ContaminantDB: 17a-Estradiol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:18:22 UTC

Update Date

2026-04-05 15:31:20 UTC

Accession Number

CHEM003788

Identification

Common Name

17a-Estradiol

Class

Small Molecule

Description

17a-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.

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
Alfatradiol	ChEBI
alpha-Estradiol	ChEBI
Estra-1,3,5(10)trien-3,17alpha-diol	ChEBI
Estradiol-17alpha	ChEBI
a-Estradiol	Generator
Α-estradiol	Generator
Estra-1,3,5(10)trien-3,17a-diol	Generator
Estra-1,3,5(10)trien-3,17α-diol	Generator
Estradiol-17a	Generator
Estradiol-17α	Generator
17a-Estradiol	Generator
17Α-estradiol	Generator
1,3,5-Estratriene-3,17a-diol	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol	HMDB
17-Epiestradiol	HMDB
17a-Oestradiol	HMDB
3,17-Dihydroxyestratriene	HMDB
3,17a-Dihydroxyestra-1,3,5(10)-triene	HMDB
3,17a-Dihydroxyoestra-1,3,5(10)-triene	HMDB
Epiestradiol	HMDB
Epiestrol	HMDB
Estra-1,3,5(10)-triene-3,17a-diol	HMDB
Oestra-1,3,5(10)-triene-3,17a-diol	HMDB
17alpha-Estradiol	KEGG

Chemical Formula

C₁₈H₂₄O₂

Average Molecular Mass

272.382 g/mol

Monoisotopic Mass

272.178 g/mol

CAS Registry Number

57-91-0

IUPAC Name

(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Traditional Name

(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

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

InChI Identifier

InChI=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 Key

VOXZDWNPVJITMN-SFFUCWETSA-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
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 Framework

Aromatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17160 )
3-hydroxy steroid (CHEBI:17160 )
estradiol (CHEBI:17160 )
C18 steroids (estrogens) and derivatives (C02537 )
Estrane and derivatives (C02537 )
C18 steroids (estrogens) and derivatives (LMST02010029 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

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	216 - 219 °C
Boiling Point	Not Available
Solubility	0.0039 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	31.93 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 (2 TMS)	splash10-00p0-3970000000-ea6c869f7a3556f5fb55	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00p0-3970000000-ea6c869f7a3556f5fb55	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1490000000-9f16d080d50dcea52de4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0udr-2279400000-cea6d26f1ab9c44b5160	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 (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_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0090000000-1ba1e242ed699b46bf67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-7900000000-0dae6df990a37c6c3fb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-8900000000-956bcdeac1a836c6b83c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0190000000-452a42851493e9ce5c80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0690000000-71ce13a2bfc9d4213bb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0090000000-2f90ef030c1d0edf8ad0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-abcf1c18fabe5707d6dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-004j-0930000000-a22a631636419abce8d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-a3dd3e1428abd9a33604	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00dj-0690000000-8ffd5ef2044d03b46720	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-7155e44ebc26fe65b901	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0090000000-86e488508b64b443756f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0690000000-2e46725f97f4019883a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0090000000-6ced41e08d82a4b04630	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0590000000-4d9df1569ae569967694	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004u-4690000000-661cc510ebfd4c2a2465	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-d0a3fa240c972ee299db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-5e0ebfacd0ec2ed930f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-0090000000-da2f1bf0efabdae03188	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-75c81b9a2f86b3e98ca7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i1-0690000000-f9708f269ca012832fdc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05dj-3910000000-ae2ec96914444b71ca58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-fb43b1971567fc332aa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-28ae91cf9a3f37856adb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-0090000000-325f0a631253fd5784bb	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-2950000000-9cd3211b8fd922d6f32b	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

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000429

FooDB ID

FDB112198

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5418

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

Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12115026

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16042770

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24564600

4. Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43.

5. Corbier P, Roffi J, Rhoda J, Valens M: [Female sex behavior of male rats castrated at birth and given female sex hormones: effects of hour of castration]. C R Seances Acad Sci III. 1981 Nov 23;293(11):649-54.

6. Vic P, Garcia M, Andre J, Humeau C, Rochefort H: [Early effect of estradiol on ultrastructure of chromatin in the endometrium and hormone-dependent mammary tumors]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Jul 17;287(3):141-4.

7. Salat-Baroux J, Scemama-Kestenberg H, Couturier JY, Firmin C, Agnes E, Levy G, Vuillard E: [Postovulatory hormones in plasma, peritoneal and follicular compartments]. J Gynecol Obstet Biol Reprod (Paris). 1982;11(4):447-56.

8. Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR: Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology. 2006 Sep;147(9):4132-50. doi: 10.1210/en.2006-0113. Epub 2006 May 25.

9. Stout MB, Steyn FJ, Jurczak MJ, Camporez JG, Zhu Y, Hawse JR, Jurk D, Palmer AK, Xu M, Pirtskhalava T, Evans GL, de Souza Santos R, Frank AP, White TA, Monroe DG, Singh RJ, Casaclang-Verzosa G, Miller JD, Clegg DJ, LeBrasseur NK, von Zglinicki T, Shulman GI, Tchkonia T, Kirkland JL: 17alpha-Estradiol Alleviates Age-related Metabolic and Inflammatory Dysfunction in Male Mice Without Inducing Feminization. J Gerontol A Biol Sci Med Sci. 2017 Jan;72(1):3-15. doi: 10.1093/gerona/glv309. Epub 2016 Jan 24.

17a-Estradiol (CHEM003788)

Structure for CHEM003788: 17a-Estradiol