Showing metabocard for 17a-Estradiol (BMDB0000429)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:36 UTC
Update Date2020-06-04 20:43:46 UTC
MCDB ID BMDB0000429
Secondary Accession Numbers
  • BMDB00429
Metabolite Identification
Common Name17a-Estradiol
Description17a-Estradiol, also known as alpha-estradiol or estradiol-17alpha, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 17a-estradiol is considered to be a steroid lipid molecule. 17a-Estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-Estradiol is a potentially toxic compound. 17a-Estradiol has been linked to the inborn metabolic disorders including glutaryl-coa dehydrogenase deficiency (gdhd).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AlfatradiolChEBI
alpha-EstradiolChEBI
Estra-1,3,5(10)trien-3,17alpha-diolChEBI
Estradiol-17alphaChEBI
a-EstradiolGenerator
Α-estradiolGenerator
Estra-1,3,5(10)trien-3,17a-diolGenerator
Estra-1,3,5(10)trien-3,17α-diolGenerator
Estradiol-17aGenerator
Estradiol-17αGenerator
17a-EstradiolGenerator
17Α-estradiolGenerator
1,3,5-Estratriene-3,17a-diolHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diolHMDB
17-EpiestradiolHMDB
17a-OestradiolHMDB
3,17-DihydroxyestratrieneHMDB
3,17a-Dihydroxyestra-1,3,5(10)-trieneHMDB
3,17a-Dihydroxyoestra-1,3,5(10)-trieneHMDB
EpiestradiolHMDB
EpiestrolHMDB
Estra-1,3,5(10)-triene-3,17a-diolHMDB
Oestra-1,3,5(10)-triene-3,17a-diolHMDB
17alpha-EstradiolKEGG
Chemical FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
IUPAC Name(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
Traditional Name(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
CAS Registry Number57-91-0
SMILES
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
InChI Identifier
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
InChI KeyVOXZDWNPVJITMN-SFFUCWETSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point216 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0039 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.57ALOGPS
logP3.75ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m³·mol⁻¹ChemAxon
Polarizability31.93 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00p0-3970000000-ea6c869f7a3556f5fb552014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00p0-3970000000-ea6c869f7a3556f5fb552017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b51602017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-1ba1e242ed699b46bf672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-7900000000-0dae6df990a37c6c3fb32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-956bcdeac1a836c6b83c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0190000000-452a42851493e9ce5c802021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0690000000-71ce13a2bfc9d4213bb72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0090000000-2f90ef030c1d0edf8ad02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-abcf1c18fabe5707d6dd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004j-0930000000-a22a631636419abce8d12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a3dd3e1428abd9a336042021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00dj-0690000000-8ffd5ef2044d03b467202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-7155e44ebc26fe65b9012021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0090000000-86e488508b64b443756f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0690000000-2e46725f97f4019883a52021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0090000000-6ced41e08d82a4b046302017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-4d9df1569ae5699676942017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004u-4690000000-661cc510ebfd4c2a24652017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d0a3fa240c972ee299db2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-5e0ebfacd0ec2ed930f52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0090000000-da2f1bf0efabdae031882017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-75c81b9a2f86b3e98ca72021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i1-0690000000-f9708f269ca012832fdc2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dj-3910000000-ae2ec96914444b71ca582021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-fb43b1971567fc332aa72021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-28ae91cf9a3f37856adb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-325f0a631253fd5784bb2021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-2950000000-9cd3211b8fd922d6f32b2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0002 +/- 0.00004 uM details
Detected and Quantified0.00011 uM details
Detected and Quantified0.00012 uM details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000429
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112198
KNApSAcK IDNot Available
Chemspider ID61840
KEGG Compound IDC02537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link17α-Estradiol
METLIN ID5418
PubChem Compound68570
PDB IDNot Available
ChEBI ID17160
References
Synthesis ReferenceGardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
  2. Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. [PubMed:18214159 ]
  3. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
  4. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]