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

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Synonym	Source
(+)-3,17b-Estradiol	HMDB
(+)-3,17beta-Estradiol	biospider
(17b)-Estra-1,3,5(10)-triene-3,17-diol	Generator
(17beta)-Estra-1(10),2,4-triene-3,17-diol	biospider
(17beta)-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
(17Β)-estra-1,3,5(10)-triene-3,17-diol	Generator
(17β)-estra-1,3,5(10)-triene-3,17-diol	Generator
1,3,5,(10)-Estratrien-3,17β-diol	biospider
1,3,5-Estratriene-3,17-beta-diol	biospider
1,3,5-Estratriene-3,17β-diol	biospider

Showing 1 to 10 of 192 entries

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

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

Showing 1 to 10 of 14 entries

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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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

Showing 1 to 3 of 3 entries

Enzymes

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Name	Gene Name	UniProt ID
Cytochrome P450 2D6	CYP2D6	Q6NWU0
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Estrogen receptor	ESR1	P03372
Estrogen receptor beta	ESR2	Q92731
Nuclear receptor subfamily 1 group I member 2	NR1I2	O75469
Sex hormone-binding globulin	SHBG	P04278
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-10	UGT1A10	Q9HAW8
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310