Showing Compound Estradiol (FDB000362)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:32 UTC

Update date

2019-11-26 02:54:40 UTC

Primary ID

FDB000362

Secondary Accession Numbers

FDB030279

Chemical Information

FooDB Name

Estradiol

Description

Estradiol, also known as estradiol-17beta or 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, estradiol is considered to be a steroid lipid molecule. Estradiol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estradiol is a potentially toxic compound.

CAS Number

50-28-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(+)-3,17beta-Estradiol	biospider
(17beta)-Estra-1(10),2,4-triene-3,17-diol	biospider
(17β)-estra-1,3,5(10)-triene-3,17-diol	Generator
1,3,5-Estratriene-3,17-beta-diol	biospider
1,3,5-Estratriene-3,17β-diol	biospider
1,3,5,(10)-Estratrien-3,17β-diol	biospider
17-beta-Estra-1,3,5(10)-triene-3,17-diol	biospider
17-beta-Estradiol	biospider
17-beta-Oestra-1,3,5(10)-triene-3,17-diol	biospider
17-beta-OH-Estradiol	biospider
17-beta-OH-Oestradiol	biospider
17β-Estra-1,3,5(10)-triene-3,17-diol	biospider
17β-Estradiol	biospider
17β-Oestra-1,3,5(10)-triene-3,17-diol	biospider
17β-Oestradiol	biospider
17beta-Estradiol	biospider
17beta-Oestra-1,3,5(10)-triene-3,17-diol	biospider
17β oestradiol	Generator
17β-estra-1,3,5(10)-triene-3,17-diol	Generator
17β-estradiol	Generator
17β-oestradiol	Generator
3,17-β-Oestradiol	biospider
3,17-beta-Dihydroxy-1,3,5(10)-oestratriene	biospider
3,17-beta-Dihydroxyestra-1,3,5(10)-triene	biospider
3,17-beta-Dihydroxyoestra-1,3,5-triene	biospider
3,17-beta-Estradiol	biospider
3,17-beta-Oestradiol	biospider
3,17β-Dihydroxy-1, 3,5(10)-oestratriene	biospider
3,17β-Dihydroxy-1,3,5(10)-estratriene	biospider
3,17β-Dihydroxy-1,3,5(10)-oestratriene	biospider
3,17β-Dihydroxyestra-1,3,5-triene	biospider
3,17β-Dihydroxyestra-1,3,5(10)-triene	biospider
3,17β-Dihydroxyoestra-1,3,5-triene	biospider
3,17β-Estradiol	biospider
3,17beta-Dihydroxyestra-1,3,5-triene	biospider
3,17beta-Dihydroxyestra-1,3,5(10)-triene	biospider
3,17beta-Dihydroxyoestra-1,3,5-triene	biospider
3,17beta-Estradiol	biospider
cis-Oestradiol	biospider
D-3,17-beta-Estradiol	biospider
D-3,17-beta-Oestradiol	biospider
D-3,17β-Estradiol	biospider
D-3,17β-Oestradiol	biospider
D-3,17beta-Estradiol	biospider
D-3,17beta-Oestradiol	biospider
dihydro-Theelin	HMDB
Estraderm tts	HMDB
Estradiol, INN, USAN	db_source
Estrogel hbf	HMDB
Oestra-1,3,5(10)-triene-3,17-beta-diol	biospider
Oestra-1,3,5(10)-triene-3,17β-diol	biospider
Oestra-1,3,5(10)-triene-3,17beta-diol	biospider
Oestradiol, BAN	db_source
Progynon dh	HMDB
β-estradiol	Generator

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

Chemical Formula

C18H24O2

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

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

Isomeric 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

Average Molecular Weight

272.382

Monoisotopic Molecular Weight

272.177630012

Classification

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 )

Ontology

Physiological effect

Health effect:

Observation:

Bleeding

Health condition:

Benign gynecological disease

Gastrointestinal disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Signaling molecule

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 79.37%; H 8.88%; O 11.75%	DFC
Melting Point	Mp 178°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.0036 mg/mL at 27 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	4.01	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	[a]18D +78 (EtOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-075a-2920000000-10218bfa5b56f829853e	2014-09-20	View Spectrum
GC-MS	Estradiol, 2 TMS, GC-MS Spectrum	splash10-017r-1791100000-7b16254894cdcb8ee86d	Spectrum
GC-MS	Estradiol, non-derivatized, GC-MS Spectrum	splash10-00di-1980000000-b2dec84718861de189ec	Spectrum
GC-MS	Estradiol, non-derivatized, GC-MS Spectrum	splash10-00di-3940000000-f3692a81f624f15d3e0b	Spectrum
GC-MS	Estradiol, non-derivatized, GC-MS Spectrum	splash10-00di-0960000000-be4e96105398cb805cd9	Spectrum
GC-MS	Estradiol, non-derivatized, GC-MS Spectrum	splash10-00di-0790000000-5c858378c15135811824	Spectrum
GC-MS	Estradiol, non-derivatized, GC-MS Spectrum	splash10-017r-1791100000-7b16254894cdcb8ee86d	Spectrum
Predicted GC-MS	Estradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-1490000000-9f16d080d50dcea52de4	Spectrum
Predicted GC-MS	Estradiol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udr-2279400000-cea6d26f1ab9c44b5160	Spectrum
Predicted GC-MS	Estradiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estradiol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estradiol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estradiol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estradiol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estradiol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-05fr-0590000000-1dd83cbcb3d21edfbdbd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-2900000000-f3279d6cdab9cf3800fd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-8900000000-0efe28378f612aab8c3d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-00di-1980000000-b2dec84718861de189ec	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-00di-3940000000-f3692a81f624f15d3e0b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-00di-0960000000-be4e96105398cb805cd9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00di-0790000000-5c83456da6e28375ad51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0490000000-c3c4658cfae36bedff30	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0960000000-d2ee002f4c0363c04e83	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0960000000-2ad7c6e17386448419df	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-f73a7a19d55a4f78be01	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0a4i-2900000000-a22a9233ffbb9eb05a1b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0a4i-1900000000-51d28e077b0aefa6aa1c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-002b-0930000000-c177eb564c729479f2be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0190000000-b572b380a16bb1b20b27	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0960000000-d2ee002f4c0363c04e83	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0090000000-f906ca4989738e61667a	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0190000000-2924fb687c668eb8918a	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0590000000-53eccf4b813f6992d38d	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6890000000-c399a267a752cfdba323	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-274ccc6305612709fd33	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-afc94cc62691bfb34161	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-0190000000-8d49a19142b1bd1a09a1	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16469

Phenol-Explorer ID

Not Available

DrugBank ID

DB00783

HMDB ID

HMDB00151

CRC / DFC (Dictionary of Food Compounds) ID

BBB24-E:BBB29-J

EAFUS ID

Not Available

Dr. Duke ID

ESTRADIOL|17-BETA-ESTRADIOL|ESTRADIOL-17-BETA

BIGG ID

36456

KNApSAcK ID

Not Available

HET ID

EST

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Estradiol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
estrogenic			DUKE
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE

Enzymes

Name	Gene Name	UniProt ID
UDP-glucuronosyltransferase 2B28	UGT2B28	Q9BY64
Estrogen receptor beta	ESR2	Q92731
UDP-glucuronosyltransferase 2B4	UGT2B4	P06133
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 2B10	UGT2B10	P36537
UDP-glucuronosyltransferase 2B7	UGT2B7	P16662
UDP-glucuronosyltransferase 2B15	UGT2B15	P54855
UDP-glucuronosyltransferase 2A1	UGT2A1	Q9Y4X1
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656
UDP-glucuronosyltransferase 1-8	UGT1A8	Q9HAW9
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-10	UGT1A10	Q9HAW8
UDP-glucuronosyltransferase 2B17	UGT2B17	O75795
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224
UDP-glucuronosyltransferase 1-5	UGT1A5	P35504
UDP-glucuronosyltransferase 2B11	UGT2B11	O75310
UDP-glucuronosyltransferase 1-7	UGT1A7	Q9HAW7
Sex hormone-binding globulin	SHBG	P04278
Nuclear receptor subfamily 1 group I member 2	NR1I2	O75469
Estrogen receptor	ESR1	P03372
UDP-glucuronosyltransferase 2A3	UGT2A3	Q6UWM9
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Cytochrome P450 2D6	CYP2D6	Q6NWU0