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Estradiol (FDB000362)

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 beta-estradiol, 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-075a-2920000000-10218bfa5b56f829853e2014-09-20View Spectrum
GC-MSEstradiol, 2 TMS, GC-MS Spectrumsplash10-017r-1791100000-7b16254894cdcb8ee86dSpectrum
GC-MSEstradiol, non-derivatized, GC-MS Spectrumsplash10-00di-1980000000-b2dec84718861de189ecSpectrum
GC-MSEstradiol, non-derivatized, GC-MS Spectrumsplash10-00di-3940000000-f3692a81f624f15d3e0bSpectrum
GC-MSEstradiol, non-derivatized, GC-MS Spectrumsplash10-00di-0960000000-be4e96105398cb805cd9Spectrum
GC-MSEstradiol, non-derivatized, GC-MS Spectrumsplash10-00di-0790000000-5c858378c15135811824Spectrum
GC-MSEstradiol, non-derivatized, GC-MS Spectrumsplash10-017r-1791100000-7b16254894cdcb8ee86dSpectrum
Predicted GC-MSEstradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de4Spectrum
Predicted GC-MSEstradiol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b5160Spectrum
Predicted GC-MSEstradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstradiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstradiol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstradiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstradiol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstradiol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0590000000-1dd83cbcb3d21edfbdbd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-f3279d6cdab9cf3800fd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-0efe28378f612aab8c3d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-00di-1980000000-b2dec84718861de189ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-00di-3940000000-f3692a81f624f15d3e0b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-00di-0960000000-be4e96105398cb805cd92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-0790000000-5c83456da6e28375ad512012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0490000000-c3c4658cfae36bedff302017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-d2ee002f4c0363c04e832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0960000000-2ad7c6e17386448419df2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-f73a7a19d55a4f78be012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-2900000000-a22a9233ffbb9eb05a1b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4i-1900000000-51d28e077b0aefa6aa1c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-002b-0930000000-c177eb564c729479f2be2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0190000000-b572b380a16bb1b20b272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-0960000000-d2ee002f4c0363c04e832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-f906ca4989738e61667a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0190000000-2924fb687c668eb8918a2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-53eccf4b813f6992d38d2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6890000000-c399a267a752cfdba3232017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-274ccc6305612709fd332017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-afc94cc62691bfb341612017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0190000000-8d49a19142b1bd1a09a12017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
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).