Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:39:00 UTC
HMDB IDHMDB0000153
Secondary Accession Numbers
  • HMDB00153
Metabolite Identification
Common NameEstriol
DescriptionEstriol is a metabolite of estrone metabolized via 16alpha-hydroxyestrone through the enzyme 16alpha-hydroxysteroid dehydrogenase (EC 1.1.1.147) or to 2- or 4-hydroxyestrone (catechol estrogens) by the action of catecho-O-methyltransferase (EC 2.1.1.6). The latter metabolites can be formed in the brain and may compete with receptors for catecholamines. Metabolites are conjugated with sulfate or glucuronide before excretion by the kidney. During pregnancy, estriol constitutes 60-70% of the total estrogens, increasing to 300-500-fold in relation to non-pregnant women. The late term human fetus produces relatively large amounts of 16 alphahydroxy DHEA, which serves the mother as a precursor of estriol. It has been shown that 90% of the precursors for the formation of estriol are of fetal origin. If abnormal maternal serum screening results, specifically low levels of unconjugated estriol in the second trimester are detected, a diagnosis of Smith-Lemli-Opitz syndrome (SLOS),or RSH is suspected. SLOS is an autosomal recessive disorder caused by mutations of the gene encoding 7-dehydrocholesterol reductase (EC 1.3.1.21, DHCR7). (PMID: 16202579 , 16112271 , 16097001 ).
Structure
Data?1600201098
Synonyms
ValueSource
(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
13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triolHMDB
13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triolHMDB
16alpha-EstriolHMDB
16α-EstriolHMDB
3,16alpha,17beta-EstriolHMDB
3,16α,17β-EstriolHMDB
3,16α,17β-Trihydroxyestra-1,3,5(10)-trieneHMDB
EstriolHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
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
Traditional 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
CAS Registry Number50-27-1
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
InChI Identifier
InChI=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
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
  • 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point282 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.45HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.84631661259
DarkChem[M-H]-167.0931661259
AllCCS[M+H]+172.38332859911
AllCCS[M-H]-175.98832859911
DeepCCS[M-2H]-212.64230932474
DeepCCS[M+Na]+187.45630932474
AllCCS[M+H]+172.432859911
AllCCS[M+H-H2O]+169.132859911
AllCCS[M+NH4]+175.432859911
AllCCS[M+Na]+176.332859911
AllCCS[M-H]-176.032859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-175.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Estriol[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=C33943.9Standard polar33892256
Estriol[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=C32917.3Standard non polar33892256
Estriol[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=C32941.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Estriol,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O2789.2Semi standard non polar33892256
Estriol,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C2794.1Semi standard non polar33892256
Estriol,1TMS,isomer #3C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O2771.9Semi standard non polar33892256
Estriol,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O2842.9Semi standard non polar33892256
Estriol,2TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C2782.1Semi standard non polar33892256
Estriol,2TMS,isomer #3C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C2842.9Semi standard non polar33892256
Estriol,3TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C2907.4Semi standard non polar33892256
Estriol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O3065.1Semi standard non polar33892256
Estriol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C3081.3Semi standard non polar33892256
Estriol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O)[C@@H]2O3084.3Semi standard non polar33892256
Estriol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O3374.5Semi standard non polar33892256
Estriol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3303.1Semi standard non polar33892256
Estriol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C3391.4Semi standard non polar33892256
Estriol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C3664.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Estriol GC-MS (3 TMS)splash10-005a-1983000000-2f46d0d29b48132f76702014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estriol EI-B (Non-derivatized)splash10-000i-4970000000-1aa2bbf3f32fd687c37d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Estriol GC-MS (Non-derivatized)splash10-005a-1983000000-2f46d0d29b48132f76702017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1390000000-492aa66975c4e026b9d82017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estriol GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-3950000000-c2f0781bc5056d66aaf52014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-1900000000-1fab12be883127f80c672012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol EI-B (JEOL JMS-01-SG-2) , Positive-QTOFsplash10-000i-4970000000-1aa2bbf3f32fd687c37d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol Linear Ion Trap , negative-QTOFsplash10-000i-0390000000-891430228022fb330b422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 10V, Negative-QTOFsplash10-000i-0090000000-7ce66600861479086f4f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 40V, Negative-QTOFsplash10-000i-1970000000-6d5c77ab4f1744109b862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 20V, Negative-QTOFsplash10-000i-0090000000-331480c31f6585f70cf22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 10V, Positive-QTOFsplash10-0zg0-0590000000-6ee9bd7dbdbd777f46a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 40V, Positive-QTOFsplash10-0a4i-2900000000-d7ae7d481cc02d1ab8392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 20V, Positive-QTOFsplash10-0a4i-2920000000-d7d95b3d24e7be97e8482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Estriol 10V, Positive-QTOFsplash10-000i-0090000000-3aa436f48e23664bd4552021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 10V, Positive-QTOFsplash10-000i-0190000000-b047d204e97271aa8a652017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 20V, Positive-QTOFsplash10-00dr-0490000000-c0c0bd8b1dc1381c06fa2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 40V, Positive-QTOFsplash10-0ufr-3950000000-b7180dbe548021fd7fc92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 10V, Negative-QTOFsplash10-000i-0090000000-743915792d6f69593b2b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 20V, Negative-QTOFsplash10-000i-0090000000-8469d578b4631e8de9952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 40V, Negative-QTOFsplash10-02p0-0190000000-738399876b56d0e183d52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 20V, Negative-QTOFsplash10-00kr-0090000000-4e0854fb8be9cf34de972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 40V, Negative-QTOFsplash10-02br-0090000000-70686fa9219ae093945a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 10V, Positive-QTOFsplash10-000i-0090000000-1126a56061a8c854c7552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 20V, Positive-QTOFsplash10-0fga-0790000000-a1dba0b6195890b30d912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estriol 40V, Positive-QTOFsplash10-0a6v-3910000000-64d9abb8f215c1264e1f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Amniotic Fluid
  • Blood
  • Urine
Tissue Locations
  • Adrenal Cortex
  • Adrenal Gland
  • Kidney
  • Liver
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.0023 +/- 0.0007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.006 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000100 -0.00700 uMAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.001 +/- 0.00055 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.004 +/- 0.002 uMAdult (>18 years old)Both
Ambulant pregnancy
details
BloodDetected and Quantified0.205 +/- 0.04 uMAdult (>18 years old)Female
Diabetes
details
BloodDetected and Quantified<0.00000002 uMChildren (1-13 years old)Female
Aromatase deficiency
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [PubMed:2994907 ]
Diabetes mellitus type 2
  1. Giussi GA, Ballejo G, Benedetti WL: Estriol serum levels, neonatal vitality and stromal villous edema in diabetic pregnancies. Acta Diabetol Lat. 1979 Apr-Jun;16(2):105-10. [PubMed:484160 ]
Aromatase deficiency
  1. Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
Associated OMIM IDs
DrugBank IDDB04573
Phenol Explorer Compound IDNot Available
FooDB IDFDB006781
KNApSAcK IDNot Available
Chemspider ID5553
KEGG Compound IDC05141
BioCyc IDESTRIOL
BiGG ID45207
Wikipedia LinkEstriol
METLIN ID2581
PubChem Compound5756
PDB IDNot Available
ChEBI ID27974
Food Biomarker OntologyNot Available
VMH IDESTRIOL
MarkerDB IDMDB00000074
Good Scents IDNot Available
References
Synthesis ReferenceLeeds, Norma S.; Fukushima, David K.; Gallagher, T. F. Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol. Journal of the American Chemical Society (1954), 76 2943-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Diczfalusy E: The early history of estriol. J Steroid Biochem. 1984 Apr;20(4B):945-53. [PubMed:6374294 ]
  2. Kashork CD, Sutton VR, Fonda Allen JS, Schmidt DE, Likhite ML, Potocki L, O'Brien WE, Shaffer LG: Low or absent unconjugated estriol in pregnancy: an indicator for steroid sulfatase deficiency detectable by fluorescence in situ hybridization and biochemical analysis. Prenat Diagn. 2002 Nov;22(11):1028-32. [PubMed:12424769 ]
  3. Furuhashi N, Tsujiei M: [Clinical significance of serum and urinary estriol analysis in endocrine tests of the gonadal and placental system]. Nihon Rinsho. 1989 Dec;48 Suppl:1260-2. [PubMed:2621854 ]
  4. Ronin-Walknowska E, Szczygielski A, Skoczowska M: [Usefulness of determining free estriol, placental lactogen, progesterone, placental alkaline phosphatase, uric acid, hematocrit, hemoglobin and proteins in the blood and estrogen in the urine in the prognosis of the status of newborn infants in EPH gestosis]. Ginekol Pol. 1987 Jan;58(1):21-6. [PubMed:3583036 ]
  5. Fredricsson B, Carlstrom K, Eneroth P: Short-term variations in urinary estriol and renal function. Possible effects of extraneous conditions. Gynecol Obstet Invest. 1978;9(5):268-76. [PubMed:752645 ]
  6. Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [PubMed:2994907 ]
  7. Truran PL, Read GF, Walker S: Radioimmunoassay for salivary estriol, with use of an 125I radioligand and a solid-phase separation technique. Clin Chem. 1982 Dec;28(12):2393-7. [PubMed:7139918 ]
  8. Izumi H, Saito N, Ichiki S, Makino Y, Yukitake K, Kaneoka T: Prenatal diagnosis of congenital lipoid adrenal hyperplasia. Obstet Gynecol. 1993 May;81(5 ( Pt 2)):839-41. [PubMed:8469492 ]
  9. Guedeney X, Chanez C, Grenier A, Scherrmann JM: Temperature-dependent immunoreactive assay to screen for digoxin-like immunoreactive factor(s). Clin Chem. 1991 Nov;37(11):1900-4. [PubMed:1718632 ]
  10. Andreolini F, Di Corcia A, Lagana A, Samperi R, Raponi G: Preliminary isolation of urinary placental estriol before gas or liquid chromatography. Clin Chem. 1983 Dec;29(12):2076-8. [PubMed:6640903 ]
  11. Evans JJ, Wilkinson AR, Aickin DR: Salivary estriol concentrations during normal pregnancies, and a comparison with plasma estriol. Clin Chem. 1984 Jan;30(1):120-1. [PubMed:6690116 ]
  12. Kono H, Furuhashi N, Shinkawa O, Takahashi T, Tsujiei M, Yajima A: The maternal serum cortisol levels after onset of labor. Tohoku J Exp Med. 1987 Jun;152(2):133-7. [PubMed:3629582 ]
  13. Moore ML: Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women? MCN Am J Matern Child Nurs. 1999 Mar-Apr;24(2):80-6. [PubMed:10083784 ]
  14. Pentikainen PJ, Pentikainen LA, Azarnoff DL, Dujovne CA: Plasma levels and excretion of estrogens in urine in chronic lever disease. Gastroenterology. 1975 Jul;69(1):20-7. [PubMed:1171044 ]
  15. Nutman A, Freud E, Itzhaky D, Dolfin T, Tepper R: High maternal estriol level in pregnancy as a predictor of surgical intervention for undescended testis. Fertil Steril. 2005 Jul;84(1):249-52. [PubMed:16009196 ]
  16. Pasqualini JR: Enzymes involved in the formation and transformation of steroid hormones in the fetal and placental compartments. J Steroid Biochem Mol Biol. 2005 Dec;97(5):401-15. Epub 2005 Oct 3. [PubMed:16202579 ]
  17. Lardy H, Marwah A, Marwah P: C(19)-5-ene steroids in nature. Vitam Horm. 2005;71:263-99. [PubMed:16112271 ]
  18. Shinawi M, Szabo S, Popek E, Wassif CA, Porter FD, Potocki L: Recognition of Smith-Lemli-Opitz syndrome (RSH) in the fetus: utility of ultrasonography and biochemical analysis in pregnancies with low maternal serum estriol. Am J Med Genet A. 2005 Sep 15;138(1):56-60. [PubMed:16097001 ]
  19. Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. [PubMed:14634144 ]
  20. Trimesta [Link]

Only showing the first 10 proteins. There are 31 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:
HSD17B2
Uniprot ID:
P37059
Molecular weight:
42784.75
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular weight:
59215.8
References
  1. Mishra RG, Stanczyk FZ, Burry KA, Oparil S, Katzenellenbogen BS, Nealen ML, Katzenellenbogen JA, Hermsmeyer RK: Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H295-303. Epub 2005 Sep 30. [PubMed:16199482 ]
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Molecular weight:
26973.56
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
References
  1. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]

Only showing the first 10 proteins. There are 31 proteins in total.