ContaminantDB: Estriol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:42 UTC

Update Date

2026-03-31 17:33:10 UTC

Accession Number

CHEM003747

Identification

Common Name

Estriol

Class

Small Molecule

Description

A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Drug
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	ChEBI
1,3,5(10)-Estratriene-3,16-alpha,17beta-triol	ChEBI
16alpha,17beta-Estriol	ChEBI
16alpha-Hydroxyestradiol	ChEBI
3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratriene	ChEBI
Deuslon-a	ChEBI
Estriel	ChEBI
Oestriol	ChEBI
Trihydroxyestrin	ChEBI
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol	Generator
(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triol	Generator
1,3,5(10)-Estratriene-3,16-a,17b-triol	Generator
1,3,5(10)-Estratriene-3,16-α,17β-triol	Generator
16a,17b-Estriol	Generator
16Α,17β-estriol	Generator
16a-Hydroxyestradiol	Generator
16Α-hydroxyestradiol	Generator
3,16a,17b-Trihydroxy-delta(1,3,5)-estratriene	Generator
3,16Α,17β-trihydroxy-δ(1,3,5)-estratriene	Generator
3,16a,17b-Trihydroxy-δ(1,3,5)-estratriene	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol	HMDB
16-alpha,17-beta-Estriol	HMDB
16-alpha,17-beta-Oestriol	HMDB
16-alpha-Hydroxyestradiol	HMDB
16a-Estriol	HMDB
16alpha,17beta-Oestriol	HMDB
16alpha-Hydroxy-17beta-estradiol	HMDB
16alpha-Hydroxyoestradiol	HMDB
3,16a,17b-Estriol	HMDB
3,16a,17b-Trihydroxyestra-1,3,5(10)-triene	HMDB
3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene	HMDB
3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene	HMDB
Aacifemine	HMDB
Colpogyn	HMDB
Colpovister	HMDB
Destriol	HMDB
Deuslon a	HMDB
Estra-1,3,5(10)-triene-3,16a,17b-triol	HMDB
Estratriol	HMDB
Follicular hormone hydrate	HMDB
Gynasan	HMDB
Hemostyptanon	HMDB
Holin V	HMDB
Hormomed	HMDB
Incurin	HMDB
Klimax e	HMDB
Klimoral	HMDB
Oekolp	HMDB
Oestratriol	HMDB
Oestriolum	HMDB
Orestin	HMDB
Orgastyptin	HMDB
Ortho-gynest	HMDB
Ovesterin	HMDB
Ovestin	HMDB
Ovestinon	HMDB
Ovestrion	HMDB
Ovo-vinces	HMDB
Theelol	HMDB
Tridestrin	HMDB
Triovex	HMDB
16-alpha-Hydroxy-estradiol	HMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	HMDB
16beta Hydroxy estradiol	HMDB
16beta-Hydroxy-estradiol	HMDB
Epiestriol	HMDB
16 alpha Hydroxy estradiol	HMDB
16alpha,17beta Estriol	HMDB
Estra-1,3,5(10)-triene-3,16beta,17beta-triol	HMDB
13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triol	HMDB
13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triol	HMDB
16alpha-Estriol	HMDB
16α-Estriol	HMDB
3,16alpha,17beta-Estriol	HMDB
3,16α,17β-Estriol	HMDB
3,16α,17β-Trihydroxyestra-1,3,5(10)-triene	HMDB
Estriol	HMDB

Chemical Formula

C₁₈H₂₄O₃

Average Molecular Mass

288.381 g/mol

Monoisotopic Mass

288.173 g/mol

CAS Registry Number

50-27-1

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

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 Key

PROQIPRRNZUXQM-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens 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 Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:27974 )
3-hydroxy steroid (CHEBI:27974 )
16alpha-hydroxy steroid (CHEBI:27974 )
C18 steroids (estrogens) and derivatives (C05141 )
Estrane and derivatives (C05141 )
Estrogens (C05141 )
C18 steroids (estrogens) and derivatives (LMST02010003 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adrenal Cortex
Adrenal Gland
Kidney
Liver
Placenta
Testes

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	82-86°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.27 m³·mol⁻¹	ChemAxon
Polarizability	33.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-005a-1983000000-2f46d0d29b48132f7670	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005a-1983000000-2f46d0d29b48132f7670	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1390000000-492aa66975c4e026b9d8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-009i-2033900000-46c301a46b654b6c6bf3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-1900000000-1fab12be883127f80c67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0390000000-891430228022fb330b42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7ce66600861479086f4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1970000000-6d5c77ab4f1744109b86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-331480c31f6585f70cf2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0zg0-0590000000-6ee9bd7dbdbd777f46a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-d7ae7d481cc02d1ab839	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2920000000-d7d95b3d24e7be97e848	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-3aa436f48e23664bd455	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-b047d204e97271aa8a65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0490000000-c0c0bd8b1dc1381c06fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3950000000-b7180dbe548021fd7fc9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-743915792d6f69593b2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-8469d578b4631e8de995	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02p0-0190000000-738399876b56d0e183d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-843a74fabb1d0eb512a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0090000000-4e0854fb8be9cf34de97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02br-0090000000-70686fa9219ae093945a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-1126a56061a8c854c755	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fga-0790000000-a1dba0b6195890b30d91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6v-3910000000-64d9abb8f215c1264e1f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-3950000000-c2f0781bc5056d66aaf5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estriol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.

Metabolism

Not Available

Toxicity Values

ORAL (LD50): Acute: >2000 mg/kg [Rat].

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used as a test to determine the general health of an unborn fetus.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB04573

HMDB ID

HMDB0000153

FooDB ID

FDB006781

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

45207

BioCyc ID

ESTRIOL

METLIN ID

2581

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

James V. Freeman, Gary M. Johnson, “Synthesis of 6.alpha.-functionalized estriol haptens and protein conjugates thereof.” U.S. Patent US5902888, issued June, 1973.

MSDS

Link

General References

1. Leeds, 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.

2. Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.

3. Leeds, 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.

4. Diczfalusy E: The early history of estriol. J Steroid Biochem. 1984 Apr;20(4B):945-53.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.