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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:07 UTC
HMDB IDHMDB00153
Secondary Accession NumbersNone
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
Thumb
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-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-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)-estratrieneGenerator
16a,17b-EstriolHMDB
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-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
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
Traditional Nameestriol
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 KeyInChIKey=PROQIPRRNZUXQM-ZXXIGWHRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point282 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability33.07 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-005a-1983000000-2f46d0d29b48132f7670View 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
MSMass Spectrum (Electron Ionization)splash10-000i-3950000000-c2f0781bc5056d66aaf5View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Urine
Tissue Location
  • Adrenal Cortex
  • Adrenal Gland
  • Kidney
  • Liver
  • Placenta
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified0.001 +/- 0.00055 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
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. [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. [484160 ]
Associated OMIM IDs
DrugBank IDDB04573
DrugBank Metabolite IDDBMET00492
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB006781
KNApSAcK IDNot Available
Chemspider ID5553
KEGG Compound IDC05141
BioCyc IDNot Available
BiGG ID45207
Wikipedia LinkEstriol
NuGOwiki LinkHMDB00153
Metagene LinkHMDB00153
METLIN ID2581
PubChem Compound5756
PDB IDESL
ChEBI ID27974
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. [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. [12424769 ]
  3. Furuhashi N, Tsujiei M: [Clinical significance of serum and urinary estriol analysis in endocrine tests of the gonadal and placental system] Nippon Rinsho. 1989 Dec;48 Suppl:1260-2. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [16202579 ]
  17. Lardy H, Marwah A, Marwah P: C(19)-5-ene steroids in nature. Vitam Horm. 2005;71:263-99. [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. [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. [14634144 ]
  20. Trimesta [Link]

Enzymes

General function:
Involved in estradiol 17-beta-dehydrogenase activity
Specific function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular weight:
34949.715
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:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B11
Uniprot ID:
O75310
Molecular weight:
61037.8
Reactions
Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
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:
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
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 transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Molecular weight:
59809.1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6
Molecular weight:
59741.0
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A7
Uniprot ID:
Q5DSZ7
Molecular weight:
59818.3
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 has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
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:
UGT1A5
Uniprot ID:
P35504
Molecular weight:
60070.565
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 has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
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. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
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:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
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 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:
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:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915
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 (By similarity).
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Molecular weight:
60253.94
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. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
References
  1. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [2011412 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
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 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 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. [16199482 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Molecular weight:
34323.875
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids.
Gene Name:
HSD17B6
Uniprot ID:
O14756
Molecular weight:
35965.41
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:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular weight:
59809.075
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:
UGT1A7
Uniprot ID:
Q9HAW7
Molecular weight:
59818.315
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:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
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.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
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. [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. [8779894 ]