ChemFOnt: Showing chemical card for 17β-estradiol (CFc000337535)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:31:22 UTC

Chemfont ID

CFc000337535

Molecule Identification

Common Name

17β-estradiol

Definition

Estradiol, also known as estradiol-17beta or estrogel, belongs to estrogens and derivatives class of compounds. Those are steroids with a structure containing a 3-hydroxylated estrane. Thus, estradiol is considered to be a steroid lipid molecule. Estradiol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Estradiol can be found in a number of food items such as italian oregano, lemon balm, lowbush blueberry, and jerusalem artichoke, which makes estradiol a potential biomarker for the consumption of these food products. Estradiol can be found primarily in blood, cerebrospinal fluid (CSF), saliva, and urine, as well as throughout most human tissues. In humans, estradiol is involved in a couple of metabolic pathways, which include androgen and estrogen metabolism and estrone metabolism. Estradiol is also involved in a couple of metabolic disorders, which include 17-beta hydroxysteroid dehydrogenase III deficiency and aromatase deficiency. Moreover, estradiol is found to be associated with benign gynecological diseases and menstrual cycle. Estradiol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips, and a feminine pattern of fat distribution in women and is important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus, and vagina during puberty, adulthood, and pregnancy. It also has important effects in many other tissues including bone, fat, skin, liver, and the brain. While estradiol levels in men are much lower compared to those in women, estradiol has important roles in men as well. Aside from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species . Estrogen mediates its effects across the body through potent agonism of the Estrogen Receptor (ER), which is located in various tissues including in the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain. Estradiol binds to both subtypes of the Estrogen Receptor: Estrogen Receptor Alpha (ERα) and Estrogen Receptor Beta (ERβ). Estradiol also acts as a potent agonist of G Protein-coupled Estrogen Receptor (GPER), which has recently been recognized as a major mediator of estradiol's rapid cellular effects [A31620].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17beta)-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta Oestradiol	ChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
17beta-Oestradiol	ChEBI
beta-Estradiol	ChEBI
cis-Estradiol	ChEBI
Estradiol-17beta	ChEBI
Climara	Kegg
Divigel	Kegg
Estrace	Kegg
Estraderm	Kegg
Estrasorb	Kegg
Estring	Kegg
Estrogel	Kegg
Innofem	Kegg
Vagifem	Kegg
Vivelle	Kegg
(17b)-Estra-1,3,5(10)-triene-3,17-diol	Generator
(17Β)-estra-1,3,5(10)-triene-3,17-diol	Generator
17b Oestradiol	Generator
17Β oestradiol	Generator
17b-Estra-1,3,5(10)-triene-3,17-diol	Generator
17Β-estra-1,3,5(10)-triene-3,17-diol	Generator
17b-Oestradiol	Generator
17Β-oestradiol	Generator
b-Estradiol	Generator
Β-estradiol	Generator
Estradiol-17b	Generator
Estradiol-17β	Generator
(+)-3,17b-Estradiol	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol	HMDB
17b-Estradiol	HMDB
3,17-Epidihydroxyestratriene	HMDB
3,17b-Dihydroxyestra-1,3,5(10)-triene	HMDB
3,17b-Estradiol	HMDB
Aerodiol	HMDB
Agofollin	HMDB
Altrad	HMDB
Amnestrogen	HMDB
Aquadiol	HMDB
Bardiol	HMDB
Climaderm	HMDB
Compudose	HMDB
Corpagen	HMDB
D-Estradiol	HMDB
D-Oestradiol	HMDB
delta-Estradiol	HMDB
delta-Oestradiol	HMDB
Dermestril	HMDB
Dihydro-theelin	HMDB
Dihydrofollicular hormone	HMDB
Dihydrofolliculin	HMDB
Dihydromenformon	HMDB
Dihydrotheelin	HMDB
Dihydroxyestrin	HMDB
Dimenformon	HMDB
Diogyn	HMDB
Diogynets	HMDB
Encore	HMDB
Epiestriol 50	HMDB
Estra-1,3,5(10)-triene-3,17b-diol	HMDB
Estraderm TTS	HMDB
Estradiol-17-beta	HMDB
Estradot	HMDB
Estraldine	HMDB
Estring vaginal ring	HMDB
Estroclim	HMDB
Estroclim 50	HMDB
Estrogel HBF	HMDB
Estrovite	HMDB
Evorel	HMDB
Femestral	HMDB
Femogen	HMDB
Follicyclin	HMDB
Gelestra	HMDB
Ginosedol	HMDB
Gynergon	HMDB
Gynoestryl	HMDB
Lamdiol	HMDB
Macrodiol	HMDB
Menorest	HMDB
Nordicol	HMDB
Oesclim	HMDB
Oestergon	HMDB
Oestra-1,3,5(10)-triene-3,17b-diol	HMDB
Oestradiol	HMDB
Oestrogel	HMDB
Oestroglandol	HMDB
Ovahormon	HMDB
Ovasterol	HMDB
Ovastevol	HMDB
Ovocyclin	HMDB
Ovocylin	HMDB
Perlatanol	HMDB
Primofol	HMDB
Profoliol	HMDB
Profoliol b	HMDB
Progynon	HMDB
Progynon DH	HMDB
Sandrena 1	HMDB
Syndiol	HMDB
Systen	HMDB
Zumenon	HMDB
Estradiol hemihydrate, (17 alpha)-isomer	HMDB
Estradiol, (-)-isomer	HMDB
Estradiol, monosodium salt	HMDB
Estradiol-17 beta	HMDB
17 beta Oestradiol	HMDB
17 beta-Estradiol	HMDB
Estradiol 17 beta	HMDB
Estradiol monohydrate	HMDB
Estradiol orion brand	HMDB
Estradiol, (17-alpha)-isomer	HMDB
Estradiol, sodium salt	HMDB
17 beta Estradiol	HMDB
Estradiol hemihydrate	HMDB
Estradiol, (+-)-isomer	HMDB
Estradiol, (16 alpha,17 alpha)-isomer	HMDB
Estradiol-17 alpha	HMDB
Orion brand OF estradiol	HMDB
17 beta-Oestradiol	HMDB
Estradiol 17 alpha	HMDB
Estradiol 17beta	HMDB
Estradiol anhydrous	HMDB
Estradiol, (16 alpha,17 beta)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomer	HMDB
Estradiol, (8 alpha,17 beta)-isomer	HMDB
Estradiol, (9 beta,17 alpha)-isomer	HMDB
Estradiol, (9 beta,17 beta)-isomer	HMDB
Novartis pharmaceuticals brand OF estradiol	HMDB
Progynova	HMDB
Estradiol valeriante	HMDB
Estradiol valerate	HMDB
Delestrogen	HMDB
Progynon depot	HMDB
Progynon-depot	HMDB
Estradiol	ChEBI

Chemical Formula

C₁₈H₂₄O₂

Average Molecular Weight

272.382

Monoisotopic Molecular Weight

272.177630012

IUPAC Name

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

CAS Registry Number

50-28-2

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-ZBRFXRBCSA-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

17beta-hydroxy steroid (CHEBI:16469 )
estradiol (CHEBI:16469 )
C18 steroids (estrogens) and derivatives (C00951 )
Estrane and derivatives (C00951 )
Estrogens (C00951 )
C18 steroids (estrogens) and derivatives (LMST02010001 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0004448)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Peanut (FooDB: FOOD00016)
Hazelnut (FooDB: FOOD00376)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

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	32.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon