto-androstenedioneChEBI
11-KetoandrostenedioneChEBI
11-oxoChEBI
11-Oxoandrost-4-ene-3,17-dioneChEBI
11-OxoandrostenedioneChEBI
11-Oxy-4-androstenedioneChEBI
4-Androsten-3,11,17-trioneChEBI
AndrenosteroneChEBI
Androst-4-ene-3,11,17-trioneChEBI
NSC 12166ChEBI
Reichstein's substance gChEBI
4-Androstene-3,11,17-trioneHMDB
Adrenosterone, 3H-labeledHMDB
Chemical FormulaC19H24O3
Average Molecular Mass300.392 g/mol
Monoisotopic Mass300.173 g/mol
CAS Registry Number382-45-6
IUPAC Name(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione
Traditional Nameadrenosterone
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1
InChI KeyRZRPTBIGEANTGU-IRIMSJTPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 17-oxosteroid
  • 11-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP2.42ALOGPS
logP3.01ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)17.99ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.21 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.27 m³·mol⁻¹ChemAxon
Polarizability33.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-dda2aae9c4577545506cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-dda2aae9c4577545506cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1590000000-60fcf2c287c8dac542eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ab9-2940000000-06e07dc51a896789d933Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0290000000-a6dda3c4c0b1e8e4c477Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-572505448243920d7c46Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-6a4af6e2a1477f91dfbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-57c8256a5ea31b9519f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1091000000-6b6dae7a99821b529938Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1092000000-9361c41ea86f032c634bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-6d600d8c52e480412d37Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-af6aba5ffbd5525ba43aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ab9-2940000000-06e07dc51a896789d933Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0596-3910000000-521e74db879ee9f81a3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0973000000-767c7b546b71c185a624Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0469000000-25e6987364697bc536e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-059fceb486c74e543289Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0069000000-51d9ddcfd1d7b8a3e20cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l7i-0291000000-7b42bb8a716d4c0700e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9j-2490000000-c88e67e966734b1d65eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-34ecec5ab91ebc5e78ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-4c027780977d32f6a16eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-2090000000-cdcd813d0ed227d587c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dd82c6133109d0e6e28eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-ff5973ba5b3491dd86a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-4190000000-b9abb2323ddbbd68f5caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-2789ee380fa1a8c91727Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0191000000-4cdffaa52886ce780121Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006772
FooDB IDFDB024074
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-18926
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAdrenosterone
Chemspider ID194597
ChEBI ID2495
PubChem Compound ID223997
Kegg Compound IDC05285
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10469997
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12434991
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12460593
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=13061495
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=13414169
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14288792
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14297229
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=14308712
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16216911
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17360211
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17889091
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20355175
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2295425
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22987608
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23685396
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25435279
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25917864
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26478560
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26865584
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=27154751
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=27889993
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=27901631
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28234803
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28472487
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=4243440
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=5215809
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=5764541
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=5870893
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=6057562
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=7927284
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=955389