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Showing Compound Etiocholanolone (FDB022072)

Record Information
Version1.0
Creation date2011-09-21 00:08:01 UTC
Update date2015-10-09 22:31:14 UTC
Primary IDFDB022072
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEtiocholanolone
DescriptionEtiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness). [HMDB]
CAS Number53-42-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3alpha,5beta)-3-Hydroxyandrostan-17-oneChEBI
3alpha-EtiocholanoloneChEBI
3alpha-Hydroxyetiocholan-17-oneChEBI
5-IsoandrosteroneChEBI
5beta-Androstan-3alpha-ol-17-oneChEBI
5beta-AndrosteroneChEBI
AETIOCHOLANOLONEChEBI
Etiocholan-3alpha-ol-17-oneChEBI
3alpha-Hydroxy-5beta-androstan-17-oneKegg
(3a,5b)-3-Hydroxyandrostan-17-oneGenerator
(3Α,5β)-3-hydroxyandrostan-17-oneGenerator
3a-EtiocholanoloneGenerator
3Α-etiocholanoloneGenerator
3a-Hydroxyetiocholan-17-oneGenerator
3Α-hydroxyetiocholan-17-oneGenerator
5b-Androstan-3a-ol-17-oneGenerator
5Β-androstan-3α-ol-17-oneGenerator
5b-AndrosteroneGenerator
5Β-androsteroneGenerator
Etiocholan-3a-ol-17-oneGenerator
Etiocholan-3α-ol-17-oneGenerator
3a-Hydroxy-5b-androstan-17-oneGenerator
3Α-hydroxy-5β-androstan-17-oneGenerator
3a-Hydroxy-5b-androstane-17-oneHMDB
5 beta AndrosteroneHMDB
5b-Androstane-3a-ol-17-oneHMDB
a-EtiocholanoloneHMDB
alpha-EtiocholanoloneHMDB
3-alpha-Hydroxy-5-beta-androstan-17-oneHMDB
5-beta-AndrosteroneHMDB
3 alpha Hydroxy 5 beta androstan 17 oneHMDB
(3α,5β)-3-hydroxyandrostan-17-oneGenerator
3α-etiocholanoloneGenerator
3α-hydroxy-5β-androstan-17-oneGenerator
3α-hydroxyetiocholan-17-oneGenerator
5β-androstan-3α-ol-17-oneGenerator
5β-androsteroneGenerator
Aetiocholanolonehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H30O2
IUPAC name(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
InChI IdentifierInChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
InChI KeyQGXBDMJGAMFCBF-BNSUEQOYSA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
Classification
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-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEtiocholanolone, non-derivatized, GC-MS Spectrumsplash10-052f-1890000000-943a0458e0d4232522f5Spectrum
GC-MSEtiocholanolone, non-derivatized, GC-MS Spectrumsplash10-052f-1890000000-943a0458e0d4232522f5Spectrum
Predicted GC-MSEtiocholanolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19aSpectrum
Predicted GC-MSEtiocholanolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7k-1139000000-2bff067a4137502d6ea7Spectrum
Predicted GC-MSEtiocholanolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEtiocholanolone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEtiocholanolone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEtiocholanolone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-052e-0090000000-976ebe75980115c6df372012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052k-4920000000-cd0699d57cde00089d272012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-6900000000-4cfdb3def9bc28b9a3392012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-052f-1890000000-7047f583d11b20a72f9b2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-42eb8c941695a061666d2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0290000000-1a37c17eb6ea7be9211c2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06u7-2790000000-d6e7cebd4af538181f772017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9e9f9de3b33af0311acd2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5ba62f51f815ded160022017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2190000000-513ad65531fff88b9f692017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-00c0e7de4e528b98df5c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-afb176951034ef62419f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052e-0930000000-1ed776267953f7acda8a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2900000000-1ba60805778f2942bfd72021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID5669
ChEMBL IDCHEMBL85799
KEGG Compound IDC04373
Pubchem Compound ID5880
Pubchem Substance IDNot Available
ChEBI ID28195
Phenol-Explorer IDNot Available
DrugBank IDDB02854
HMDB IDHMDB00490
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID43684
KNApSAcK IDNot Available
HET IDAE2
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEtiocholanolone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference