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4-Hydroxyestriol

4-Hydroxyestriol
Names

IUPAC name Estra-1,3,5(10)-triene-3,4,16α,17β-tetrol
Systematic IUPAC name (1R,2R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,6,7-tetrol
Identifiers
CAS Number	60021-32-1^Y
3D model (JSmol)	Interactive image
ChemSpider	168415
PubChem CID	194095
UNII	I8867W65UC^Y
CompTox Dashboard (EPA)	DTXSID20975448
InChI InChI=1S/C18H24O4/c1-18-7-6-10-9-4-5-14(19)16(21)12(9)3-2-11(10)13(18)8-15(20)17(18)22/h4-5,10-11,13,15,17,19-22H,2-3,6-8H2,1H3/t10-,11-,13+,15-,17+,18+/m1/s1 Key: KKXSCWWODCABHQ-OZPBLJIJSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4O)O
Properties
Chemical formula	C₁₈H₂₄O₄
Molar mass	304.386 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

4-Hydroxyestriol, also known as estra-1,3,5(10)-triene-3,4,16α,17β-tetrol, is an endogenous catechol estrogen and metabolite of estriol. It has been found in pregnancy urine.^[1]

References

↑ Theodore Fotsis Fotsis; Paula Jervenpee; Herman Adlercreutz (13 January 2009) [1980]. "Identification of 4-Hydroxyestriol in Pregnancy Urine". The Journal of Clinical Endocrinology and Metabolism. 51 (1): 148–151. doi:10.1210/jcem-51-1-148. PMID 6892918.

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Endogenous steroids

Precursors

Cholesterol
22R-Hydroxycholesterol
20α,22R-Dihydroxycholesterol
Pregnenolone
11β-Hydroxypregnenolone
17α-Hydroxypregnenolone
21-Hydroxypregnenolone
17α,21-Dihydroxypregnenolone
11β,17α,21-Trihydroxypregnenolone

Corticosteroids

Glucocorticoids	3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 11-Deoxycorticosterone 11-Deoxycortisol 11-Ketoprogesterone 21-Deoxycortisol 21-Deoxycortisone Corticosterone Cortisol Cortisone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Pregnenolone Progesterone Metabolites: 5α-Dihydrocortisol 3α,5α-Tetrahydrocortisol
Mineralocorticoids	5α-Dihydroaldosterone 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) 11-Deoxycortisol 11-Deoxycorticosterone 11β-Hydroxyprogesterone (21-deoxycorticosterone) 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxyprogesterone Aldosterone Corticosterone Cortisol

Sex steroids

Androgens	11-Ketodihydrotestosterone 11-Ketotestosterone 7β-Hydroxyepiandrosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione) Androstenediol Androstenedione Androsterone Dehydroandrosterone DHEA DHEA sulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α-Hydroxyandrostenedione 16α-Hydroxy-DHEA 16α-Hydroxy-DHEA sulfate Testosterone Metabolites: 3α-Androstanediol 3α-Androstanediol glucuronide 3β-Androstanediol 5β-Dihydrotestosterone 3α-Etiocholanediol 3β-Etiocholanediol Androstanetriols Androstenediol sulfate Androstenetriol Androsterone glucuronide Androsterone sulfate Dihydrotestosterone glucuronide Dihydrotestosterone sulfate Etiocholanedione Etiocholanolone Etiocholanolone glucuronide Epietiocholanolone Testosterone glucuronide Testosterone sulfate
Estrogens	Estranes: Estetrol Estradiol Estrone Estriol 17α-Estradiol 16β-Epiestriol (16β-hydroxyestradiol) 17α-Epiestriol (16α-hydroxy-17α-estradiol) 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 2-Hydroxyestradiol 2-Hydroxyestriol 2-Hydroxyestrone 4-Hydroxyestradiol 4-Hydroxyestriol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 16α-Hydroxyestrone 16β-Hydroxyestrone 16-Ketoestradiol 16-Ketoestrone Others: 27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol 4-Androstenedione 5-Androstenediol DHEA DHEA sulfate 7-Keto-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA Metabolites: 2-Methoxyestradiol 2-Methoxyestrone 2-Methoxyestriol 4-Methoxyestriol Estradiol disulfate Estradiol glucuronide Estradiol 3-glucuronide Estradiol 3-glucuronide 17β-sulfate Estradiol sulfate Estradiol 17β-sulfate Estrone glucuronide Estrone sulfate Estriol glucuronide Estriol sulfate Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)
Progestogens	Progesterone 16α-Hydroxyprogesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 20β-Dihydroprogesterone 5α-Dihydroprogesterone 11-Deoxycorticosterone 5α-DHDOC Metabolites: Allopregnanediol Pregnanediol Pregnanediol glucuronide Pregnanetriol

Neurosteroids

Cholestanes: 24S-Hydroxycholesterol
Cholesterol

Pregnanes: 3α-Dihydroprogesterone
3β-Dihydroprogesterone
5α-Dihydrocorticosterone
5α-Dihydroprogesterone
5β-Dihydroprogesterone
Allopregnanolone
Corticosterone
DHC
DHDOC
11-Deoxycorticosterone
Epipregnanolone
Isopregnanolone
Pregnanolone
Pregnenolone
Pregnenolone sulfate
Progesterone
THB
THDOC

Androstanes: 3α-Androstanediol
3α-Androstenol
7-Keto-DHEA
7α-Hydroxy-DHEA
7β-Hydroxy-DHEA
7α-Hydroxyepiandrosterone
7β-Hydroxyepiandrosterone
Androsterone
DHEA
DHEA sulfate
Etiocholanolone

Pheromones: 3α-Androstenol
3β-Androstenol
Androstadienol
Androstadienone
Androstenone
Androsterone
Estratetraenol

Others

Vitamin D: 7-Dehydrocholesterol
Calcidiol/Calcifediol
Calcitriol
Cholecalciferol

Others: 7α-Hydroxycholesterol
11α-Hydroxyprogesterone
11β-Hydroxyprogesterone
Cholesterol sulfate

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Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole) Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Lavender oil Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan) Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone) Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Steroid-like (e.g., deoxymiroestrol, miroestrol) Stilbenoids (e.g., resveratrol, rhaponticin) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators: ERX-11 Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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See also

References