Epimetendiol (CHEM036016)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:33 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036016
Identification
Common NameEpimetendiol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3a,5b,17a)-17-Methyl-androst-1-ene-3,17-diolHMDB
17-EpimetendiolHMDB
17b-Methyl-5b-androst-1-ene-3a,17a-diolHMDB
Chemical FormulaC21H34O2
Average Molecular Mass318.494 g/mol
Monoisotopic Mass318.256 g/mol
CAS Registry Number132830-78-5
IUPAC Name(1S,2R,5S,7R,10R,11S,14R,15S)-2,7,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-5,14-diol
Traditional Name(1S,2R,5S,7R,10R,11S,14R,15S)-2,7,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-5,14-diol
SMILES[H][C@@]12CC[C@@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2(C)C[C@H](O)C=C[C@]12C
InChI IdentifierInChI=1S/C21H34O2/c1-18-9-6-15-16(19(18,2)10-5-14(22)13-18)7-11-20(3)17(15)8-12-21(20,4)23/h5,10,14-17,22-23H,6-9,11-13H2,1-4H3/t14-,15-,16+,17+,18-,19-,20+,21-/m1/s1
InChI KeyNZDUEHZAWOAARB-BWTDTTKRSA-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
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-1-steroid
  • Delta-1-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.003 g/LALOGPS
logP4.2ALOGPS
logP3.58ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)17.82ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.71 m³·mol⁻¹ChemAxon
Polarizability38.03 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0394000000-550212ab13569642c1f3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-3136900000-d40337e4da1bc1df9b8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0029000000-fc9865121ee7b1a49766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0396000000-23faa0a0e0e8a98a21d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-2790000000-72b932c273db57d4e4f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-87ba1293bec3050192f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0079000000-ec3aee49be5fc73a2c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uki-0193000000-82cef7e42d20d19603baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0069000000-ca491da3e19bbe899e4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-2921000000-f33041070d4a0d36b605Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2900000000-729e8a52c9b9a279d0e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0039000000-7eb484efeb5b1fc04f1bSpectrum
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 IDHMDB0006012
FooDB IDFDB023801
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477798
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kokkonen J, Leinonen A, Tuominen J, Seppala T: Comparison of sensitivity between gas chromatography-low-resolution mass spectrometry and gas chromatography-high-resolution mass spectrometry for determining metandienone metabolites in urine. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):179-89.
2. Schanzer W, Geyer H, Fussholler G, Halatcheva N, Kohler M, Parr MK, Guddat S, Thomas A, Thevis M: Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine. Rapid Commun Mass Spectrom. 2006;20(15):2252-8.
3. Habscheid W, Abele U, Dahm HH: [Severe cholestasis with kidney failure from anabolic steroids in a body builder]. Dtsch Med Wochenschr. 1999 Sep 10;124(36):1029-32.
4. Fedorov IV: [Biochemical changes in skeletal muscles during hypokinesia and possible means for counteracting them]. Kosm Biol Aviakosm Med. 1975 Jan-Feb;9(1):3-8.
5. LARON Z, GITTER S: ANABOLIC STEROIDS: THEIR CLINICAL USE AND SPECIFIC DANGERS IN PEDIATRICS. Clin Pediatr (Phila). 1963 Nov;2:594-600.
6. TAINTER ML, ARNOLD A, BEYLER AL, POTTS GO, ROTH CH: ANABOLIC STEROIDS IN THE MANAGEMENT OF THE DIABETIC PATIENT. N Y State J Med. 1964 Apr 15;64:1001-9.
7. Pope HG Jr, Katz DL: Affective and psychotic symptoms associated with anabolic steroid use. Am J Psychiatry. 1988 Apr;145(4):487-90.
8. Moldawer M: Anabolic agents: clinical efficacy versus side effects. J Am Med Womens Assoc. 1968 Apr;23(4):352-69.
9. Herbst AL: Exogenous hormones in pregnancy. Clin Obstet Gynecol. 1973 Dec;16(4):37-50.
10. Hirst AE Jr, Gore I: Marfan's syndrome: a review. Prog Cardiovasc Dis. 1973 Sep-Oct;16(2):187-98.
11. Adigamov LF, Nesterin MF: [Metabolism of hormonal growth stimulants and chemical methods for determining them (a review of the literature)]. Vopr Pitan. 1973 Nov-Dec;(6):43-50.
12. Zharov EI, Segal' RG: [Use of anabolic hormones for the treatment of cardiovascular patients]. Kardiologiia. 1969 Jan;9(1):144-53.
13. Marks V, Salmols E: [Glucagon mediated insulin release in man]. Acta Diabetol Lat. 1968 Oct;5 Suppl 1:285-308.
14. Mossor-Ostrowska J: [Anabolic steroids in the treatment of liver diseases]. Pol Tyg Lek. 1971 Aug 9;26(32):1248-51.
15. Badalian LO, Temin PA, Mukhin KIu: [Treatment problems using anabolic steroids in progressive muscular dystrophy]. Klin Med (Mosk). 1984 Nov;62(11):23-9.