Record Information
Version1.0
Creation date2010-04-08 22:04:32 UTC
Update date2019-11-26 02:54:40 UTC
Primary IDFDB000362
Secondary Accession Numbers
  • FDB030279
Chemical Information
FooDB NameEstradiol
DescriptionEstradiol, also known as estradiol-17beta or progynon, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estradiol is considered to be a steroid lipid molecule. Estradiol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estradiol is a potentially toxic compound.
CAS Number50-28-2
Structure
Thumb
Synonyms
SynonymSource
(17beta)-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta OestradiolChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta-OestradiolChEBI
beta-EstradiolChEBI
cis-EstradiolChEBI
Estradiol-17betaChEBI
ClimaraKegg
DivigelKegg
EstraceKegg
EstradermKegg
EstrasorbKegg
EstringKegg
EstrogelKegg
InnofemKegg
VagifemKegg
VivelleKegg
(17b)-Estra-1,3,5(10)-triene-3,17-diolGenerator
(17Β)-estra-1,3,5(10)-triene-3,17-diolGenerator
17b OestradiolGenerator
17Β oestradiolGenerator
17b-Estra-1,3,5(10)-triene-3,17-diolGenerator
17Β-estra-1,3,5(10)-triene-3,17-diolGenerator
17b-OestradiolGenerator
17Β-oestradiolGenerator
b-EstradiolGenerator
Β-estradiolGenerator
Estradiol-17bGenerator
Estradiol-17βGenerator
(+)-3,17b-EstradiolHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-olHMDB
17b-EstradiolHMDB
3,17-EpidihydroxyestratrieneHMDB
3,17b-Dihydroxyestra-1,3,5(10)-trieneHMDB
3,17b-EstradiolHMDB
AerodiolHMDB
AgofollinHMDB
AltradHMDB
AmnestrogenHMDB
AquadiolHMDB
BardiolHMDB
ClimadermHMDB
CompudoseHMDB
CorpagenHMDB
D-EstradiolHMDB
D-OestradiolHMDB
delta-EstradiolHMDB
delta-OestradiolHMDB
DermestrilHMDB
Dihydro-theelinHMDB
Dihydrofollicular hormoneHMDB
DihydrofolliculinHMDB
DihydromenformonHMDB
DihydrotheelinHMDB
DihydroxyestrinHMDB
DimenformonHMDB
DiogynHMDB
DiogynetsHMDB
EncoreHMDB
Epiestriol 50HMDB
Estra-1,3,5(10)-triene-3,17b-diolHMDB
Estraderm TTSHMDB
Estradiol-17-betaHMDB
EstradotHMDB
EstraldineHMDB
Estring vaginal ringHMDB
EstroclimHMDB
Estroclim 50HMDB
Estrogel HBFHMDB
EstroviteHMDB
EvorelHMDB
FemestralHMDB
FemogenHMDB
FollicyclinHMDB
GelestraHMDB
GinosedolHMDB
GynergonHMDB
GynoestrylHMDB
LamdiolHMDB
MacrodiolHMDB
MenorestHMDB
NordicolHMDB
OesclimHMDB
OestergonHMDB
Oestra-1,3,5(10)-triene-3,17b-diolHMDB
OestradiolHMDB
OestrogelHMDB
OestroglandolHMDB
OvahormonHMDB
OvasterolHMDB
OvastevolHMDB
OvocyclinHMDB
OvocylinHMDB
PerlatanolHMDB
PrimofolHMDB
ProfoliolHMDB
Profoliol bHMDB
ProgynonHMDB
Progynon DHHMDB
Sandrena 1HMDB
SyndiolHMDB
SystenHMDB
ZumenonHMDB
Estradiol hemihydrate, (17 alpha)-isomerHMDB
Estradiol, (-)-isomerHMDB
Estradiol, monosodium saltHMDB
Estradiol-17 betaHMDB
17 beta OestradiolHMDB
17 beta-EstradiolHMDB
Estradiol 17 betaHMDB
Estradiol monohydrateHMDB
Estradiol orion brandHMDB
Estradiol, (17-alpha)-isomerHMDB
Estradiol, sodium saltHMDB
17 beta EstradiolHMDB
Estradiol hemihydrateHMDB
Estradiol, (+-)-isomerHMDB
Estradiol, (16 alpha,17 alpha)-isomerHMDB
Estradiol-17 alphaHMDB
Orion brand OF estradiolHMDB
17 beta-OestradiolHMDB
Estradiol 17 alphaHMDB
Estradiol 17betaHMDB
Estradiol anhydrousHMDB
Estradiol, (16 alpha,17 beta)-isomerHMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomerHMDB
Estradiol, (8 alpha,17 beta)-isomerHMDB
Estradiol, (9 beta,17 alpha)-isomerHMDB
Estradiol, (9 beta,17 beta)-isomerHMDB
Novartis pharmaceuticals brand OF estradiolHMDB
ProgynovaHMDB
Estradiol valerianteHMDB
Estradiol valerateHMDB
DelestrogenHMDB
Progynon depotHMDB
Progynon-depotHMDB
EstradiolChEBI
(+)-3,17beta-Estradiolbiospider
(17beta)-Estra-1(10),2,4-triene-3,17-diolbiospider
(17β)-estra-1,3,5(10)-triene-3,17-diolGenerator
1,3,5-Estratriene-3,17-beta-diolbiospider
1,3,5-Estratriene-3,17β-diolbiospider
1,3,5,(10)-Estratrien-3,17β-diolbiospider
17-beta-Estra-1,3,5(10)-triene-3,17-diolbiospider
17-beta-Estradiolbiospider
17-beta-Oestra-1,3,5(10)-triene-3,17-diolbiospider
17-beta-OH-Estradiolbiospider
17-beta-OH-Oestradiolbiospider
17β-Estra-1,3,5(10)-triene-3,17-diolbiospider
17β-Estradiolbiospider
17β-Oestra-1,3,5(10)-triene-3,17-diolbiospider
17β-Oestradiolbiospider
17beta-Estradiolbiospider
17beta-Oestra-1,3,5(10)-triene-3,17-diolbiospider
17β oestradiolGenerator
17β-estra-1,3,5(10)-triene-3,17-diolGenerator
17β-estradiolGenerator
17β-oestradiolGenerator
3,17-β-Oestradiolbiospider
3,17-beta-Dihydroxy-1,3,5(10)-oestratrienebiospider
3,17-beta-Dihydroxyestra-1,3,5(10)-trienebiospider
3,17-beta-Dihydroxyoestra-1,3,5-trienebiospider
3,17-beta-Estradiolbiospider
3,17-beta-Oestradiolbiospider
3,17β-Dihydroxy-1, 3,5(10)-oestratrienebiospider
3,17β-Dihydroxy-1,3,5(10)-estratrienebiospider
3,17β-Dihydroxy-1,3,5(10)-oestratrienebiospider
3,17β-Dihydroxyestra-1,3,5-trienebiospider
3,17β-Dihydroxyestra-1,3,5(10)-trienebiospider
3,17β-Dihydroxyoestra-1,3,5-trienebiospider
3,17β-Estradiolbiospider
3,17beta-Dihydroxyestra-1,3,5-trienebiospider
3,17beta-Dihydroxyestra-1,3,5(10)-trienebiospider
3,17beta-Dihydroxyoestra-1,3,5-trienebiospider
3,17beta-Estradiolbiospider
cis-Oestradiolbiospider
D-3,17-beta-Estradiolbiospider
D-3,17-beta-Oestradiolbiospider
D-3,17β-Estradiolbiospider
D-3,17β-Oestradiolbiospider
D-3,17beta-Estradiolbiospider
D-3,17beta-Oestradiolbiospider
dihydro-TheelinHMDB
Estraderm ttsHMDB
Estradiol, INN, USANdb_source
Estrogel hbfHMDB
Oestra-1,3,5(10)-triene-3,17-beta-diolbiospider
Oestra-1,3,5(10)-triene-3,17β-diolbiospider
Oestra-1,3,5(10)-triene-3,17beta-diolbiospider
Oestradiol, BANdb_source
Progynon dhHMDB
β-estradiolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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
Polarizability32.12 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H24O2
IUPAC name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
InChI IdentifierInChI=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-ZBRFXRBCSA-N
Isomeric 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
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.37%; H 8.88%; O 11.75%DFC
Melting PointMp 178°DFC
Boiling PointNot Available
Experimental Water Solubility0.0036 mg/mL at 27 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP4.01HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical Rotation[a]18D +78 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-017r-1791100000-7b16254894cdcb8ee86dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1980000000-b2dec84718861de189ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-3940000000-f3692a81f624f15d3e0bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0960000000-be4e96105398cb805cd9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0790000000-5c858378c15135811824JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017r-1791100000-7b16254894cdcb8ee86dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b5160JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0590000000-1dd83cbcb3d21edfbdbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-f3279d6cdab9cf3800fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-0efe28378f612aab8c3dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-00di-1980000000-b2dec84718861de189ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-00di-3940000000-f3692a81f624f15d3e0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00di-0960000000-be4e96105398cb805cd9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-0790000000-5c83456da6e28375ad51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0490000000-c3c4658cfae36bedff30JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-d2ee002f4c0363c04e83JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-2ad7c6e17386448419dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0190000000-2924fb687c668eb8918aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-53eccf4b813f6992d38dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6890000000-c399a267a752cfdba323JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-274ccc6305612709fd33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-afc94cc62691bfb34161JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0190000000-8d49a19142b1bd1a09a1JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-075a-2920000000-10218bfa5b56f829853eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID5554
ChEMBL IDCHEMBL135
KEGG Compound IDC00951
Pubchem Compound ID5757
Pubchem Substance IDNot Available
ChEBI ID16469
Phenol-Explorer IDNot Available
DrugBank IDDB00783
HMDB IDHMDB00151
CRC / DFC (Dictionary of Food Compounds) IDBBB24-E:BBB29-J
EAFUS IDNot Available
Dr. Duke IDESTRADIOL|17-BETA-ESTRADIOL|ESTRADIOL-17-BETA
BIGG ID36456
KNApSAcK IDNot Available
HET IDEST
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEstradiol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
estrogenicDUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
Estrogen receptor betaESR2Q92731
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
Sex hormone-binding globulinSHBGP04278
Nuclear receptor subfamily 1 group I member 2NR1I2O75469
Estrogen receptorESR1P03372
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).