Record Information
Version1.0
Creation date2010-04-08 22:07:18 UTC
Update date2018-05-29 00:41:09 UTC
Primary IDFDB006781
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEstriol
DescriptionEstriol (also oestriol) is one of the three main estrogens produced by the human body. Estriol is found in common bean and pomegranate.
CAS Number50-27-1
Structure
Thumb
Synonyms
SynonymSource
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolChEBI
1,3,5(10)-Estratriene-3,16-alpha,17beta-triolChEBI
16alpha,17beta-EstriolChEBI
16alpha-HydroxyestradiolChEBI
3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratrieneChEBI
Deuslon-aChEBI
EstrielChEBI
OestriolChEBI
TrihydroxyestrinChEBI
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triolGenerator
(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triolGenerator
1,3,5(10)-Estratriene-3,16-a,17b-triolGenerator
1,3,5(10)-Estratriene-3,16-α,17β-triolGenerator
16a,17b-EstriolGenerator
16Α,17β-estriolGenerator
16a-HydroxyestradiolGenerator
16Α-hydroxyestradiolGenerator
3,16a,17b-Trihydroxy-delta(1,3,5)-estratrieneGenerator
3,16Α,17β-trihydroxy-δ(1,3,5)-estratrieneGenerator
3,16a,17b-Trihydroxy-δ(1,3,5)-estratrieneHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triolHMDB
16-alpha,17-beta-EstriolHMDB
16-alpha,17-beta-OestriolHMDB
16-alpha-HydroxyestradiolHMDB
16a-EstriolHMDB
16alpha,17beta-OestriolHMDB
16alpha-Hydroxy-17beta-estradiolHMDB
16alpha-HydroxyoestradiolHMDB
3,16a,17b-EstriolHMDB
3,16a,17b-Trihydroxyestra-1,3,5(10)-trieneHMDB
3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratrieneHMDB
3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-trieneHMDB
AacifemineHMDB
ColpogynHMDB
ColpovisterHMDB
DestriolHMDB
Deuslon aHMDB
Estra-1,3,5(10)-triene-3,16a,17b-triolHMDB
EstratriolHMDB
Follicular hormone hydrateHMDB
GynasanHMDB
HemostyptanonHMDB
Holin VHMDB
HormomedHMDB
IncurinHMDB
Klimax eHMDB
KlimoralHMDB
OekolpHMDB
OestratriolHMDB
OestriolumHMDB
OrestinHMDB
OrgastyptinHMDB
Ortho-gynestHMDB
OvesterinHMDB
OvestinHMDB
OvestinonHMDB
OvestrionHMDB
Ovo-vincesHMDB
TheelolHMDB
TridestrinHMDB
TriovexHMDB
16-alpha-Hydroxy-estradiolHMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
16beta Hydroxy estradiolHMDB
16beta-Hydroxy-estradiolHMDB
EpiestriolHMDB
16 alpha Hydroxy estradiolHMDB
16alpha,17beta EstriolHMDB
Estra-1,3,5(10)-triene-3,16beta,17beta-triolHMDB
(16α,17β)-Estra-1,3,5(10)-triene-3,16,17-triolbiospider
(16α,17β)-Oestra-1,3,5(10)-triene-3,16,17-triolbiospider
(16alpha,17beta)-Oestra-1,3,5(10)-triene-3,16,17-triolbiospider
(16α,17β)-estra-1,3,5(10)-triene-3,16,17-triolGenerator
1,3,5(10)-Estratrien-3,16α,17β-triolbiospider
1,3,5(10)-Estratriene-3,16,17-Triolbiospider
1,3,5(10)-Estratriene-3,16α,17β-Triolbiospider
1,3,5(10)-Estratriene-3,16alpha,17beta-triolbiospider
16-alpha-Hydroxyoestradiolbiospider
16-hydroxyestradiolbiospider
16α-Estriolbiospider
16α-Hydroxy-17β-estradiolbiospider
16α-Hydroxyestradiolbiospider
16α-Hydroxyoestradiolbiospider
16α,17β-Estriolbiospider
16α,17β-Oestriolbiospider
16α-hydroxyestradiolGenerator
3,16-α,17-β-Oestriolbiospider
3,16-α,17-β-Trihydroxyoestra-1,3,5(10)-trienebiospider
3,16-alpha,17-beta-Estriolbiospider
3,16-alpha,17-beta-Oestriolbiospider
3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-estratrienebiospider
3,16-alpha,17-beta-Trihydroxy-delta-1,3,5-oestratrienebiospider
3,16-alpha,17-beta-Trihydroxyestra-1,3,5(10)-trienebiospider
3,16-alpha,17-beta-Trihydroxyoestra-1,3,5(10)-trienebiospider
3,16α,17β-Estriolbiospider
3,16α,17β-Trihydroxy-1,3,5(10)-estratrienebiospider
3,16α,17β-Trihydroxyestra-1,3,5(10)-trienebiospider
3,16alpha,17beta-Estriolbiospider
3,16α,17β-trihydroxy-δ(1,3,5)-estratrieneGenerator
Estra-1,3,5(10)-trien-3,16α,17β-triolbiospider
Estra-1,3,5(10)-trien-3,16alpha,17beta-triolbiospider
Estra-1,3,5(10)-triene-3,16,17-triol, (16α,17β)-biospider
Estra-1,3,5(10)-triene-3,16,17-triol, (16alpha,17beta)-biospider
Estra-1,3,5(10)-triene-3,16α,17β-triolbiospider
Estra-1,3,5(10)-triene-3,16alpha,17beta-triolbiospider
Estriolmanual
Gynaesanbiospider
Holin vbiospider
Oestra-1,3,5(10)-triene-3,16-alpha,17-beta-triolbiospider
Oestra-1,3,5(10)-triene-3,16α, 17β-triolbiospider
Oestra-1,3,5(10)-triene-3,16alpha,17beta-triolbiospider
ortho-GynestHMDB
Overstinbiospider
Trihydroxyoestrinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.54ALOGPS
logP2.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m³·mol⁻¹ChemAxon
Polarizability33.08 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H24O3
IUPAC name(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol
InChI IdentifierInChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
InChI KeyPROQIPRRNZUXQM-ZXXIGWHRSA-N
Isomeric SMILES[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
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
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point282 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.45HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-005a-1983000000-2f46d0d29b48132f7670View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4970000000-1aa2bbf3f32fd687c37dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005a-1983000000-2f46d0d29b48132f7670View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1390000000-492aa66975c4e026b9d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-1900000000-1fab12be883127f80c67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-000i-4970000000-1aa2bbf3f32fd687c37dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0390000000-891430228022fb330b42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-b047d204e97271aa8a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0490000000-c0c0bd8b1dc1381c06faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3950000000-b7180dbe548021fd7fc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-743915792d6f69593b2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-8469d578b4631e8de995View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02p0-0190000000-738399876b56d0e183d5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-3950000000-c2f0781bc5056d66aaf5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5553
ChEMBL IDCHEMBL193482
KEGG Compound IDC05141
Pubchem Compound ID5756
Pubchem Substance IDNot Available
ChEBI ID27974
Phenol-Explorer IDNot Available
DrugBank IDDB04573
HMDB IDHMDB00153
CRC / DFC (Dictionary of Food Compounds) IDGQH02-E:GQH02-E
EAFUS IDNot Available
Dr. Duke IDESTRIOL|ESTROL
BIGG ID45207
KNApSAcK IDNot Available
HET IDESL
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEstriol
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
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hot-flashDUKE
anti menopausal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
estrogenicDUKE
transdermalDUKE
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
Estrogen receptorESR1P03372
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
PathwaysNot Available
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).