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Record Information
Version1.0
Creation Date2016-09-30 22:20:13 UTC
Update Date2020-06-04 20:37:45 UTC
BMDB IDBMDB0000151
Secondary Accession Numbers
  • BMDB00151
Metabolite Identification
Common NameEstradiol
DescriptionBeta-Beta-beta-estradiol, also known as beta-beta-estradiol or beta-beta-estradiol, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, Beta-beta-estradiol is considered to be a steroid lipid molecule. Beta-Beta-beta-estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Beta-Beta-beta-estradiol exists in all living organisms, ranging from bacteria to humans. In cattle, Beta-beta-estradiol is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Beta-Beta-beta-estradiol is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(17beta)-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta OestradiolChEBI
17beta-Estra-1,3,5(10)-triene-3,17-diolChEBI
17beta-OestradiolChEBI
beta-EstradiolChEBI
cis-EstradiolChEBI
Estradiol-17betaChEBI
ClimaraKegg
DivigelKegg
EstraceKegg
EstradermKegg
EstrasorbKegg
EstringKegg
EstrogelKegg
InnofemKegg
VagifemKegg
VivelleKegg
(17b)-Estra-1,3,5(10)-triene-3,17-diolGenerator
(17Β)-estra-1,3,5(10)-triene-3,17-diolGenerator
17b OestradiolGenerator
17Β oestradiolGenerator
17b-Estra-1,3,5(10)-triene-3,17-diolGenerator
17Β-estra-1,3,5(10)-triene-3,17-diolGenerator
17b-OestradiolGenerator
17Β-oestradiolGenerator
b-EstradiolGenerator
Β-estradiolGenerator
Estradiol-17bGenerator
Estradiol-17βGenerator
(+)-3,17b-EstradiolHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17b-olHMDB
17b-EstradiolHMDB
3,17-EpidihydroxyestratrieneHMDB
3,17b-Dihydroxyestra-1,3,5(10)-trieneHMDB
3,17b-EstradiolHMDB
AerodiolHMDB
AgofollinHMDB
AltradHMDB
AmnestrogenHMDB
AquadiolHMDB
BardiolHMDB
ClimadermHMDB
CompudoseHMDB
CorpagenHMDB
D-EstradiolHMDB
D-OestradiolHMDB
delta-EstradiolHMDB
delta-OestradiolHMDB
DermestrilHMDB
Dihydro-theelinHMDB
Dihydrofollicular hormoneHMDB
DihydrofolliculinHMDB
DihydromenformonHMDB
DihydrotheelinHMDB
DihydroxyestrinHMDB
DimenformonHMDB
DiogynHMDB
DiogynetsHMDB
EncoreHMDB
Epiestriol 50HMDB
Estra-1,3,5(10)-triene-3,17b-diolHMDB
Estraderm TTSHMDB
Estradiol-17-betaHMDB
EstradotHMDB
EstraldineHMDB
Estring vaginal ringHMDB
EstroclimHMDB
Estroclim 50HMDB
Estrogel HBFHMDB
EstroviteHMDB
EvorelHMDB
FemestralHMDB
FemogenHMDB
FollicyclinHMDB
GelestraHMDB
GinosedolHMDB
GynergonHMDB
GynoestrylHMDB
LamdiolHMDB
MacrodiolHMDB
MenorestHMDB
NordicolHMDB
OesclimHMDB
OestergonHMDB
Oestra-1,3,5(10)-triene-3,17b-diolHMDB
OestradiolHMDB
OestrogelHMDB
OestroglandolHMDB
OvahormonHMDB
OvasterolHMDB
OvastevolHMDB
OvocyclinHMDB
OvocylinHMDB
PerlatanolHMDB
PrimofolHMDB
ProfoliolHMDB
Profoliol bHMDB
ProgynonHMDB
Progynon DHHMDB
Sandrena 1HMDB
SyndiolHMDB
SystenHMDB
ZumenonHMDB
Estradiol hemihydrate, (17 alpha)-isomerHMDB
Estradiol, (-)-isomerHMDB
Estradiol, monosodium saltHMDB
Estradiol-17 betaHMDB
17 beta OestradiolHMDB
17 beta-EstradiolHMDB
Estradiol 17 betaHMDB
Estradiol monohydrateHMDB
Estradiol orion brandHMDB
Estradiol, (17-alpha)-isomerHMDB
Estradiol, sodium saltHMDB
17 beta EstradiolHMDB
Estradiol hemihydrateHMDB
Estradiol, (+-)-isomerHMDB
Estradiol, (16 alpha,17 alpha)-isomerHMDB
Estradiol-17 alphaHMDB
Orion brand OF estradiolHMDB
17 beta-OestradiolHMDB
Estradiol 17 alphaHMDB
Estradiol 17betaHMDB
Estradiol anhydrousHMDB
Estradiol, (16 alpha,17 beta)-isomerHMDB
Estradiol, (8 alpha,17 beta)-(+-)-isomerHMDB
Estradiol, (8 alpha,17 beta)-isomerHMDB
Estradiol, (9 beta,17 alpha)-isomerHMDB
Estradiol, (9 beta,17 beta)-isomerHMDB
Novartis pharmaceuticals brand OF estradiolHMDB
ProgynovaHMDB
Estradiol valerianteHMDB
Estradiol valerateHMDB
DelestrogenHMDB
Progynon depotHMDB
Progynon-depotHMDB
EstradiolChEBI
Chemical FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number50-28-2
SMILESNot Available
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 KeyVOXZDWNPVJITMN-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.
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
  • 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0036 mg/mLNot Available
LogP4.01HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Ovary
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified0.00001285 +/- 0.000005874 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00002350 +/- 0.000004 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00001836 - 0.00003304 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00003781 - 0.00005287 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00000220 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00000330 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00000698 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00000147 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00000400 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000121 +/- 0.0000257 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00006829 +/- 0.0000007343 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000189 +/- 0.000009913 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000308 +/- 0.00001469 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000188 +/- 0.000005507 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00118 +/- 0.000128 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00008444 +/- 0.00004626 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000477 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000600 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.0000496 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.000220 - 0.000237 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000151
DrugBank IDDB00783
Phenol Explorer Compound IDNot Available
FooDB IDFDB000362
KNApSAcK IDNot Available
Chemspider ID5554
KEGG Compound IDC00951
BioCyc IDNot Available
BiGG ID36456
Wikipedia LinkEstradiol
METLIN ID263
PubChem Compound5757
PDB IDNot Available
ChEBI ID16469
References
Synthesis ReferenceVasiljeva, L. L.; Demin, P. M.; Kochev, D. M.; Lapitskaya, M. A.; Pivnitskya, K. K. New synthesis of estradiol from androsta-1,4-diene-3,17-dione. Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1999), 48(3), 593-595.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:512140 ]
  2. Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e. [PubMed:17177502 ]
  3. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
  4. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
  5. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
  6. Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947. [PubMed:20494161 ]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively. Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid. Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen. Also displays 2-hydroxylase activity toward estrone. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP19A1
Uniprot ID:
P46194
Molecular weight:
58090.0
Reactions
19-Oxotestosterone + Oxygen + Reduced flavoprotein → Estradiol + Formic acid + Oxidized flavoproteindetails
General function:
Lipid transport and metabolism
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 (By similarity).
Gene Name:
HSD17B6
Uniprot ID:
Q3T001
Molecular weight:
36198.0
General function:
Lipid transport and metabolism
Specific function:
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity.
Gene Name:
RDH8
Uniprot ID:
Q9N126
Molecular weight:
33956.0
Reactions
Estradiol + NADP → Estrone + NADPHdetails
General function:
Involved in binding
Specific function:
Catalyzes the second of the four reactions of the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process, allows the addition of two carbons to the chain of long- and very long-chain fatty acids/VLCFAs per cycle. This enzyme has a 3-ketoacyl-CoA reductase activity, reducing 3-ketoacyl-CoA to 3-hydroxyacyl-CoA, within each cycle of fatty acid elongation. Thereby, it may participate in the production of VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators. May also catalyze the transformation of estrone (E1) into estradiol (E2) and play a role in estrogen formation.
Gene Name:
HSD17B12
Uniprot ID:
Q5E9H7
Molecular weight:
34495.0
General function:
Involved in protein binding
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. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (By similarity).
Gene Name:
ESR1
Uniprot ID:
P49884
Molecular weight:
66489.0
General function:
Involved in potassium ion transport
Specific function:
Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Increases the apparent Ca(2+)/voltage sensitivity of the KCNMA1 channel. It also modifies KCNMA1 channel kinetics and alters its pharmacological properties. It slows down the activation and the deactivation kinetics of the channel. Acts as a negative regulator of smooth muscle contraction by enhancing the calcium sensitivity to KCNMA1. Its presence is also a requirement for internal binding of the KCNMA1 channel opener dehydrosoyasaponin I (DHS-1) triterpene glycoside and for external binding of the agonist hormone 17-beta-estradiol (E2). Increases the binding activity of charybdotoxin (CTX) toxin to KCNMA1 peptide blocker by increasing the CTX association rate and decreasing the dissociation rate (By similarity).
Gene Name:
KCNMB1
Uniprot ID:
Q28067
Molecular weight:
21957.0